Inside Late Night with Mark Malkoff - Inside Late Night: Lizz Winstead

Episode Date: October 14, 2025

Comedy writer and actor Jon Glaser is the next guest on the new season of Inside Late Night with Mark Malkoff. Lizz discusses her time as segment producer on The Jon Stewart Show and co-creating The Daily Show.Make sure to follow us on social media (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@latenightercom⁠⁠⁠) and subscribe on all podcast platforms and YouTube ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@latenightercom⁠⁠⁠ to never miss an episode!

From Late Nighter.com, it's Inside Late Night with Mark Malkoff. Hey everybody, John Schneider, back here from Late Nighter, getting you set up for what you are about to listen to, which is another great interview on Inside Late Nighter. And this time, our guest is Liz Winstead, who is a fantastic stand-up comic, who was producing the John Stewart Show. And that eventually led to the co-creation of the Daily Show. And she's going to tell Mark all about how that got started, the people that were hired at the beginning and all of the work that she did to co-produce the Daily Show, among a lot of other amazing things that she's done throughout her career. So without further ado, I send you off to Mark Malkoff and Liz Winstead. Liz Winstead, nice to see you.

Good to see you. I'm sorry. I'm going to sound like I've been screaming, which I maybe have been. You might have happened. You sound great. You know, it's interesting to me because in terms of like a, I want to say, I don't want to say it was a big break because you had been doing stand-up since December of 1983, but you're living in an apartment building. I'm guessing it's like 93-94. And your neighbor just happened to be working at the John Stewart show. And there was an open and they said, oh, would you be interested? And did you know this neighbor ahead of time? Were you doing your laundry next to them? And you're just like, oh, okay, I'm Liz. We moved in at the same time. And I think she knew me a little bit from stand-up.

And John and I had done stand together. We actually wrote a pilot together and we were friends. And so they had an opening as a segment producer on the John Stewart show, which was the show that was the precursor to many the daily show and stuff and the dirty secret was I had no idea how to type how I never learned how to type I wrote everything on longhand in fact I'm one of those people that like went out to buy a computer and ended up buying one of those like double person downfilled chairs instead, because I think I was in some kind of depression. And so my boyfriend at the time was a producer at CBS News, and he would come and meet me at the

John Stewart Show and show me how to do exactly what I needed to do on the computer. How did you get through college? Because you were doing stand-up. I know you started a car. Oh, my goodness. To write my papers. I mean, I would send my paper. And I would write them and write them and send them to stuff for someone to type them. Unbelievable. So who was in your apartment building that told you about the gig? Was it Madeline Smith? It was Madeline Smithburg.

She lived below me. Wow. That's an amazing story. And then you, of course, famously create The Daily Show together. But even crazier about this building, before we even get to the Daily Show, on the road, Jack Kerouac, wrote on the road in my building. And so in Madeline's apartment. but it didn't say that it was Madeline's apartment. She found out that it was her apartment through deep, deep diving.

But all of these Jack Kerouac fans were constantly ringing our doorbell. 454 West 20th in Chelsea was the building. And Madeline down the second floor and I lived on the third floor. So they would buzz us constantly. Can we come into our apartment and see where Jack Kerouac ran on the road? And so we were so dumb that we didn't like charge money to let people into our apartments. because since anybody didn't know, we were like, oh, I'll just say it was mine.

You could say it was yours and we'll figure it out. But yeah, isn't that wild? What a crazy story. Do you let strangers just into the apartment? That's, that's... I wanted to. We did not. We should have.

We should have charged. Wow, that's unbelievable. So you and Madeline in the same building, is this when John Stewart was on MTV or Paramount syndicated or both? It was just when the show got syndicated. So Madeline was at the show from the beginning. when it was on MTV and then when it moved to Paramount

and got syndicated that's when there was an opening for a segment producer and I took the job and then the show was unceremoniously canceled and our bosses became the heads of comedy central

and John got locked up in a two-year deal with Letterman but they wanted to do a sort of newsy show and asked Madeline and I to come board and do it and the rest is history. So you're living in the 20s and then the studio I think is on like 26th Street where you're doing the John Stewart show. Who were some of the people that you booked on the show that might have not been famous at the time that became famous or who were some

of the people that you might have stories with that you book? I would say I don't, I mean, we brought some weirdos like there was some like people from Minneapolis. Like there was this crazy polka band that I got to book to be the house on the John Stewart show when it was on MTV

and Paramount of people will remember there was a new house band every night and so we would we had this polka band on there was this cult figure called

Harvey Sid Fisher who sang songs from the Zodiac highly recommend put it in your show notes we had Harvey Sid Fisher be the house band but I mostly

we have had like, I mean, I got to segment produced George Clooney, which was really fun, and find out that he was a wild prankster in my research. And so I don't know that we discovered a lot of people. There was a lot of great musical acts who were like, you know, super good underground musical acts that were on the show. But we had heavy hitters on the show. And I think the problem with the Paramount show is that it was syndicated. And it's really hard to do a late-night show when you don't have a network, like, machine backing you. When you're in syndication, you're kind of floating around.

