The Letterman Podcast · Episode 190

Dave on Billy On The Street! Ritch Duncan Was There, And A Whole Lot More!

March 27, 2026 01:30:02
190 Dave on Billy On The Street! Ritch Duncan Was There, And A Whole Lot More! YouTube episode artwork

Episode 190 – Ritch DuncanThis week’s guest is Ritch Duncan — comedian, writer, former Weekend Update joke contributor, and one of the founders of Deathbed, the wonderfully twisted horror platform created by comedy writers.Ritch and Mike have a fantastic conversation about how Ritch found his way into stand-up, his time going to school in Indiana, and the enormous influence David Letterman had on him creatively. They also dig into his work with the Stangle Brothers before they became head writers for Letterman, and the path that eventually led him into some truly memorable corners of the comedy world.That includes being on hand for Dave’s unforgettable Billy on the Street segment, shot and featured on Late Show just before Dave retired.Ritch also shares the origin story of Deathbed, which he co-founded with Ben Zelevansky and others, and talks about the unique creative lane it occupies — where comedy writers get to let their darker instincts roam. Mike and Ritch also discuss the latest story featured on the platform, written by none other than prolific Letterman writer Steve Young.To close the episode, Mike shares the full Billy on the Street clip discussed during the conversation, and we extend our sincere thanks to Worldwide Pants for the many ways they continue to support the show by allowing us to use these pieces of Letterman history.Then, as always, if you feel like doing something noble today, head over to Hello-Deli.com — the only place on Earth to get official Late Show with David Letterman merchandise, courtesy of the one and only Rupert Jee. A deli, a gift shop, a state of mind.And if this episode gave you a laugh, a memory, or even a mild smirk, please like, share, subscribe, and leave a positive comment. We continue to shamelessly ask because it works slightly better than not asking.

Episode Transcript

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You're watching the Letterman podcast with Mike Chisen, endorsed by the Hello Delhi.

Yeah, it's the Let Letterman podcast better than all those podcast about those other men. Let let the fun begin. Welcome once again to the Letterman podcast. My name is Mike Chisum. All right, we got Rich Duncan today. Okay. Now, who's Rich Duncan? He's a com he's a comic. He's a comedy writer. He's been around the New York scene for a long time. A long time. And has worked on all sorts of stuff. Um, there's a reason why he was uh he was he was actually recommended to me by uh former uh booker for Stupid Pet and Stupid Human Tricks, Ben Zelivansky. We had a great episode last year. I love Ben. He's great, great, great guy. And um he's like, "Hey, you need to talk to Rich." Um, you know, Rich came up uh through through this the the sketch comedy culture in New York uh with The Stangles. I'm like, "Oh, okay.

That's kind of cool." Uh, the Stangles, of course, famously um headwriters for Late Show for a long time and and in my opinion um did a phenomenal job of taking things off of Dave's plate when it came to the rehearsals and things like that so we could get years and years more of Late Show um than we maybe would have. I I I appreciate what they brought to the table. Um, and so yeah, so there was that, but also throughout many of the things that he did, I mean, he worked with Colin Quinn, he was uh, you know, get faxing jokes in uh, for Weekend Update, working on all sorts of stuff with True TV. Um, there was a segment at the end of the run of Late Show with David Letterman and it was to do with Billy Iikner, Billy on the Street, and Dave did a Billy on the Street segment.

Um, he was part of that and and um, he tells the story of that day in this episode. He is also uh he and Ben and a couple other partners um have a concept called deathbed comedy uh or deathbed horror stories by comedy writers is essentially what what the premise is. Uh Steve Young has a story coming out. You can go to deathbedwriting.com and you can see that. Uh and uh we we had just a delightful conversation on the influence of Letterman, some of his brushes with people on the show and then of course that segment with Billy Iikner. The Letterman podcast has one sponsor, one sponsor only, and that is hello-delly.com. That's right, hello-delly.com. What's the Hello Deli? Well, of course, Rupert ran the Hello Delhi for years and years and years and years and years and decades, and uh was the sidekick to Late Show with David Letterman. Uh Rupert G, of course. Um you can still go to hell-dell.com and you can get mugs and shirts and official Late Show with David Letterman merchandise.

Uh just I love doing this show. So passionate about it. Thank you for everybody who uh keeps responding and uh keeps it going. Really, the community is what keeps this thing going for me. I just adore it. The stories, you could tell the uh enthusiasm that both Rich and I have for this and many other subjects around the world of comedy, show business, and of course, the influence of David Letterman. Please enjoy this episode with Rich Duncan.

Rich, I am so excited to have you on the Letterman podcast today for a variety of reasons, a plethora of of reasons here. Um, you are part of one of one of my very favorite uh segments at the end of of Dave's run. Um, the Billy on the Street segment, but there's so much more. We're going to talk a lot about that. You've been writing comedy for a long time. Um, thank you so much for coming on the Letterman podcast. Born and raised in Indiana, right? actually born and raised in Massachusetts. Went to college in Indiana.

Oh, went to I'm sorry. Went to college in Indiana. Um, always influenced by Dave. Is that that that's

Absolutely. Yeah.

Yeah. Absolutely. Very I don't think it's an exaggeration to say that that Dave Letterman

taught me in large measure h how to be funny, the attitude behind being funny. that and I say Bloom County by Burke Bri are probably the two giants in my uh in my in my comedic uh uh but I you know what I I could also see that uh everybody who comes on here probably is no one's like what Letterman he stinks you know.

Yeah. Well,

no just just the the I can't overestimate the uh the the influence that he had on my work.

Yeah. I mean, and vote like seeing him in Vancouver a couple weeks ago, I got a chance to to meet a whole bunch of people who were influenced by him and a whole bunch of different generations from a whole bunch of different uh spots in life. And and and the thing that the sensibility and the vocabulary seem to be the things that people talk about more than anything that there's Letterman words or or Letterman deliveries for jokes or or just a skew ways of looking at the world. Um you know, the sensibility that comes from that. Uh so so what made you choose if you uh raised in Massachusetts decided to go to college in Indiana? What made that choice?

Uh I I really was honestly just uh ready to get out of New England. I mean I had grandparents in in Maine and I grew up in Massachusetts and we went back and forth to my grandparents house in Maine and I was really eager to uh see the world. And unfortunately uh I ended up in Indiana.

Well that's

which is lovely. I'm not I'm not I'm not slamming Indiana. Indiana's great. I will say that when we really wanted to have fun, when we really wanted to cut loose, you know what we do? Go to Ohio.

Um, okay. Uh, when did the when did Okay. The love of standup obviously there from when you were a kid. It's safe to say that. Okay. Uh, when did you know and it's obvious that you are not just a comedy writer, but you are a stand-up as well. The delivery is there. You've got you've already got the poise. You can tell right now. Never mind the humor. You've got that as well. Uh, when did you make that step. I know you did some radio stuff in college, but did you did you do standup at the same time?

Uh, I started standup uh the summer. I believe it was the summer before or the summer after I went to college, but I was one of those guys that, you know, for for years, walked around with a, you know, had a notebook with jokes in it that I was just terrified to let anybody know that I wanted to do this. Um, you know, I came up during uh the '8s standup boom when I that was when I was a kid

and I was kind of, you know, um really attracted to uh just the style and and you know, how how clean it was and you know, the the the Giants at the time, the you know, uh Carlin and Cosby and uh Bill Hicks was big for me.

Absolutely.

Um

Stephen Massachusetts, right? Big in Boston. I mean

I mean Steven Wright was so good that it was he almost is like not I mean you know you can look at him as a joke writer and say oh this is how you write a great joke but his combination of persona and lethal jokewriting it almost made him not a an influence because nobody could do that. I mean it's like you know what I mean like it's like if I was a murderer I'd like to kill people like Bigfoot but I'm just not built that way. Like Stephen Wright was a just a jokewriting machine and did it in such a way that he was able to get up on stage and be so odd that he would unsettle people, you know, um but then would deliver something so relatable in that style. And you know, so that was I mean, in terms of I would say I'm saying that Stephen Wright is is impossible to use as someone who um directly influenced me, but he certainly made the art of standup appealing. I mean, we all had that uh the album. It was the Eye of a Pony album.

Um

and it was and that I mean, you would just

and I mean, it's it's very different in this era now where there's so much content all over the place. I mean, you know, there was very, you know, I'm not saying to say there was very little, but if you wanted to get standup content, you had to go out and buy it. You had to find somebody who had the tape. You had to, you know, so we would listen to these things over and over and over and over again. And um, yeah, Stephen Wright, fantastic. And I just love also just being a guy from New England, you can you can hear that Boston accent. It never went away. It's that Boston accent, you know. So, uh, yeah, Steven Wright's great.

On Rogan's podcast, he'll many times talk about growing up there. um he he grew up in in Newton I think it was and and he would talk about the comedy scene um in in in Boston in particular of course and and some of these people that came up and that unique voice that you were talking about all these killers that were there but yeah we're in a time where I mean people really at the end of the day if they were looking for new standup comic I mean A&E you know evening at the improv and things like that where was one of the things every once in a while you'd see comedy specials HBO did their you know but again few and far between compared to right now um very blessed has to grow up in that time and place when it comes to that. I I I would say

sure I mean um you know MTV's halfhour comedy hour was a big influence of mine. Um you know another actually someone who influenced me a great deal who also was influenced by Letterman was John Stewart. I used to love uh he was the host of Short Attention Span Theater back in the day which I believe was on Comedy Central if it was might have been Laa Network back then. Um, but it was it was John Stewart and Patty Rosboro would host short attention span theater and they basically did standup comedy clips and sketch comedy clips the same way like an MTV VJ would do it. And it would just be it was just these lineup of great jokes and and great comics. And it was just a great way to figure out not only how to tell a joke and the different ways to tell a joke, but the the attitudes and how much persona had to do with it, you know. Um, so yeah, I mean I I remember I when I first came to New York, I had a I took a standup comedy class from a comedian named Eric Kornfeld and he dropped at a certain point that he was married to Patty Rosboro. And I thought and I'm starruck. I'm just absolutely starruck.

And I had a joke. The joke was was not great. It was uh

God. I mean, what was the joke? Now I'm I'm gonna blow it. But it was um it was something like I had such a small apartment. Um you know, I I looked over and saw like Anne Frank was hiding in the corner or something like it was I mean I'm it sounds it's not a joke one would do today. Um for a million reasons. Uh, but I like and I'm and I'm butchering my own material from 30 years ago, but I remember Eric Kornfeld told me he said, "Oh, Patty heard that and was laughing so hard." And I just was

It's like, you know, when you start out and you're a young comedian or even in the first 10 years of doing standup,

a little scrap like that, you can live on that for months. Like you know somebody I remember very vividly somebody told me once when I started out doing standup I did a bit and they said Todd Barry was standing in the back and Todd Barry had said quietly during my set that's funny like

and someone relayed that to me. I was you know I mean and this is the thing this is this is where my comedy nerd you know uh thing comes in there where it's like you know uh I get starruck by Todd Barry and Patty Rosbbor. These are the people that I that I you know uh so um but yeah no it doesn't take much uh you know when you are coming to New York or wherever it is you go you know to find your community of people and I feel like in my era it was very much go to New York City go to the you know go to bigtown but I feel like in this era it very much could be find my YouTube community find my social media community find my online community you know there's Tumblr people out there that you Vine people out there that, you know, talk about these are the places that they found their comedy community. Oh, and before I forget, you talked about Letterman, how people used to uh uh talk like Letterman, I want to shout out uh a comedian I came up with who was great. Uh her name was Peggy O'Brien, and she used to in the middle of her sets, she'd just sort of stop and she'd say, "Uh, so are you like me? Do you talk like Letterman?"

And we all did. Of course we did. You know, I mean, that's one of those ones that like every comedian in the back of the room is going to roar at and

maybe the crowd will like it, maybe they won't, but you know, those are the comedians that I'm drawn to.

Oh, man. And I and I mean, like, again, this is the the the vocabulary that shows up. Are you are you like me? And I hope to God that you're not. You know, I pray to God that you're not. That that that's so many people that's just part of their everyday language. It's it the influences so much. I want to go back to uh John Stewart for a second. Um because when you think about how he started his shows and I mean I I go back as comfort food sometimes I'll go back and watch some of these things that are so uh important to me and and and what a time and place that we live in now where it's not a matter of having to dig a VHS tape out of a out of a you know an old box at the parents house because I know I recorded this. No, we've got the gift of YouTube where we can go back and watch some of these gems. You think about the shows that John Stewart did. Um, you know, he had his little deal with Worldwide Pants for a while and and and and and was definitely moving in that direction, but you think about those shows with the puppet, you know, Howard as the as as the co-host and the the puppet stuff.

Oh,

and and it was just it was so inventive and so fun yet at the same time had that same sort of

the the edge of cynicism, you know, and then of course the edge of weird and the edge of of silly and esotent. uh esoteric um and and and you felt like you were part of the club still, but just in a new way. And I go back to his last show on I believe that was the MTV show where where Dave was his guest. He was the final guest on the final show. And one of the things that Dave said to him

Oh, now I got to YouTube that.

Oh. Oh, it's Yeah. Get watch the whole episode. It's so good. And one of the things that Dave said to him is don't uh I'm going to butcher the quote, but it's it's it's don't mistake cancellation for failure. And and boy is that true. Especially if you were to look at that run of however many shows it was. It's a the creative output

of those shows and and people today they think of John Stewart as the giant that he is and who he built in himself up into um you know from the Daily Show and and whatnot. But but he was doing a lot of stuff that was really really creative back then. And as a standup his delivery was again you'd bring up you know Stephen Wright his own voice. You almost can't imitate that. It's it's one of those things where you know I think about Mitch Hedber like you can't im you can't nobody could ever be another Mitch Hedber like he's just right they're they're that unique. Um and talking about John so I love that influence but you're right I've been doing standup locally uh because not because I have any aspirations to be a standup uh nor do I even think I'm that funny but I want to get the discipline down. I was always the guy um in my family who people would be like oh the the wedding needs an MC. Okay, grab Mike to do that or or they need a you know my father passed away last year and it was just assumed that I was going to be the guy that kind of ran you know that's the ceremonies that went with that as well.

Was that you growing up or was it the radio uh that really brought that out of you? I mean, uh, I had a lot of there were there were in my family several funny people, you know. My dad was funny, my grandfather was funny, you know. So, um, I I was I was definitely, you know, one of the people that, you know, my great aunt Ellen was really funny, you know, like there were there were people that were funny. And so, um, to a huge extent, you know, a lot of the the sense of the humor there was, I want these people to think I'm funny, you know, I mean, you know, like, um,

and so so it was trained a lot in in that way. And,

you know, and and a lot of times it was the it was the subtext behind it. I mean, you know, the context of comedy when you hear it and where you hear it and how it's delivered and what medium it's delivered on

is so important to its ability to land. Um, which is really what I think made Letterman so extraordinary because what what Letterman was able to do, and this is not going to come as a surprise to any of the listeners of this podcast, but it it was he was able to encapsulate the two contrasting ideas that show business was great and show business was [ __ ]

Absolutely. Yep.

At the same time. And you know, I mean, you want to talk about like the David Letterman like joke, the perfect quintessential David Letterman joke to me is him sitting behind a desk, taking a pencil, dink, dink, dink, dink, dink, on the on the mug, right? And he just stops and he looks and he says, "You know what? This is the only thing on CBS right now."

And that's a joke you can't do today. That's a joke that in context, if you go back and you look at it on YouTube, you know, like my kid's not going to have any idea how valuable that real estate on CBS was, how much fighting there was. And by making that gesture,

the the substance of the joke, I mean, it's funny cuz like he's doing a funny face and he's, you know what I mean? Like,

but the idea the idea that this thing with all of this money and all of this fame and all these celebrities and all these things

is is [ __ ]

Yeah.

You know, but but not in such a way that it's a punk rock thing that he's going to smash the set and burn it down and and not be back the next day. It still is a way, you know, it still is the medium that brought Johnny Carson, that brought, you know, the the comedic heroes that we've seen that has taken us from our living rooms into other worlds and other places. Um, and that that can coexist with [ __ ] Gilligans Island.

Absolutely. And now and nowadays, you know, there isn't I mean, I find that uh you could get in the 90s particularly, you could get a lot of uh there was there was a lot of um traction you could get comedically by just pointing out that you knew something was hack, that you knew something was bad, that you knew something was tacky. And nowadays, I mean, my, you know, I will, uh, you know, criticize some pop star or something that my daughter likes and I, and I'm I try to be uh, as open as I can about my daughter's music. My father was not good about embracing mine. But the but my daughter will will say like, I'm such a hater, you know, and there really is no reason in 2026 to be a hater because you have options. You can turn the not even I just was almost a dial. You know what I mean? Like but there's

Yes.

You know which is anything. You can scroll to anything and past anything.

Yeah. And you know um when people criticize young people when they say, "Oh, all they're doing is staring at Tik Tok." They're not staring at Tik Tok. They are curating at warp speed. I mean look at a kid like look at a kid going through Tik Tok and it's like the way the thumb goes like that's saying this is worthwhile. this is not worthwhile and and knowing immediately what that is. And I guess you could look at that and and criticize that. I mean, it's it's, you know, it's the it's the channel flipping of of the 2020s. When the pendulum swings the one way, though, uh there's always, in my opinion, always going to be a group, whether it's a small group or a big group, whatever, that enjoys where the pendulum isn't at that moment. And and to me that was Dave like like you talking about this there's a moment that I go back to. I remember when

my friends and I and I mean we're talking we're in elementary school at this point when this happens. Okay. And we're thinking that Billy Idol is one of the hottest, coolest [ __ ] in the whole world. He is like badass and all of these things. And he's going to be on late night and we see him on late night and we look at Dave sitting there in a sport coat and just looking over him going, "Oh, your parents must be very proud." and you're LIKE, "OH MY GOD." LIKE, LIKE THAT. To me, when he was able to let the air out of balloons like that, um, and and and show you kind of that perspective that you're talking, that's the cool thing. And to me that was always um the beautiful contrast between the Tonight Show and Late Night was you know

Dave was that if you want to I don't know if it goes so far to call it punk rock but indie for sure indie rock like and then the breaking of the fourth wall of the you know the inmates uh you know a bunch of bunch of a bunch of yahoos were given access to a television studio feeling um and and and and that where we are going to take it seriously uh in our production in the things that that that that go on but We're not going to take it seriously when it comes to, you know, the the pomp and circumstance or the the the gaga the valley who all around us. We're we're we're going to make fun of all of that, including the guy who right now is on top surfing the world when it comes to who is the badass out there. Yeah. No, we're going to take the piss out of that, too. Um, and that was one of the things that I love and to this day that I love about it. Um, that I think Dave, you know, kind of perfected that and he did it with stand-ups as well. if you look at some of the standups that he would have on late night. Um, because I know you were, I don't know if you want to call it the alt comedy movement or whatever, but you had inventive comedians. You know, I think about guys like David Cross and some of these other people that are out there that that um that were influenced by exactly what we're talking about when they were young.