And the show is so funny. And the writers were so amazing. And, yeah, I can't think of anyone that we discovered, per se. But there was a ton of people who we were not short for A-list guests, for sure. Were there any Larry Sanders type moments behind the scenes that you can remember at the John Stewart show or anything just surreal or bizarre? I don't think there was really any Larry Sanders moments. There was moments that I can't believe I did.

Like, I was in a sketch. We did an NYPD Blue sketch, and if you'll remember the show for the olds who are listening, NYPD Blue constantly showed Dennis Franz's ass in the show. all the time. We saw his butt. I don't know why, but it was happening. So we did a sketch where it was me and another actor and we just were at the, we were like in a cop shop at the coffee machine wearing no pants. It was just our butts and then our police shirts. And that was the sketch. And I was like, sure, I'll do that. I was like, what am I even doing? But I don't know that there was any like Larry Sanders moments per se. I mean, I think it was funny because I think at the time,

John was actually on Larry Sanders. He was, yes. As, like, Larry Sanders being jealous of this upstart John Stewart, which was pretty funny. But, like, John didn't have, was not Larry Sanders. You know, John was very much, we were just all smoking and trying to not be self-loathing. Like, that was kind of like our whole oove of everybody, all the writers, everybody was just like, it's very self-deprecating. And, you know, the show is a lot of fun. but I don't think there was any really well not true I take it back on our final shows

we did have somebody bring a condor on to the you know like it's a condor like a pet segment and then the condor flew into the audience and started pecking at an audience member which was kind of a bummer and then we had and I can't remember who the guest was, but they were doing something and they were holding a glass at the top of their hand and they smashed the glass down and then started bleeding all over. I wish I could remember who that guest was. So we had so many mishaps. And when we got canceled by Paramount, I believe we did ransack the office pretty brutally. And I think we wrote like not great things on the walls as we Wow. So then Doug Herzeg gets to Comedy Central.

How long does it, and he comes to you and says, we want to do a show that's on Nightly and then you and Madeline develop it? Or did Doug go? Kind of. Yeah. So Madeline and I wanted to do this show about like the worst cable network in the world. And so we had come up with all these different shows like there was a show like Friends, but it was animals. that look like the people and friends, but you put peanut in their mouth and they talked.

And just like really bad. And so he was like, yeah, yeah, yeah. Let's talk about that. So they put us under this development deal to develop that show. And then once we got there, he was like, okay, I don't want to do that show at all. Here's what I want the two of you to do. I want you to develop the show that's on every day.

And I had just done two one-woman shows about the news. So this was like my wheelhouse. I'd never created a show. show like this. But the one thing that, you know, I knew was that the show, if it was a parody of the news, people were so disgusted by the media. And I knew that because I'd been on stage talking about it. And so everybody agreed, let's try and do it where if you had the sound turned down, you might not think this wasn't a new show. And then Herzog did the unheard. And unheard of where he said, I will give you a show and we're not going to do a pilot. I'm going to

give you a year to develop it on the air, which is like, I think only the Simpsons ever got that deal. So we got to make mistakes. And then I advocated for and was proven wrong instantly. They went with me. They indulged me for like, I think, I don't even know if we went to air with this idea. and we test showed it. No audience. I remember it was the first couple months. I had heard that Doug wanted to try an audience and you and Madeline were very much against it. Yeah, we wanted it to be like let the audience be smart enough to get it. And that was a flop instantly. Madeline and I were both like, oh, wow, that was a really bad idea. Let's get an audience like immediately. Because Doug apparently got, he said, you know, let's just test, do a test audience. We don't have to

I read, and that you and Madeline were instantly like, he's right. Yeah, 100%. 100%. I'm sure it helped Craig a lot doing that. And then the Kilbourne Hire was completely Herzog, correct? 100%. Okay. Yeah, yeah.

Yeah, Madeline and I got all the correspondence, and we plucked a lot of people from news, people that we knew were funny from news, news editors, people who were writing some news, some comedians who were writers, But yeah, we really needed people who could help us really execute the genre. And Brian Unger was the person who was instrumental in creating the tone and the look and the feel for the daily show correspondent and the daily show field pieces. That's what I was going to say. It's such a smart hire because he has all this experience.

And tell me if I have this right. He actually taught all the correspondence how to do. do everything from lighting the interview 100% where the camera is and and just that gravitas of being a correspondent three point lighting he gave he was yeah it was incredible uh to watch him um understand so profoundly um from producing and then being on air talent in the news i mean he had when i approached him so brian was the one who taught me how to use the computer because i was he and I dated for years and then became friends. And so the thing about it was when I went to him, he was so like just up to his eyeballs

in having to cover the OJ trial and the Menendez trial and all this other shit that he was like, what has happened to news? So when this opportunity had happened, A, he in college was Madeline's. intern at Letterman super weird um and then i became you know it connected to brian and um and i said what if would you ever leave news it's a year opportunity i don't know what's going to happen you could fuck yourself forever going back to news and he was like i don't care and it was awesome He was so good at it. At what point did you notice that you had a super fan, Chris Larson, that was showing up every taping?

Because, you know, I worked actually on a bunch of TV shows and an audience coordinator. Almost every show we would have somebody, a regular that would come. But there was the super fan, Chris Larson, and what happened? So Chris was, he's that kid. If you were a nerd in high school, Chris and his friend came to tapings all the time they were so smart

and they were kids that you just wanted to say you're going to have the best life when you are in college and you are, you're far ahead of the curve and all these jocks and all these shitheads at your school are just losers and so I know it's hard for you to understand that

but like I totally see it in you so what happened was Chris came and then Chris asked me to go to prom with him and you got stood up in 1979 it was a hockey player with a mullet and he stands you up yes stood me up so I was like I'm going to prom with Chris Larson and I'm going to wear this bombshell gown and I'm going to go to prom I'm not going to go to prom just for the show we're going to prom and I went to with to meet him. His parents were hilarious. So I go to his house and, like, his parents take me in the bathroom and they, like, gave me some shots. And they were like, you are so nice. This is so great. The parents were really funny. And then we went to dinner. We danced the whole time at the prom. Like, it was really fun. And, like, going in the bathroom with screaming girls who had booze

just taped up their legs. And, like, I was like, oh, my God. This is so classic. You're 35. He's 18. And then it was filmed and shown on the show. And then it was filmed in shown on the show. Yeah. Yeah. It was really funny. And it was just really fun for him. And he was wearing this goofy tucks. And I was just happy to be able to have Chris Larson, have a prom date, who was on TV. And, you know, I wore a red dress. We danced to Lady in Red at the prom together. And just to like give a really sweet, cool nerd. some comeuppance like some John Hughes movie

you know oh it's weird science but with me and not that Kelly LeBrock you were the same person I'm not quite Kelly LeBrock but you know it was just it was really fun it was really really fun do you know what happened to Chris

years later this is 25 27 years later or something like I think like years ago I think years ago I think we connected on Twitter, like back in the day, like 10 years ago. And I think he's like a really cool graphic designer or is doing something. But what I remember was that he totally like lived up to his whole potential. And I think he's had a great life. Yeah. I love that he, yeah, because it was a really small audience. Were there any guests that were on the show that you went backstage to say hello to

that you were fans of? I mean, there's so many iconic people that were on that show, especially early on when you have trouble getting guests and older um comedians actors i mean bill murray was like you know that was a big big get what was murray like working with him um i mean he was a great guess my my my exciting bill murray story was um while i was at comedy central i did um this wild sort of a and e biography parody called Milo Death of a Supermodel. And it was like an amalgam of all of the tragic supermodel stories rolled into one, kind of throw Nancy Spongin's life in there.

It's like the ups, the downs, the whole thing. And the night it aired, I got a call. I wasn't home. I was at a watch party. And Bill Murray got my number somehow and left a message on my answer machine and said, I spelled my name with two Zs. And he goes, Liz Winstead, you are very funny. And then that was it.

It was like, oh, my God. No phone number or anything. Matt, call me back. Just like, this is Bill Murray. You are very funny. And I was like, oh, my God, floored. It was so interesting when you launched the Daily Show in 96 because you only have CNN. But then really quickly, it's MSNBC, July.