Well, it's the natural extension of the people that were cool and were good and were funny.

Yeah. took took their surroundings completely into, you know, I mean, this is not a situation where, you know, you would take your vaudeville act and come in front of the mic and do your vaudeville act. I mean, the the Letterman is the institutionalization of standups like Steve Martin and Albert Brooks.

Sure.

You know, where Albert Brooks would come on and he'd do a ventriloquist that couldn't do it. and you're used to seeing a ventriloquist who can do it, you know, but like the there's a limited if you feel like this opportunity on this camera and this television show is the most important thing in the world, you're going to show up and you're not going to do, you know, and to actually say, "Well, wait a minute. What if we depict how important it is to this person and then watch him melt down?" You're operating on an entirely different level. And and what is neat about Letterman is he never disrespected the level he was on, you know, or or I mean he he elevated it

sure

by denigrating it. I mean it's it's it's some next level um

you know,

but then he has more on and and totally absolute respect

for him, his style, where he came from, all of that stuff, right? But then of course George Miller comes on or or or someone like Yes, I can totally he appreciated every single style out there. Um but the the alt stuff is is where in my opinion it got to rise because of late night.

Yeah, absolutely. Anyway, I'm glad we agree that Letterman was good.

Um were you writing back then too or or was it like what was your foray into it? Was it writing when did writing come along? Well, I mean, I I recently did a show um uh that where I I said this line in the show, but it's true. I was always the kind of comedian where I would uh come off stage and people would say uh you are such a good writer, which is like one of those one of those things like, you know, your material would be so great if it was delivered by literally anyone other than you. if um and um you know I mean um it it's uh I do feel like um what always brought me to the stage and I don't know whether it was anxiety or uh like um not uh being super self-confident in myself but I always felt like I needed to have that good joke

to be able to have the confidence to stand up and and do that. And you know, I mean,

well, I mean, I I needed I needed to have that, you know, arrow in my quiver of I know I got this good joke. So, if you know, um, and not everybody needs that. I mean, the reality of stand-up comedy is it's not a man doing funny material, it's a funny man doing material.

And, you know, so it's and you got to be lucky and good at the same time. And in my standup career, sometimes I was lucky and sometimes I was good. Not usually at the same time. I mean, I get that. you know, but I mean my, you know, in every instance, um, I mean, you know, of course when you're young, you want to be George Carlin or you want to be the standup that's on stage that does these things, but it it also as you get older, there are um, you realize that the ground shifts under you and that, you know, the guy who's the George Carlin then, you know, if the timing was different, the society and what people need at any certain point. There's so much that's not in your control. And what is in your control is your ability to create art every day. And the way I was always able to do that was writing. So that's, you know, and it it also came out, you know, like I mean I would say the emergence of Twitter helped me a lot as a joke writer. I mean back when Twitter started it was you had to do 180 characters.

So that's what I was going to say. Yeah. Okay. Yep.

Yep. you had to have an idea and it had to be within this and of course you know now they say oh just write whatever you want you know and then that the the discipline of it I mean I'm not saying I would when I was writing tweets in that way and when Twitter was actually Twitter I found the the 180 thing to be limiting for sure but I think ultimately it did make me a better jokewriter um and you know now not only do they have no character counts but they also uh the the computer will write it for Yeah. So, you know,

and that's it. I mean, that's a whole another place that we can go. But that was a question that I asked uh Steve O'Donnell when I had him on. I if if he preferred writing

with a fence and parameters or whether he preferred the open field and and the the

I bet you said fence.

Yeah, the fence. I mean, you know, because they had to do they had to avoid um they had to do a lot of things to avoid any resemblance to the Tonight Show. And so there were things a lot of things they couldn't do. So the things that you can't do almost opens up more creativity because now you got to problem solve. Now you got to think around that. Right. And I think Twitter's a phenomenal example of that. How about the collaborative process when it comes to writing? Do you uh collaborate uh or or do you prefer to do it yourself?

Uh I I like to uh uh I like both, you know? I mean I'm doing uh Deathbed now, which is horror stories for comedy writers. and and I used to do uh I I I in the early 2000s I started a humor magazine called Just Magazine uh where we would do short humor pieces in the vein of uh Spy and the Old National Ampoon.

Um and I really love the collaboration of working with an author that'll come to me with something and being able to say, "Oh, this is, you know, this is the part that I like about this." And having and having that collaboration. Um, I also find collaboration to be great in terms of I have a really hard time uh summoning the ego to promote myself, right? And if I were to say like I I have this whatever I have a a website that tells horror stories by comedy writers. If I said, "Hey, I'm a comedy writer and I'm doing all of Rich Duncan's horror stories." I I would feel it my immediate instinct is, "Well, why why would anybody care about you?" Right? But when I say these are horror stories by comedy writers, I can say, "Hey, here's a whole community that I'm getting together." And if you can tell a joke, you can master the concept of tension and release. And that's also how horror works. That's how comedy works.

These people are good at this. Let's, you know, and then what I can do is I for me promoting others just comes so naturally. It's so easy for me to, you know, I mean, whatever. Like the, you know, when I talked about Peggy O'Brien earlier, a thousand times it's easier for me to say, "Oh, this friend of mine has a great joke." than for me to say, "Oh, well, I did this joke." I mean, earlier in the interview, I was like, "Oh, I did a joke." And I butcher it. I sucked out of telling it. But when it's somebody else's joke, it's very easy for me to do it. in terms of celebrating the community that I come out of. And honestly, I've had a lot of different comedy jobs over the years for very short periods of time, but the comedians and the writers that I've worked with and that I've been friends with and that I've been colleagues with, they've been there. They've been the ones who have helped me out. So, anything if that collaboration leads to that relationship and that relationship uh blossoms and that community blossoms, that's just going to mean everybody gets more work and everybody gets to do this

fun thing that makes the crazy go away a little easier.

I want to keep going to death here because uh the the concept to me is genius. Um really at the end of the day, it's it's uh you know, stories in the horror genre written by comedy writers. That's the premise, right? And and let's bring up Ben Zelansky. It's you and Ben came up with this. When did you and Ben meet? How long have you guys known each other?

Uh boy, I've known Ben for a very very long time. Um and for for the show. You knew him Ben?

Yeah. Uh I don't know whether I knew him when he interned for the show. I'm not sure. I know that he was we we really became good friends when um I mean we'd known each other and he'd been part of the scene. We both were friends with Chris Duca and I think maybe Duca might have worked on although Duca worked for Conan. So I don't know whether but

but I don't know whether uh whether Ben and he worked directly together but I remember

uh Ben was absolutely one of Duca's buddies and Duca knew a ton of people who were just smart funny TV insiders like you know like

Chris this we're talking about Chris Duca who's just a terrific comedy writer and a standup and

um just a good buddy of mine for years and he's just always been I always called Chris Luca like one of the best lateral comedians in the world because he like everybody can tell jokes, but he would be able to be like go to the side and be like, "Yeah, this guy's doing this." You know, like where his his masterpieces were a lot of comedians go straight forward. He would he would

he he he had that Barry Sanders juke. He could go to the side and get got the laugh that way. But um so I don't remember I I feel like Ben came to me through Duca somehow but I had done a number of like after just folded I ended up doing a lot of blogs and that's what kind of got me into social media. But one of the I did this blog about werewolves which I got internet famous and got to write a book and it was fun. But the after that had happened, the lesson I took away from it was um write about something that you want to write about. And what I really wanted to write about at that point, I was I've always been just a giant hockey fan. And so I did a blog called American Hockey fan. And the the joke there was there's only one and it's me. Um, and it was just kind of an irreverent uh sort of profanityfilled uh blog making fun of the daily NHL stuff and Ben happened to be a huge New Jersey Devils fan. So when I was doing

when we talking here

probably 2005 2006 were winning cups and stuff they were winning

oh man the Devils the Devils are still the best they're still the best value for professional sports in this town. I mean, you know, they're they they put they put a good product on the ice generally. I think they're bad this year, but um but they uh

Well, no, I mean, there's obviously ups and downs and what, but when you look at like the the the I mean, especially those years Stevens and those years were flawless. Yeah,

absolutely. I I'm I'm a gigantic like I've got a crown on my back. I'm a huge LA Kings fan and I was there for the finals in 12 and

I was there too in New Jersey.

There we go. There we go. I was down there for the LA games, but but yeah. But yeah,

I went I went to one of the games in Jersey cuz it was affordable. That's the beautiful thing about New Jersey. You can get to a I went to a Stanley Cup final game with the cup on the line

just and I think I got in for like it might I might have paid $300 for the ticket which is like

unthinkable that you could see the Stanley Cup awarded for that amount of money.

Um and u the Devils actually won that game so I did not get to see the cup awarded but it was

a phenomenal experience.

Yeah, cuz we came back to LA and won it in games six and 12. Yeah. Um, uh, is the blog still around? I need This is like, as you're describing the blog, I'm like, "Oh my god, I'm your audience. This is This is amazing. We didn't talk about that before." What was it called?

Uh, it, uh, it was called American Hockey Fan. Um, it's, you probably can find it at americanhockeyfan.blogspot.com probably. Um, we definitely had an American Hockeyfan.com alias. Um, but it I I forget why it went away, but it it definitely we definitely ran out of gas on it after a number of years, but it was fun. I mean, you know, there was a there was a fun story where I had got into a little bit of a dust up with uh the owner of the Washington Capitals, Ted Leonsus, and uh it was a little tight, a little tense, a little back and forth, but uh eventually ended up in a nice way. And he invited Ted Leansis was a big digital media guy. And so he invited American Hockey fan to go to DC and to broadcast from the broadcast booth. And uh Ben and I came out and did that together. Ben and and my wife and I uh took a trip out to DC. And um Ted was uh out of town that day. He didn't he didn't he didn't stop by and say hi.

I don't know whether he really was or not.

But not going to be a part of it.

But yeah. No, he had cuz Ted Leianis had a thing on his blog where it was like the TED list and it was like all the things he wanted to do and it was like swim with great white sharks and so we were just busting his balls for like I mean it was just to to us back in those also Ted had a blog and back in those days this is I'm dating myself like crazy but like to me in my head at that point a billionaire with a blog made no sense you know like a blog was for people like that don't have an ability to reach a wider audience and if you are a billionaire you can

buy a TV network you can you know what I mean like what are you doing on the internet you know

um so there was which of course is looking back on it uh shortsighted that's the you know I mean he was the one that that knew that that's where the technology and where the

eyeballs and ears

going as Walter Gretzky would like to say

yes yeah you got to watch for where it's going absolutely

yep yeah I uh okay so I want to get back to death so for people who want to go to death. Deathbedwriting.com is the place to go uh where where everything is. Okay. So, I want to talk about this because like Steve Young has written for this and uh

he hasn't hasn't been published yet, but I was working on it today. Yes. Steve Young, long time Letterman writer and uh wrote uh one of the a terrific Simpsons episode called Hurricane Netty. But yes, and he's great. Like Steve's been on the scene for a while. He's writing stuff for Slackjaw and uh I I got to perform with him a couple times at Kevin Geeks Out, the terrific video variety show that Kevin Mah runs and Kevin's helped us out with Deathbed 2. And so it was really through Kevin that I was able to contact Steve and

right

Steve is just I mean I'm sure you know he's another one of those guys that just has you hear his comedic voice and you go yep and you go like did he get that from Letterman? Did Letterman get it from him? Have they just been working together so long that that's what that voice is? It's and you know, you get it from like Meil Marco stuff a little bit too and some of these longtime Letterman collaborators where you're like,

you know, the attitude is is in the sauce, you know. Um, and he does that thing that great comedy writers do, which is the the detail around the premise. I feel like I am very good, if I can, you know, pat myself on the back a little bit. I'm very good at finding the bridge between the two f like two things that you don't really know why they're funny. I'm pretty good at building that bridge, but I think the great comedy writers are the ones that decorate the bridge with really fun language and Steve's just a master at that. So, it was it's been really fun. He's I I his story is called 555 and it's based on uh uh basically you know how when you uh see a phone number on a TV show or a movie the the suffix is it suffix the three letters are are 555 and that's how you know that it's it's fake and so this is about a dirt bag Hollywood producer who starts getting scary calls from a 555 number

and the the the spooky fun goes from there but he has these wonderful little details of the names of the projects that this dirt bag Hollywood producer had and one of them was like a puppet show called Hurt and Ernie.

Oh no.

You know, and just like little like and and I mean it it doesn't it doesn't have anything to do with the with the premise. It's just like oh here's just a great little punchline. This is a thing that a guy like this would have. He has the the the assistant the the the Hollywood dirt bag in this uh in this story has an assistant and the assistant name is Brian

and it's it's not Brian it's B R O Y an explained but it's LA so of course his name is Bruyan and it's just like how do you you know like you have to give the assistant a name and that's what he chose to do. So, it's it's a it's a um it's a it's a classic uh deathbed style Tales of the Crypt EC, you know, horror comics thing where you have a bad person getting their just their uh you know, in that in that fun comic booky kind of style. But it's the it's the decoration along the way, you know, that that where you can really kind of see that this is a guy who um who details matter to.

I want to uh I want to talk more about Death Bay because I'm I'm fascinated by this. I think it's a I think it's a phenomenal uh concept and I want I'll go come back to it in just a second. But before we do, I want to allow uh loud some more praise on to onto Steve. Um Steve is one of my favorite humans walking the earth. I adore him. Um, I consider him a a good friend. Um, and and and he's a guy that if I'm going through something, I'm he's a guy that I can be vulnerable with and I I can do that and I appreciate him so so so much. Um, he wrote the theme for this show which is just, you know, three or four shows in. Yeah. The the the new

interesting musical background with him too. Absolutely.

There we go. And this is where I want to talk to you about this part as well, whether we get to it. I want to do Do you want to talk about more about Death Bed? Maybe we get to this and you can remind me to PS it because I mean here's a guy as well.

Writer, writer, writer, writer, writer, writer, writer. Wait a second. Also a performer and the performer part of him is blooming and it's so fun to watch that like you know the jingle for this this this uh this show. you know, somebody the first thing that a Letterman uh a big Letterman fan who heard the jingle um said was this reminds me of uh the fat man, the strong man, and the genius theme, which Steve wrote, Paul and the band played it,

but Steve wrote it. You know, it's got kind of that rawhide sort of thing. And it's so cool to watch him, you know, cross over the bridge of saying, instead of writing this for Paul and the band, I'm going to do these musical um presentations myself and bring my own flourish to it. Um and I just love that. I love Steve. Uh, one of my favorite days ever was um was going to Steve's apartment and he's showing me some of this music uh or listen letting me listen to some of this music, showing me some of these materials that he has that haven't been released. Like you said, the voice of the show. It was like the Letterman show was was presenting things to me that had never been seen before. And I'm on his couch literally like busting a gut laughing which you know he is you know you can tell he's so satisfied from that cuz he gives you the little you know you know just as a little you know you could tell but you could tell that he was so happy with that. I got to ask you oh no we'll get to the we'll get to the um the the the writer and performer part of it and how they they can correspond in a second here. But as you're describing this all I keep thinking about is Twin Peaks. All I keep thinking about is here's one of the most um scariest things of my youth ever because when it got dark and deep, it went

to the to the wall. It went all the way. And yet some of the quirkiest, strangest things that would make me just light up in laughter and and and and the idea of of of a a horror story from the idea from from a comedy writer. Genius. Genius. I I love that you guys came up with this. I love that you're moving into this uh down this this lane here. Um and I think about like Key and Peele. I look at I look at what uh some of these movies that are coming out that are like, "Wait a second, but these guys are what? It's not supposed to be like that. It's so cool." What are some of the other Who are some of the other writers that you have uh worked with and and um and Yeah.

You mean in terms of in terms of death or

Yeah. Yeah. Uh, well, I mean, we've we have I'm I have my fingers crossed that I should have a story coming in soon, hopefully from Andre Dubet, who's a longtime Conan writer. Um, and he was a guy that wrote for me for just ages ago, and he's just got this wild creativity and uh big characters and he's also a terrific comedic performer. Um, so we have stuff from him coming in. And I had a we had a really interesting story come in from Scott Jacobson who wrote for Bob's Burgers for years.

Um and and you know the uh we had a great story from CC Pleasants who uh was one of uh Kimmel's writers for a long time and and wrote for um uh oh I'm now blanking on the uh I wanted to say Captain Kangaroo but it's not Captain Better. Let's get Mr.

No, no, it's definitely No, it's definitely not Captain Kangaroo. It's uh it's the um Bill Nye, the Science Guy.

That's where my Yes, she she wrote and Bill and Nai had it. But I mean like you know um but uh and uh she wrote the movie Bridehard, too, I believe. But anyway, but Cece's great. CeCe I I came up with doing comedy and she and uh her partner Katie Massa used to do this thing on the subway. Um it was called Subway Soaps. And Cece would burst onto the subway at 125th Street in a bridal gown in tears. And then, you know, Katie would chase through and it would be this. And this is before I think if you saw something like that now, you'd be like, "Oh, well, some idiots taping with their phone."

But in 1998, it was like, "Wait, what am I seeing?" And they would write these soap opers of like a bride gone crazy and would it would play out on the subway car between, you know, 125th Street and 59th Street on that big chunk of uh express track. And then at the end of it, they'd go through and hand out cards. what you just saw was Subway soaps. If you like this, come to our show on this thing. And it was just this really amazing creative thing. Um, so I mean, and in terms of the horror piece, it is also like some of the stories are funny, you know? I mean, um, uh, Kevin Maher, who I talked about, who's just been a fantastic collaborator of mine over the years, uh, uh, he did a a story that was a a poem. I mean, almost like a children's poem. Um, and it was about the the monster under my bed and the uh I probably shouldn't, you know, I won't give away the punch line to it, but it's it's worth reading and it is it is not what it seems as it as it goes through and it's it's it's a very uh

it I'm not even I I shouldn't um read it. It's called the monster under under my bed.