And then I believe Fox News is October. October. The timing was unbelievable. It was unbelievable. And it really was, you know, when we launched the show, it was really sort of, there was like a Jillian news magazines on television at that point, you know, and they were just struggling for stories. So it would be like, your mattress, what you don't know might kill you, you know. And there was that and local news. And so when we launched, it was really looking at like evening news.

news magazines, and that. And then once the cable explosion happened, you know, we followed the trends of the news and then mocked them. And so, you know, things shifted dramatically on how it went. And so it was really almost made the job easier just to see how low cable could go. and they certainly did with the trial of the century of the moment and all the other garbage they covered instead of actual news and we just like were there following it.

You said when you were developing the show, there were two different camps. One, one at pop culture, the other focus on politics. So it was kind of a little, when you were there, it was a little bit of both. And then John Stewart, of course, took over and went more politics. How hard was that? I know that you wanted more politics, but was that that pressure on the network? Was that a hard thing? They were the ones that wanted more the pop culture. They wanted more pop culture and it was always a fight and I was always pushing back and I'm sure they

didn't find me at all fun to work with. But I kept saying if we're going to shit on pop culture constantly, you're not going to get guests and no one's going to remember that because pop culture isn't changing our world. You know, the information that the reason that this show made sense to me was that the people who are supposed to be keeping us informed were choosing to do lascivious stories about celebrity and that, or just like, if it bleeds, it leads chaos. And holding them accountable in a way is more fun. And then, you know, then lighten it up with celebrities who do movies and have them on and maybe have them even comment on the state of our media. And, you know, it was a very much push-me-pull-you kind of thing.

I give you credit. At one point, was the network, I had been told by somebody that the network was considering to fire you. And there were staff members that signed a petition in your defense saying that if this does happen, we're out of here. Did that happen? Yeah, that happened. Yeah, that happened. And I was utterly surprised by the whole thing. And, you know, God bless the staff. You know, it was like, it's one of those things where I always would say to them, look, I can't promise that we're going to get every joke we love on the air, but I promise you I will fight for the jokes that we think are good. And, like, having a boss that at least will try to fight for that and not just back down, I think they really liked that. And I think that the writers were definitely in a camp where, you know, they wanted to skewer the true, you know, the true, you know, the true, you know, crapping on celebrities or, you know, especially if a celebrity is like a big drunk or has a thing or a public, whatever.

just that just wasn't ever kind of my jam and so I was like didn't you bring me in to kind of like do this thing that I do and it turns out

yeah and then you know Craig wanted more pop culture I think that was his jam and I think that was a wildly known you know budding of heads and so

I'm glad that when John finally took over that the show went in a direction that it was meant to be in. Other than Craig Kilbourne pushing for the pop culture, it must have been, I'm guessing, it could be off, a dream for a comedy writer to have a host that was so indifferent and just would do whatever you told them, whereas traditionally those hosts are so opinionated

that they were reject so much, and it's like sometimes for people to get stuff on is very hard, but this was like you could do whatever you want. Was that that was a gift, I'm guessing? Did you feel that way? Yeah, on some level it was great because it was, you know, it was, you know, Craig looked like every handsome local news anchor, right? So he's like, fit the bill.

And so in writing satirically for that person, people were often be like, is he in on it or is he not in on it? And I felt like that was part of the magic of Craig as the host. And so the show, you know, in those first couple of years, was very much more how the Colbert rapport was, you know, with everybody was a character. And so when Craig left and John took over, and I think this was a good move, John became sort of the voice of the audience and then the correspondence remained the clowns so that he could be like, wait, that can't be right. You know, he could say what you were thinking as the viewer, which I think really elevated the tone of the show.

Who at the best out of all the anchors, maybe Unger, since he had the experience, but who had the best audition that you remember, or one or two of the people that were correspondents that you hired? You know, Unger didn't even audition. It makes sense because, I mean, he had the chops and he could do it. Wow, okay. Yeah. You know, when I think about who audition, you know, it's like, I think we went and saw people doing other work. And then, you know, we knew Lewis Black was going to be the Andy Rooney. So that didn't need to be an audition.