Go to death writing.com and you can you can see it right now. You can

and you can see it. Yes. And so um so I mean so really the the idea of deathbed and well I mean I also had done this blog that was about werewolves. I had written a blog years ago. I called it what is happening to me.com and the reason I came up with the idea was at the time all comedians a bunch of comedians that I admired had started blogs. They all knew HTML. They were doing these really interesting personal websites. And I got on the blogger at the time and I just didn't know how to make a website. I didn't know how to make it work. And so, uh, but what you did see back then was people pretending to be other people on social media and on Blogger and on this and that. And so I said, wouldn't it be funny to do a blog from the perspective of a guy who got bitten by a werewolf? So, you just sort of have his regular life and then, you know, you talk about how he gets bitten by a werewolf and then on the day that the actual full moon happens, you just don't write anything and then 3 days later you're like, "Yep, woke up naked at the zoo again. That was weird."

And so, I just decided to do this and it was and I ended up writing it for about four months and never had said that it was by Rich Duncan. invented. I I came up with a name Kirk Thompson and had him work in the video store that I worked at in Williamsburg, which was Real Life in Williamsburg, which is an awesome indie video store back in the day.

And um and it got popular. Um I mean, not huge popular, but you know, people were dropping notes off at the video store for Kirk Thompson. Um and you know, so and it was

talk about Lettermanesque, by the way. That's that's a per like the influence there, of course, is just you know, right in your face. Um, yeah, people were dropping off notes for Kirk at the video. Do you remember what any of the notes said?

Oh, it was just like, yeah, I hope you, you know, like whatever the, you know, I hope you work it out with that girl, you know, or or or whatever it would be. I mean, you know, um I mean I think people would like they read it and they because it also this was not I mean this was coming out every day. This wasn't like you know this is before the era of I'm going to schedule all my social media posts or my blog posts. Um, and it was even before the day of really too much curation, you know, like the way we publicized blogs was you had a blog roll of the other blogs you read and you'd go over and you'd click and you'd kind of find these things. And

there wasn't most of the blogs in that era were were very um sort of confessional. They were first person and they were confessional and they were true. And so I had taken that style of first personal and confessional and true and just added what I think a lot of great horror movies do which is the what would you really do if this happened. I mean, if you read the blog, I don't know you will, but if you ever go back and read, you know, what has happened to me at blogspot.com,

it is very much, it borrows a lot from American Werewolf in London, both horror-wise and comedically, because American Werewolf in London is the ultimate what would you really do?

Yes.

You know, like this is really, you know, this isn't, you know,

spooky gypsy lady. I mean, this is American tourist in London. if he does get bit by a werewolf, what does this kind of really look like? Yeah.

Um, and I feel like that is,

you know, the the comedic idea of just change one thing,

you know, is very compelling to me. So, you know, I was effectively,

even though I was telling a werewolf story, what I was really doing was parodying confessional blogs, you know? I mean,

so it was fun.

Two familiar things together and you're Yeah. It's it's

and and it and it was and ultimately I was doing it because I didn't know how, you know, I I tried to do a blog that was my standup and my material, but like when I did that, it was taking material from one medium and forcing it into another. And it it was fine, but I was reading you were reading jokes that were probably best performed.

Yes.

You know, so it was it was an interesting thing. And what happened with that was so neat in terms of it got optioned. it didn't get turned into a movie, but it got optioned several times and it almost became a movie and it gave me, you know, a couple thousand dollars when I needed it. Um, yep. And, um, and it led to a book deal that was, you know, we we did a I did wrote a book with Bob Powers, who also has written for Deathbed and wrote for Jest, who's a great comedy writer. Um, and uh, we wrote a book called uh, The Werewolf's Guide to Life, a manual for the Newly Bitten, which is basically um, what to expect when you're expecting if you're expecting to be a werewolf. That's basically what it is. I think it's I think the book is brilliant. I think it's long.

I think it's it's it's it's a 300 words of how to really and we took it seriously. We were like how to be a werewolf.

Um you know um and uh it's I think it came out about 15 years ago and we've almost made our advance back. So I feel good about that.

Um before we move away from deathbed because I I'm I'm fascinated. Oh, but I I I told that whole story.

Yeah. But the the the what what I really wanted to do with I mean the fact that I had had success with this werewolf project that was a effectively a comedy horror project and it kept kind of being optioned was that a we there was the success of Get Out with you know uh Jordan Peele and Zack Kger you know weapons and Barbarian just terrific horror projects are coming out from comedy people. Um, and of course, you know, the classics, the Evil Deads, and I don't need to get into all of it, but I mean the, um, that pattern had been established, but also I felt like if I did this project with this werewolf thing, and it got optioned and it led to something else, why not create some sort of a uh, a publication, a place, a destination where there could be lots of these, you know, like, you know, instead of it just being one werewolf story that takes four months to unfold slowly. What if we had short little

EC horror comics kind of stories that were like Creep Show and that you know, who knows? And the way the

the I have a a a basic release on there. So, um the stories are all owned by the writers who write them.

I think I have something in there that says uh if the thing goes on to be, you know, uh

to to great to great success or something. and you know like and it can be proven that they found about it at first on deathbed we get 2%. So the the idea is I don't even know what the number is. I don't know but I wanted to put something on there that in case

somebody did write the story that went on I mean you know and and there's a great tradition of classic horror films being based on short stories. Uh, I think it's called Who Goes There. I'm not sure. Is the the the short story that was turned into John Carpenters's The Thing or The Thing from Another World First and then The Thing.

I think it's called Who Goes There, but it was it's a it's a short story about The Thing

and you know these the precedent for um uh John Carpenters They Live was a was a short story uh first as well. So like there is a

pre fight scenes in any movie too by the way and and they live Rody Piper. Yes. Anyway,

and you know, I mean, another reason that you do a horror story in a short format like that too is because it gives a producer um room to expand upon. You know, obviously the fight scene from They Live doesn't exist in the short story, but because it is a short story and the characters are clear and the overall arc or the gist or the twist or whatever it is exists in it, you have enough that potentially someone could look at this and say, "Hey, this this could be more. You know, these characters are interesting." you know, Steve Young's, you know, dirt bag, you know, maybe there's more to Bruyan than just his name in uh in Steve Young's story possibly. Who knows? Um and ultimately the doing of it is also worthwhile, you know? So, like I mean, and that's huge. Um

I love doing standup, but there is a maddening sense of um impermanence to it. I mean, the magic of it is that it's a real person standing in front of you doing this thing. And you know, um,

I can't tell you how many times I've sort of I've looked back on my stand-up career and thought, gosh, how many ideas, how many things do I that I just don't that I can't touch anymore, that I can't, you know, that that, you know. So, what's really really nice about Deathbed is we started this started thinking about it last summer with the idea of let's pitch it before Halloween spooky season, you know, and and we wanted to basically get one horror story out a week through the whole month of October and see where that led us. And since then, we now have published about 20 original horror stories that didn't exist in the world before we did this. And you know, and there's a nice there's a nice uh blend of different kinds of horror stories there. They're not, you know, I don't know that one person would read the entire site and say, "I love all of these." You know, but but I'll bet you 10 people could read it and each one of those 10 would find two that they go, "Oh, I like that one." You know, so and we tried to do that.

It makes a lot of sense. And and again, we we're going back to collaboration and and in the creative spirit. um throwing out the the the these works and and putting something new into the world. It's such a beautiful thing. I've got a question for you when it comes to that. The idea of a free form or a poem versus do you give them and we were talking about parameters earlier. So when you have somebody who comes along and you want to say, "Okay, let's do this."

Do you give them any parameters? Is there a word count uh limit? Is there

4,000 words? Is that what it is? 2,000 words.

It's four It's It's 4,000 words. And we figure that out words. That's a chapter of a book by that's a chapter of a book basically. So,

and that's the ceiling. That's the top. I mean, and the reason the reason I do that is I mean I think I think there might be one story in there by me that might be 5,000 and I can barely get through it.

Um, you know, so like I mean I'm conscious of the fact that we're using a newsletter format. The reason we picked a newsletter format, we we publish on Ghost, which is like Substack, but if you subscribe to Deathbed, subscribe.deathbedwriting.com, deathbedwriting.com you get this horror story that shows up in your inbox uh on a regular basis and you don't have to do anything and we have uh you know by signing up we can contact our fans directly so I'm not at the beck and call of any algorithm or any you know we're we're promoting ourselves on Instagram because we kind of have to be there but it's it's frustrating you know I mean

like it's it does not feel like it did on Twitter 15 years ago where if you have a really great piece of content it can catch fire and people are going to retweet it and I mean it it might catch fire and go to a wider audience but it's not going to go wider in the way where

you know if I have a joke that is you like my followers on Twitter back in the day were you know writers for shows like Letterman and Family Guy and I mean Family Guy was like if you wrote for Family Guy that those were like the Twitter Godzillaas for some reason I don't know all all the guys that that ended up on Family Guy ended having these massive follower accounts. So, you'd get a retweet from somebody who wrote for Family Guy and it was like a big deal. Um, but like it does not feel to me like social media is interested as much in building a personal brand as much as it is interested in

finding whatever the medium level is in there that and then feeding it to people, you know? So, like and really honestly

there is more. Yep. And I'm what I'm doing here intentionally is also it's horror stories. They're gross sometimes, you know, like it's not I mean I did a one of my recent horror stories I did there was a there's a band uh called Top House and they released a song called Deathbed and they're just I don't know how popular they are but they released a song that was called Deathbed and I loved the song and so I tagged them on social media and I was like because you guys did a song called Deathbed I'm going to write a story called Top House, right? And I just thought it would be funny to to to do that. So I looked up where their band was from and I said it in their hometown and you know and I I had this this the story I had in mind that I might have wanted to write and it's been in my head for a while was the idea of a murderer who kills someone in Macy's and then can't find his way out because it's so you're frustrating.