It was like, you already are Andy Rooney. just do you in three minutes about a topic. So that was that, right? Beth Littlford, we saw her doing literally a one-woman show about how to enjoy anal sex. And she had this great look of a fresh-faced celebrity reporter. That was so good. I'm sorry to interrupt. Beth was criminally underrated and I think one of the best to do it. It was so good, especially in those Barbara Walters type of, you know, that's the way to play up celebrity, you know, have celebrities on and have them in on it and playing up to all the tropes of the celebrity biography. Beth was brilliant at it. She did it really well. And I remember David, the late David Cassidy, not getting it and actually

being kind of upset. And on air said, if you ask that again, she was asking about something that he was known for. And I don't know, something sexual. And he's like, you know, you ask that again, I'm leaving. And he wasn't kidding. And it was like, she had no idea that that was going to happen. Right. Right. Yeah. So, you know, and Whitney was always so dry that Brian and Whitney shared an office, which was the best thing and the worst thing to happen, those two together. Why? A. Whitney Brown, SNL. Why with Whitney? Why did him and Unger clash? Oh, they didn't clash. Oh. They were co-conspirators of the craziest order. Like, look out. The two of them would scheme up shit that was so wild that you just look out yeah so i think brian really guided whitney and got

him to a place to um learn how to have those fake broadcaster chops um yeah and then the two of them together were just trouble on ice in a funny way from what i've told from people that worked with him one of the smartest guys but seems a little self-destructive certainly at s&L with um drugs and then um do you do you think that that's fair to say a self-destructive guy. I mean, I would say that Whitney just, I don't even know how to describe Whitney.

Self-destructive means that you would you land in the gutter. And Whitney just made decisions and then if it didn't go his way, he would just pivot. You know, right now

he's like, I saw him about four years ago. He's living in Austin, Texas, married to a wonderful woman, like doing some farming. She's a musician named Carolyn Wonderland. She's an incredible blues musician. And he's just living his best life. So I feel like Whitney is the kind of person who has so many, like, proclivities, interests, whatever,

that, like, I think he likes to get in trouble. And I don't think that he cares where that trouble takes. him because I think he thinks it's fun because he also can just land someplace else and be really happy. And I think that that's who Whitney is. If you don't want to answer this, you don't have to, but I was told that you brought Whitney to Air America and he needed a gig. He tried to fire you. Is that true to get you fired? Whitney? Yeah. I've heard that rumor also. Okay. But I haven't confirmed it. Okay. You never know. I was, I was just like, okay, talk about loyalty. that's true. If that's true, I'm saying. Yeah, yeah. I mean, I think, yeah, I think, you know,

Air America was its own ball of whack. I can't imagine because the, the individual who started it basically told you they had all this money and it wasn't true. And that was the big thing that sank it. Correct? Yeah. Basically, well, it didn't sink it. It, it was the first, because it went on for like four years after the huge scandal. There's a whole document. documentary that you can watch about it. But yeah, this guy, Evan Cohen, said that he had money, didn't have money. All of a sudden, the affiliates weren't getting paid. Our health insurance wasn't being covered. We weren't getting paid. Several people were paying. I was paying my own staff with my money. And yeah. So you're writing checks out to Rachel Maddow?

Not to Rachel. She was getting paid, but lower staff was not getting paid. And so we were, it was wild. I can't believe. And then they had new people come in that salvaged it for a while. But, I mean, I got fired. Mark Marin got fired. I'll never forget.

I was there. And it was, I don't know, three years in or something. And this new guy took over named Danny Goldberg. and he sent one of his lieutenants in to tell me that I was fired, almost all of the writers were fired, and then Marin was fired like three months later, because, get this, humor wasn't an effective tool for social change. My God. And my show was replaced with Jerry Springer, and Rachel Maddow was moved to 5 a.m. and my other co-host Chuck D

was moved to the weekends so that Jerry Springer could be one of the marquee talk show hosts on Air American. Former mayor of Cincinnati I don't, the decisions on that. It's unbelievable. I have to see that documentary. Hank Gallo gave you attribution when you were talking about

Butros Boutros Ghali talking to Craig Kilbourne. Can you tell the story about how he, Craig just didn't was like, no, this is wrong in the script. guy's name is repeated twice. Butros, Boutros, Ghali. I'm what you said if you remember. Yes. So there was a journalist in the room, and we were had the, I never wanted press in the joke reads. It was like my thing. It's like no media in the joke reads. It's a bad

idea. Like, you just don't want, you just don't want to expose anybody to that. So, journalist in there. Craig's reading the script. He stops, and he goes, there's an error in the script. It says, Boutros, Boutros, golly, why do we have to say Boutros twice? And then I said, for the same reason you say Surn twice, thinking, and then he stared at me, and I said, Duran? And he goes, oh, okay. And I was like, oh, my God. He literally was not reading the newspaper.