You can't get your cannot get out of a and so that's sort of the the funny thing like you can do a horror story but like how the hell do you get out of this place? And it was just like I was in Macy's and I was trying to get out and I thought, "God, it'd be funny if I, you know, murdered someone and I had to escape to for my, you know, my freedom and I could not figure out where the goddamn exit is." So I I adapted the story and I called the top house the the top of the department store. I wrote this whole story and the band did not care. The I tagged the band, you know, and and but this this my point is I'm doing horror stories, you know. Yes, I tagged this band. I was inspired by this band. I thought it was funny, but it's also ultimately a story about a guy who stabs a woman in the neck. It's not like that's that's not like someone be like, you know, that might not be my personal brand. And I get it.

Um, but you know, I mean, what I am trying to do is

build community with other comedy writers. I feel very good about the premise behind the story and the reason that I ended up telling the story. All that stuff is fun. And so it ends up being that whether any of these stories do get optioned by somebody or turned into a movie or turned into a book or turned into a collection or a podcast or whatever they might live on as

ultimately the doing of it is

is worth it to begin with. The making of the story,

the collaborating with the writers and in some cases the artists who do the art on it. Um and um just that that process is fun. And also we are slowly building subscribers. We started with 35 subscribers and now we're up to close to 200. And it's you know there's no one I mean it the limit on it is going to be me. you know, like if I if I decide, gez, this is a really a lot of work. And I I think we actually may slow down through the summer months to one story a month just so I can kind of backload and and and build up a story library again. Um cuz one a week is is a lot. I really had sort of thought that there would be a lot more people submitting stories. Um and it is it is outreach has been a challenge. um the the people who do do them and like doing them. Um, it's always a treat, but it's also not an an insubstantial amount of work to work with the person to figure out the idea and just there there's a fair amount of emotional labor in getting in an idea that maybe isn't perfect for death bed.

you kind of have to say, well, I don't, you know, I this is great, but it, you know, we got a story in once that was a really, really interesting, cool premise, but it felt like it was was all dialogue, and it almost felt to me like I was reading

an audio play of a horror story. And so, I passed on the story and I told the writer, I think it's great,

but it's

this just isn't deathbed the way the way it is. And unfortunately, I haven't heard from that person again. And you know what I mean? So like you always are kind of balancing. So you know I I I would like to

eventually be in a place where we have enough

submissions flowing in that I don't really feel like I have to you know um work too hard with the writer or potentially hurt somebody's feelings, you know. Um and and passion projects are like that. You feel your way through it and you you learn these dynamics. you learn these uh you know where the es and flows are and you you find that balance. I love the message of the process is the outcome. Um this show is very much all that is is the process is the outcome. This thing that you do from the side of your desk but it feels good and it exercises that creative thing that's inside of us that needs to get out. Um you know the muse talking to you. Well I mean there are so many people out there who who who don't who would love to do something but they don't do it because they think the outcome isn't what they desire. Well, if the process itself is the outcome, all of these things will will figure out a way. You know, I I I feel bad that you went through the um you know, I'm a relationship guy, right?

I love relationship. And I mean, very very few times, but it's happened every once in a while where there might be a staffer who doesn't like what I do or whatever or there was some static there that always feels bad. It goes right to the heart, but at the same time, it makes it better for the next time I have uh an interaction with another staffer or something like that. Um I got to ask you this. Have you thought about asking the Stangles to uh to submit?

I mean, maybe I will now.

They just did a uh they just had a comedy class that I that they were looking at and I was I I went back and forth with them on Facebook. I forget exactly what it was that I was I I'm terrible on social media in that like I

have a a funny idea or a reply or something and I'll type it. And this actually happened uh uh I worked with this I worked with a guy named John D'vor who does a terrific site that's 150word uh movie reviews and um he had not liked uh GMO del Toro's Frankenstein and I loved it and so I had wrote written something saying like well you know taking it putting it out on Netflix didn't do it any favors and and and he's just got a great site for um back and forth with movie stuff and I get a big kick out of it and

uh he wrote me an email and he was like I didn't mean to do this, but I deleted your comment by accident. And I was like, I have this happened like a half an hour later and I was like, I already forgot I wrote it. Like I I you know, um I'm a quick draw when it comes to uh social media comments, but his

just get it out there. Yep.

So, you know, I mean what I I mean I I would love I would love it if the Stangles wanted to write a horror story. But what I've also found is that there are I I like there there is no guarantee that someone who is a comedy writer will want to write horror you know I mean I think that I think that people can I think that I think that the skills that it takes to do comedy when looking through a certain frame of you know like I mean

I wrote it in the deathbed introduction you know and and Dan McCoy who wrote for the Daily Show and uh and the Flop House podcast he's was a editor on the site And you know, I mean, he had, you know, come up with the analogy that like, you know, the the old lady that, uh, in the Three Stooges, you know, uh, short that points up at the delicate vase that's standing up on the on the pedestal and says, "Don't knock that over." That's that's the same as, you know, uh, don't, uh, you know, drink me. You know what I mean? like or whatever the you know, you know, uh don't step off the yellow brick road, you know, like whatever these, you know, and and you can play that same tension and knowing that the thing is there and you can play it for comedy and you can play it for laughs. That being said, not everybody wants to do that and that's totally okay. So, I mean, you know, what I asked the Stangles to do it, if they wanted to do it, I would absolutely I'll tell you what, if either one of the Stangles said, "I want to write a horror story.

Do you want to take a look at it?" I would read it the second it came in. I'd be thrilled to see it. As to whether they want to, I don't know. And that's also fine.

When was the last time you had any uh collaboration with them? What what what was the story behind that?

Uh well, I mean, I I met them years ago and I was an intern at Chicago City Limits. Uh this is the in it was about the year it was in the years right before uh Upright Citizens Brigade came into New York probably 1996 1997 and they just made improv in New York City their own

before they came in and did that. Chicago City Limits, I feel like, and yes, I was new in New York, but um Chicago City Limits was pretty much the the cool improv spot at that point,

and people were still doing a lot of short form improv, a lot of improv games, which when UCB came in with the Herald and kind of said,

"We're not going to ask you, you know, we don't we're going to do improv and we're going to make things up and you're going to know that we made it up because we said so. We don't need to, you know, get, you know, get get a there was when you do improv games, a lot of it is, you know, you're asking for suggestions constantly. And part of that is based on the idea that you're doing a magic trick for the audience. Oh, they just got this suggestion and I saw it happen. And what the Herald really said is, give us three and we're going to do 25 minutes. And you know, like this isn't, you know, we're not doing a m we're doing a magic trick in that we are doing improv, but you're going to have to believe us that this is really not,

you know, we didn't sneak in here with a script,

right? and and do you know so there there was a a sense from you know the Herald and the long form improv that UCB brought to New York at least in my experience that made

the improv games of like

I mean they did stuff like they'd improvise a blues song you know and it would be like

you know and I think today it's a little corny but it still was

pretty difficult to do you know I mean improvised songs and improvised music um absolutely

but yeah no but I met the Stangles was working at Chicago City Limits. I was interning and they moved from CCL was at the time at a place called Yan Hus Church in a church basement and that's when I started interning and they while the I was interning there they moved to a theater on 61st and 1st Avenue.

Yeah.

And the Stangles were on staff. I don't really know why they were I guess they must have been getting paid by, you know, David Weller or Jess Salmon or some of the Chicago city limits people. Everybody was above me. I was the intern. Everybody was above me. I don't know what their exact role was. They but they taught classes and I when I was an intern, I took tons of classes at night, improv classes, sketch classes. I took sketch classes from uh the Stangles and

they were great. and they ran a sketch show called uh Uncle Zeno's Chuckle Patch and uh which everybody who yeah whenever I hear they like if you talk to the Stangles about it they get embarrassed about it but I I didn't I mean you know whatever it was a sketch show with a funny name um and I think if I'm not mistaken I think Justin had a radio show maybe in Australia where maybe he was Uncle Zeno or something like that there was something like that so it was related to something that he had done in his career in the past

that was of the Zeno the word.

Yeah. I mean, you know, Uncle Xeno's struckle patch. And also, I mean, I I I don't know. I don't I don't think it was meant to be taken literally. I think it was a tongue-in-cheek kind of a kind of a name. Um, but they said to me, um, just through through doing sketch classes and improv classes and working with them, renovating the theater and hanging around with them every day, they were like, "Hey, if you want to come help out on Uncle Zena's Chuckle Patch, we need, you know, effectively someone to, you know, change the sets and be on set." And so I jumped at the chance. And that the cast was amazing. I mean, this was like Andy Daly was was in that in that cast. uh Chris Rean who went on to write for the Daily Show and Family Guy and um there were uh Terry Tokantines was in it. I think Duca was in it too I think. Um

and um it was this was also kind of an era where it it was eyeopening for me to see well-written sketches. Doug Ables was a I don't know if you know that guy. He was uh I think he might be writing for

uh Fallon now. I'm not sure but he was on Update for years. ables and and you know you want you want to hear a classic 90s sketch if I'm if I'm maybe I'm getting this wrong but I feel like Doug Ables wrote a sketch about this is this could not be more 1990s it was uh Stephen Hawking appearing as a as a contestant on American Gladiators

um you know um and it was funny I need to add I need to add it was very funny um but there was it it was

for someone coming into New New York City and really my knowledge of Sketch was mostly SNL reruns, you know, uh, Kids in the Hall were great, but they also were so indie that there was like a step removed from

Y,

you know, well-written stuff. Um, and and I really I was just unaccustomed to great sketches being performed live um, not on TV. And it was it was astonishing to me

that all these people weren't famous immediately,

you know, like it just was it was like um you know uh you know and that was a lot of my experience with Chicago City Limits too is I just saw all of this great comedic work and all these really funny people. Um

were you in at this time to Weekend Update and all of that? Like was that happening? Was that a result of Was that a result of of being there? Uh I was doing um uh the improv classes uh at CCL and working during the day, but then I was also doing standup at night. So I was out doing standup. The the the SNL came for me that started and the timeline's getting a little fuzzy, but um

yeah. Yeah.

Uh I was performing at a place called the Monkeykey's Paw that was MCEd by uh a guy named Randy Kredico who was

a wonderful lunatic. Um, and he knew everybody from back in the day and you know like Soupie Sales would come on the show. Um, and Colin Col Colin Quinn would come by and and do sets on the on at the Monkeykey's Paw and you know I was a guy who was a pretty sharp little writer and I didn't have too many objections to I think I at one point Colin was doing a bit and and I had come up to him afterwards and I was like hey this joke is funny but you could try this and he was like that's funny. And when Norm McDonald got fired from Weekend Update, Colin slid into that role and Colin rolled through the Monkeykey's paw one day and he had a handful of little pieces of paper and he was like, "Here, facts, jokes, here, facts, jokes, here, facts, jokes." And everybody who had been working at the monkeys paw on Kredico's show, you know, got to do it. And so we would basically the monkeykey's paw was I think it's called Kettle of Fish now. It's right next to the duplex in the village. you had to step down into it. And so we would, you know, we would uh I I MCED that show and I would bark in audience.

We'd stay out, you know, and we'd and because it was Greenwich Village on Friday and Saturday, you could sometimes bark in three or four full audiences. So you'd get in two or three sets and it was just a great

Yeah. with, you know, I mean, and he was like a a big left-wing guy, like he lived with uh uh William Consler's family.

Okay.

Uh uh and um all Oh, yeah. So, um you know, uh William Consler's daughters were uh waitresses at the Monkeykey's Paw and we would organize like all the guys. There's a ton of people from WBAI that hung out there and drank there and that was like the big left-wing uh radio station back then. Um, it was just it was just a thrilling place to be a be a part of in an era where political comedy was really cool. The Simpsons was busting out all those great

Yeah.

you know, political episodes and seasons, you know. Um, and so we would we would all send our jokes in all week and then huddle around the TV that had the captions on it and and see if we got a joke on, you know. Um, so that's when that started. I mean, that was all I can really tell you is pre 911, but yeah, I mean, this is

I was gonna say it's around the same for sure. It's it's it's within

95 to 2000. Yeah. In that era.

Um I my gosh, I uh you know, when Ben said that you and I would connect, he was he was certainly certainly right. I'm so grateful to know you. I can't wait to to see how else uh collaboration and and and whatnot can happen. Um, you know, you just I just appreciate this so much because you've been part of the bones of comedy. Um, like like again, I can I I have as you're telling these stories, there are so many vicarious feelings that I just some of the things that you're talking about are things that so many of us who are on the other side of that screen sometimes you want to just look at it from from that perspective on on the other side of that fourth wall. These are things that we wish that we could be a part of and you were a part of it. you're part of all sorts of stuff. And again, we've only really scratched the surface. Um, I do want to finish with the Billy on the Street story

because it is it is one of the it's one of the greatest and I know you've been a part of so many other things. Um but but at the end of the day um this was one of those moments where you know when Dave was about to leave or when he was moving in towards leaving he would talk about you know you'd see him how he would talk about how how Jimmy's giving away things and playing games on the show or or or on his show or or people were you know tweeting and and and the Twitter uh culture that you were talking about you know Dave would take the computer and be like all right and he would archaically type ridiculous things and it was just it was so good. Um, but during his last, I believe it was in the last couple weeks of the show, was in the last month for sure,

he got to be a part of something that was really hot at the time, that was Billy on the Street

and and and Billy Igner and and and you were there for when that segment was shot and it was one of my favorite things leading up to the end of Letterman's run on Late Show. You were there for that. I would love to hear that story as we bring us out today uh for this, you know, your first time on the Letterman podcast.

Sure. Sure. Yeah. No, I mean um I I the only reason I was lucky enough to be on that shoot and also that shoot was not a Billy on the street production. That was a that was produced by the Late Show.

Okay. Um I was going to ask.

So it was produced by the Late Show and I was the senior writer at True TV at the time.

I had written for Billy on the Street, but that was sort of uh separate. I'd written a packet for Billy on the Street and they I didn't get hired, but they bought uh one of the bits out of um out of the packet. It's uh anyway, we don't need to go into the one I did write, but the um what I what I will say is I was tremendously impressed by Billy Iikner's ability to ingest a script that was very intricate with a lot of jokes and replicate the script almost word for word. I mean, and um it was just a huge also Billy was very at the I guess when you talk about being um you know, adjacent to show business. I do have a photo and I'll see if I can find dig it up and and make it uh available to you where there is a picture of Billy and Dave on the street and you can kind of see in the background there's a couple of crew people and I'm back there like you know like you kind of have to like do a circle around it to see and I feel like that's right way. Yeah, Rich, this is this is the this is the sweet spot of this show right here. You just encapsulated what this show is. Yes.

Anyway, go ahead.

Yeah, like that's what my show that's what my showbiz career is. Showbiz is here and I'm just just over there. Just not really. You got to look for me. You got to squint a little bit. And I'm just I'm just over there. Um but I I didn't share that photo for a very long time because Billy took his um we talked about context earlier. He took context very very very seriously on that show as well he should. And he wanted that the way that show actually worked. It was like He a lot of times it's shot around the flat iron building. The reason it's shot around the Flat Iron Building is the sidewalks are very wide. So he can go down and there's there's a lot of foot traffic on those. Um and when he's walking down there, there is a trail of people behind him from uh at the beginning and there also have people in front of him that have uh the release forms. And the release forms are huge. Without the release forms, they can't do it.

So they have people with releases at the at the front and at the back. and then PAs and directors. I I might be making this up. I feel like I'm not, but I feel like I I think Bill Sheff was there um in that crew behind that. And I've just I'm just a huge Bill Sheff fan and I adored his late wife Adrien and so it was just I mean, you know, look like here's Billy Edgar and David Letterman. I mean, this is and they really felt like generational uh spiritual partners, you know, I mean, you know, and and so as a comedy fan, it was it was great to see that, but I would have been fine just to hang out with Bill Shift and look at a monitor.

Um, but was what was really interesting, I I didn't tell the story of being able to be in that crew behind for so long because it was so important to Billy that Billy on the street really looked like one guy. The whole gag is so dependent on

here's this maniac and it's a

Yep.

Well, I mean what is what it's what's great about Billy on the Street is it is a classic example of you know the you know comedy is either taking some something that's super super important and acting like it's nothing or taking something that's nothing and acting like it's super important. And what Billy on the Street does is it takes something that's super unimportant, which is celebrity trivia, you know, and making it the most important urgent, you know, and he has this

urgent. Yes, that's a great word for it. Yes.

I I mean, Billy's a big guy, too, you know, and to have him storm up at you, you know, and be like, you know, why is Madonna doing this, you know? I mean, like just that in and of itself. And if there is a big crew of people or even the perception of a big crew of people behind it or if people know and by the way big crew there's like eight people, nine people but like you know if there is even that perception then the gag is ruined and Billy got that and he was strict about it and it was like there was a little bit of he had a little bit of reputation at True TV. He went moved to True TV after a while. He had a little bit of reputation as a diva and there were some people that were not crazy about Billy because he had um I mean he was hot on the internet, you know, like like nothing really got ratings but like you know I mean Impractical Joker got ratings but like uh but you know I mean we had Amy Sedaris and you know uh great comics coming in and they they didn't really get big ratings. Um, Billy didn't get big ratings, but like the the product was there and it was like

my my attitude with with, you know, I mean, Billy was demanding for the things that he said and the things that he wanted, but from where I was coming from as a really social media person and I was trying to have the voice of True TV be funny.

For me, the product was there. He was delivering really good comedy with a really good attitude, with a real sharp sense of what he wanted to do and how he wanted to do it. And so in that situation, I feel like diva behavior is the cost of doing business. You know what I mean? Like that's worth it. If what you're going to get at the end of the day is is that then be a little demanding, you know? And nobody's throwing cell phones at people and you know what I mean? Like I mean I don't know. the show is named after. Look at the guy who the show is named after. Like I mean at the end of the day and again Dave's not a diva, but at the same time I mean there's a there is a strength there of character

where you got to hold the line because the content or the art is that important.