I mean, he wasn't following what was going other than the sports section. I mean, and pop culture. But like, yeah, it was just one of those things where it's like, oh, gosh, don't come sliding in here with massive indignance. It's always a bummer. I have to say, in terms of getting over with the audience, he really crushed it. In terms of the audience response in the studio, the laughs and that the five question thing, it really, I mean, I think people forget sometimes because he's been gone for a while, how hard he was crushing it, at least for Letterman for them to bring him in at 1230. Yeah, yeah. I mean, he definitely had it, you know, if you were going to keep with the daily show remaining satire throughout, the dude was. was really good at, he could read Promptor, even if he did, like, he's a savant at reading

prompter. And he could tell timing, even if he didn't quite understand what the, what he was reading. It was incredible. And like, I remember Hank Allo wrote a joke when Mike Myers was on for Kilburn, which was a perfect Kilbourne joke, which is one of the five questions for Mike Myers, Canada. What went wrong? Yeah. That's, I mean, so kill. born and it's just the audience like to be to have that character but I guess maybe that was partly Craig

is a person I don't know was he kind of like the same type person on very much yeah you know he was very much he was very much like he's Minnesota sarcastic

like he's from Minnesota yeah yeah you're both from Minnesota yeah and so So, I mean, he had that sarcastic thing down, and that was his humor ticket for sure. I know that you're asked about this sometimes with The Daily Show with there weren't women writers, but I mean, you said, you've said 40% of the staff were women. And when you got your first 150 submissions, and I think Madeline said the same thing. It was like two women. Yes.

Two or three. And you cover the names up, at least back then, however. when they would cover up names and just go with whoever yeah who had the best packages yeah and so um yeah and so that was like uh you know it's and since that time you know it's changed a lot it was also one of those things where in the scope of the kind of comedy that everybody was writing and submitting for, there was so few shows doing, and there was no shows doing straight up political humor. And so a lot of people weren't, forget about women, no, hardly anyone was honing their skills at writing political packets at the time. People were writing sitcom packets, late night

packets. And this was not a late night packet show. It was a whole different thing, right? and so if you can even think about like comics back in the day who were women who were doing political material like straight up it was me and like then there was like Kate Clinton and there was you know some other comics who didn't submit you know Stephanie Miller I mean maybe Stephanie Miller wasn't even doing stand up back then I don't think. wasn't doing stand-up. She had a late-night show, short-lived, late-night show at one. Was it back in the 90s then? Yeah, yeah, yeah. Tom Hurtt was a writer, and I know you worked with Tom at the John Stewart show. Yeah, so, yeah, so, you know, didn't come through, didn't submit. Yeah, but there weren't many, so it makes, that does make. So, you know, it was just a weird genre where people were like, I'm not sure if this is my thing. Also, it's a new show, so I don't, you know, it was just like,

it was very bizarre. And, you know, I just, always been really a political person and tried to mash those things together and never thought that my first big opportunity in television would be my dream show, which is a curse and a blessing, I guess. Because you don't know what you're doing, so you make mistakes and you get mad about things and people aren't caring enough. And, you know, I'm glad that they gave you a year. I mean, people forget Colbert when we're recording this just won the Emmy yesterday. But that first year he got with the press and the comments from the from america where like this is the biggest mistake he's going to get canceled he's in third place and it's just like that first year for most

people unless you know letterman had guest hosted for carson like a hundred sometimes and had the morning show failing at all this experience so february of 82 when he gets the gig he's polished and ready to go but like for most people do you need that year to figure that thing out well it's true and you know, especially when Stephen had come from this character. Sure. And like, you know, the world didn't know how brilliant he was. No idea. How funny he was as him, you know, because he had introduced himself to the world in character,

throughout, not just Daily Show, throughout all of his great stuff, right? Sure. Is it true that you and Madeline don't get residuals for The Daily Show? It is true. That's unbelievable because they are your name in the credits and stuff I can't believe that

Yeah, it was a non-union show I'm so sorry I can't believe that yet That's unbelievable What was it like doing an evening at the improv With Phyllis Diller when she was the host Oh my gosh That was, you know

That show was always a crapshoot right So it was like you could get a guest You could get a host who was Semi famous maybe another comic, maybe whatever. And so you never knew. And so when I got Phyllis Diller, I was like, oh, my God. I mean, what an icon.