I got a good I got a good Dave story from the Billy on the set shoot um that I'll tell you is we're walking along and um somebody runs up to Dave, right? And and kind of is like a little close to him and he's like, "Hey, I got a joke for you." And Dave goes, "All right." You know, right? And he goes, he goes, he goes, "What's the best part of sex with a horse?" And Dave just looks at him and goes, "Well, you probably get a ride home afterwards."

And it was like he knew the joke.

Like like Big Lman knew so many jokes.

Oh yeah.

But it was like it was just like, "Of course that's the joke." You know what I mean? Like And it was just like this guy came up and you could see the guy was just like, "Uhoh." But it was just this really amazing moment of like no that you're face to face with a comedy genius and the reason he acts the way he does and the way the comedy that he puts out there is because he knows what's great and he knows what's been there and he knows what's hack and he knows

the rhythms, you know, like and so it was just it was just I it might be the happiest I've ever been as and I try not to get, you know, starruck And oh yeah, but when you're looking at Dave Letterman in the last couple weeks of the Late Show at the Ed Sullivan Theater running around 23rd Street with Billy Anker doing Billy on the street stuff and

it was it on 23rd.

Was it on 23rd?

23rd. Yeah, they they would they would it's usually starts on the it's just it's those wide sidewalks. So it would be 23rd.

I I realized for Billy on the street, but I meant what I was asking is so Dave took his crew and they basically replicated Billy on the Street where they do it at the

No, no. It was Billy's crew. It was Billy's crew.

It was Billy's crew. Okay.

It was Billy's crew and Billy's setup and Billy's producers. And I The only reason I got to do it or be there was really just because um I heard it was happening and I begged to be there. I didn't have any I didn't have any official role. I mean I I was there because I did the social media for True TV so I could and Billy as True TV talent ostensibly we you know but of course in that situation the worldwide pants people had locked down all that stuff and they wanted to control all of that social media as well they should. Um and Billy I I mean I don't know I was not in those meetings but I would assume that Billy would was

as honored and delighted that this was happening as anybody. I mean it really felt like it was a special thing. Yeah, it really did. Um, and it translated so well as for the viewer. Um, you know, you talk about that the the urgency of it and and and again, you know, Dave being part of stuff that goes on nowadays. Um, you know, hanging out with the kids as as as he would probably put it um is such a great thing because now you get this sort of fish out of water kind of a thing. Um, but he's he wasn't a fish out of water. Watching Dave run with Billy with the he had this big cheesy grin on his face. That's in my mind that's a legit grin. Um and it translated all the way. It was such a wonderful wonderful segment. It was uh what a memory that you have that you got to be a part of that. Um

if people want to find you, um obviously we can go to deathbedwriting.com and and I I highly highly recommend people will go over to that and what you and you and Ben are doing such good things in creating that. It's such a great premise

and I should I should definitely say that Kevin Maher and Dan McCoy were also huge parts of of of building it. All those guys were really instrumental just in terms of that stuff. So yeah, but

and that's that collaboration piece we were talking about earlier, right? And and and uh it's such a wonderful wonderful thing. Are you still doing dates though? like are you are you going out there doing it or are you are you

well you know the uh the the joke I like to say is uh you know I I say uh you know people ask me if I'm doing standup and I I say uh um I do stand up whenever I'm asked so no uh uh but no I I do actually it's

page though if can they book you

I uh you know I mean I I did a ton of standup last year I just I was lucky enough to get asked to do Emily Flakes show out in Brooklyn. Emily Flakes, a wonderful comedian and New Yorker cartoonist. Uh, and she just thought to invite me and I got to go out and do that. Um, which was really, really fun. Um, and, uh, I did stand up a couple of days ago. I have a I have a new, you know what always gets me back out to stand up is having a new joke. And, uh, the this is the new joke that I that that's been in the back of my head that's that's been pulling me back to the stage where I like to say um, I say uh, I'm kind of a a moderate on Trump. uh when he dies, I'll just uh you know, celebrate quietly at home. No need no need no need to go out and ring bells, make people feel bad. You know what I mean? I'll I'll celebrate. You know,

I don't I don't need

a great joke.

Um it's a great joke. It's a great joke to go out on.

Rich Duncan, you're awesome.

I appreciate you very very much. There's a couple of people I want to connect you with as well that I think uh I think will help definitely promote some of this stuff, but also um I think you'll just be again the thing that I love about this process uh is the brothers from another mother part of it and I feel like you are one for sure. Um I owe Ben another beer for uh for for introducing us and I appreciate that very very very much. Thank you so much for taking time on Oscar day. We're filming this uh on on on Oscar day. Um, thank you so and and we're gonna go watch Conan go do his thing here like right about now. Pretty pretty close. The red carpet's going on right now. And uh I just want to say thank you so much for uh taking time. You've inspired me today. You know, I love talking to people who go and they just unadulteratedly try. You know, they might have a career doing something or whatever, but then they're going and shooting after their uh their dreams. Uh whatever that looks like. And again, the process is the outcome. I think it's a very important message and and and it just it's inspiring. So, thank you so much, Rich, for taking time to come out and be on the Letterman podcast today.

Thank you so much for having me. I will take any opportunity to talk about David Letterman, and you've been a charming host, and it's been great. I would love to, uh, come back anytime, and if not, you, Ben, and I will go check out a Kings game sometime.

Oh, I like hearing that. I like hearing that. Uh, thank you so much. This has been another episode of the Letterman Podcast with Mike Chisum. Coincidentally, I am Mike Chisum. Thank you. And good night. So, here now we're going to roll the deal.

Yes. This is the video. This is uh David Letterman and I on the street.

On the street. Here we go.

Hey guys, it's Billy Iikner from Billy on the Street. I'm out here with the new host of Ease Fashion Police, David Letterman. We all know The Late Show has been a big breakout role for Dave. So, we're about to hit the streets and ask New Yorkers what Dave's next move should be. You ready, Dave?

I am.

Let's go. Miss for a dollar. Any thoughts on what David Letterman's next move should be? Uh, retire with lots of happiness.

Oh, that's very nice.

That's very sweet.

Do you realize that every step you walk, you're walking in David Letterman's shadow?

Sure. For a dollar. Should David Letterman do a podcast now?

Sure.

Okay.

What should it be about?

Whatever he wants. New York City.

New York City. Would you do a podcast, Dave?

Yeah, I I do a podcast about guys wearing shorts when it's too cold.

Oh, yeah.

Yeah. Okay. Goodbye, sir.

Good night. Thank you,

sir. What's Paul Schaer gonna do now? I I don't know what I'm talking about.

Paul Schaefer. Yeah. Well, good luck opening his mail.

Yeah, exactly.

But really, what's Paul gonna do? I mean, the Rock and Roll Hall of Fame isn't a year- round job.

Connections in Canada.

Miss for a dollar. What should David Letterman do next?

Everything.

What about like a podcast or something like that?

Yeah, you could definitely do that. Uh, probably with you, right?

I would love to do that. That would be an honor.

Um, I love you, by the way.

Oh, thank you very much. This is about David Letterman. It's not about me.

You, too. You're both amazing.

That's nice.

TWO COMEDY LEGENDS COMING THROUGH.

FOR A DOLLAR. For a dollar. What's the name of the theater? David Letterman films his TV show.

It's Tonight's show.

NO. NO. NO. THAT NEVER HAPPENED.

NO. MISS DAVID LETTERMAN. David Letterman. The man's been entertaining you for 40 years. What have you ever done?

Uh, what am I supposed to do?

It's David Letterman.

Hi. Lovely to meet you.

Lovely to meet you. You know he's leaving.

Absolutely.

He's an icon. to see you go. Isn't that great?

Thank you very much. Where are you from, ma'am?

Where you from?

Pakistan.

Oh, Pakistan. Good to see you.

Did they get the late show in Pakistan?

Yes.

That's wonderful. Remember when Drew Barammore showed her breasts?

Sir, where am I going to get my Amy Sedaris fit?

Oh, look at you with your hair. Sir, this man invented top 10 list. David Letterman.

How about that?

Yeah.

Oh, boy. He's thrilled. What's David Letterman going to do now?

That's Letterman. What's he WHAT'S LETTERMAN GONNA DO NOW? I have no idea.

Thanks. Maybe he'll play shuffleboard with Dan Rather.

Worse things.

Miss, what's Biff going to do?

WHAT?

BIFF, WHAT'S BIFF GOING TO DO?

SIR, GET OFF YOUR damn phone. He invented the top 10 list.

GET OFF THE PHONE.

YO, GET OFF THE PHONE.

DON'T.

HE INVENTED THE TOP 10 LIST.

MISS DAVID LETTERMAN.

David Letterman.

LET ME ASK YOU SOMETHING. CALM DOWN.

WHAT ARE WE GOING TO DO NOW?

EVERYONE CALM DOWN. SHOULD HE DO A PODCAST?

What's B GOING TO DO NEXT?

WHAT?

GET OUT OF HERE. I'M TALKING ABOUT THIS.

Billy on the street, ladies and gentlemen.

They don't talk to me.

Yeah.

I don't talk to them. Bang. Zoom. All right.