And to be able to also, for the youngsters who don't know Phyllis Diller, her laugh was so iconic. And to be on stage telling your joke, and having Phyllis Diller laughing at all of them. Like, that was one of the greatest things ever. I love to hear that. I know Ben Vareen also was one of the hosts when you were at evening. Yes.

Ben Vareen. Yeah, yeah. I mean, I wish I would have had more. I'm a huge musical nerd. Yeah. And I didn't come into Bob Fosse until I was a little bit, until after that. and later. And maybe it was a blessing because I think I would have been stopped dead in my tracks if I would have the admiration that I have for Benvereign now, then I think I wouldn't

have been able to do my act. Wow. Yeah, different place. You also, you mentioned Phyllis Diller loving your material. You opened up for Roseanne. Same thing. She heard your set and she thought you were hilarious. What was that like? So that was wild. So the Roseanne story was interesting because I was still, Minneapolis is where I started comedy. And a lot of people don't know that Minneapolis is such an incredible, back in the 80s, an incredible hub of comedy. And so there was like six rooms and national headliners would come through and work at a club for, you know, four nights, five nights. And if you got to open for them, you got to know them more and more. And so you could really create relationships and develop your material totally under the radar of having to go

to L.A. and then bombing in front of like an agent and then having your whole career be screwed. Right. So Roseanne was still living in Denver. And so she would come through four times a year and headline in Minneapolis. And so we became friends. And I opened for her. and now she turned into a massively horrible individual and I it was like what is wrong with you

and I haven't talked to her for years ever since she came out against trans people and became Trumpy and like I don't know what the hell happened but she was like one of the greatest comedians of our time at the time when she debuted on Carson and got her sitcom and yeah longevity at the time

you did say the Daily Show, I know that you mentioned in an interview about John Stewart when he interviewed Henry Kissinger going easy on him. You did, and I give you a lot of credit. You had John on your radio show on Air American. You basically said your words, he's a war criminal. And what did John say when you kind of gently and politely? I don't remember. I remember talking to him about it, but I don't remember what he said. I think he said something like Liz, I'm just not you. I don't think he really didn't get into it, I don't think.

Yeah, I don't think we got into it, no. But yeah, I remember being like, wow. But I think, I mean, that was so early on. That was like 2004. And when you look at John now, and I don't think. think he's fearless now. I think he understands, yeah, I think he understands that like if you're, there's no reason to sit in a chair and talk to someone, um,

who is full of shit or horrible. Um, and not hold them accountable. Because then the point becomes, why am I sitting across from this person? If I know that they have things to answer for and I know that I am skilled to hold their feet to the fire, I should do that. Otherwise, I'm just platforming them

and normalizing the shit that they influence people with every day. And I think that, like, there's been clips of John interviewing gun people and, like, congress or i don't even congresspeople i think are state senators um he goes after them i mean he'll rip them apart i mean to sit down with that guy and force them to yes and i'm super appreciative of that yeah it was very public when you left the daily show in january of 1998 Craig kilborn was in esquire and said some awful stuff and mentioned your name looking back do you have any regrets leaving the show i mean i don't know it was a time And, you know, I recently just did a podcast with Doug Herzog, who was my boss at the time.

He had a podcast called Basic, where he said, you know, that was, you know, that was a worst decision I ever made was letting you go. And I was like, you know what? Today he would have been fired. He would have been fired today. He was suspended for one week without pay, they said, in the news. It was 1996. And watching the environment unfold. one of the things that I knew to be true was that I would not have been able to operate

professionally for my staff with knowing that somebody said those things about me publicly. And so I don't regret leaving because I don't think I would have added to positivity to that environment. Did he ever apologize, a Kilbourne ever apologized to you? I mean, I think he had to. I mean, yeah, he had to, but it wasn't. No, I, I, I, you know, in a way that I felt like, let's put this behind us and move on. No. Okay. Did you, in terms of, um, when John Stewart took over, did you have any other people that you thought would have been a good host, um, other than John if John didn't get the gig? I know a bunch of people auditioned. I didn't know, you, had any

I mean Brian Unger yeah he's very funny I have Brian Unger um he did some

yeah um I think if one of the people that Madeline and I loved when we were

initially hiring was Mike Row oh yeah he was really funny and we were hoping that he he would have been

the host but then Doug won at Craig I mean I felt I think John would have been our first

choice hands down heading up and tied up at Letterman and it would be interesting to see what that show would have been like from the jump had John been the host because we wouldn't have needed to have a satirical host. I think John would have been in much more of a leadership role in a creative role because that's how his brain works. Very hands on as opposed to Craig, which is just give me the prompter and bring him in. I'll read it. Definitely. Yeah. And so not really. You know, it's kind of like, yeah, John for the win. You started doing stand-up in December of 83 in Minneapolis at Dudley Riggs was your, Dudley Riggs was your first gig. You didn't really start doing the political comedy until like

the Desert War, correct? I was doing like sociopolit. I would do like jokes about sexism and certainly social commentary on like women in the world and things like that. But the real crux of me really understanding, because I was always political, but like making those ties between the media and politics. was really when that first Gulf War began and knowing how lied to we were by the media and that they were just reading press releases and all of that stuff

was really something that was like, I cannot believe what a dumpster fire it is that we're being fed bullshit. And so that's when it really all started for me. Yeah. So the transition really happened to go, And which meant sort of reinventing a whole new audience, you know, like some people like, no politics. And then other people were like, who's she?

She's funny. I like politics. And so it was a long slog to develop a new audience and then nurture the people who wanted more of that social political commentary. So like 92 or one, I don't even remember when the first Gulf War at this point was 92. I thought it was, the first one was like around 90, 91. 91, I think it was 91. Yeah, it was 91. Yeah. Yeah. Um, was it a tough sell for your mother to put her on the daily show on and do the recurring bit with her. Did she just love doing it? Well, I don't, what happened was it was it was an accident because what we wanted to do was, um, we wanted to have final jeopardy on the show, but we wanted to have it, um, but we were trying to figure. out like how to do it and like of course we didn't think like they're going to tell you to stop doing it like what are you even doing and so it was like how can we do it and it was like oh jeopardy's on

early in Minnesota because it was in syndication so my mom will watch it and then she'll tell us what it is and then she could not help herself she would call up and be like um all right so the is John I don't know how to say his name it's R L L whatever and then and then she just would like always be like hilarious and she'd be like

by the way give your sister a call she feels like her ovaries there's about to blow up and then she'd go bye and so the people that would the researchers who would have to transcribe it would always play it for us and we'd be laughing

so we were like what if we just have run that and do it. And so we did it for a couple of times. Then, of course, we got the cease and desist from Jeopardy. Then we got my dad into the act who would threaten Alex Trebek. And we would just have, we came up with a new name for it called Trivial Compromise. And then she would just find questions. And then my dad would give a preface on everyone to say,

Trebek, I'm coming for you. It's really funny with my wife, Ginny. Here's the final compromise or whatever it was. and then she would read it. In terms of when you were doing the clubs in the 80, when you were doing New York clubs in the 80s or so, what was like the best stand-up, like one or two stand-ups that you remember seeing

of like people that were starting out that you were just blown away with people that were like, damn, they're going to be huge. Was there anyone that stands out? Well, I would say, I don't know if I thought they would be huge, but like my favorite Dana Gould has always been

and always probably will be one of my favorite comics of all times this podcast yeah he's he's fantastic and I know he almost got Saturday Night Live at one point and you would think that yeah I mean he's I mean he's just a brilliant writer roommates he's a dear friend he's one of he's somebody who I was always like could not wait to see yeah Maria Bamford is somebody, also a fellow Minnesotan, who I think might be the greatest

living comedian, maybe the greatest comic of all time, I'm not sure, but so great. Other comics I always really loved, are you talking about back in the day? Sure. Okay. Jake Johansson was somebody who I really just loved. Kevin Meanie, rest in peace, one of the funniest comics, like, ever. He was great on Carson. I remember his Carson. Oh, my God.

Just so funny. Yeah, there's just, those are my, like. You mentioned Dana Gold was your roommate. Wasn't Janine Garofalo a roommate of you? Yeah, Janine was one of my roommates. What was that? Brilliant. Back in the late 80s, early 90s, I think.

Yeah. You know, just like rooming around, you know. It's been a fun time. time. Yeah, it was crazy. The times, uh, yeah, Dana in San Francisco, um, and then Janine in L.A. And, um, and then I crashed with both of them when they were both living in Boston, a lot, slept on a lot of couches, um, about Dana and Janine. And, uh, yeah. Do you go back sometimes? Like, did they have you back John Stewart's final show, for example? Do they invite you back sometimes since you created the template? No, I didn't go. I was not.

asked back until Sarah Silverman guest hosted in 2023, and she had me on as her first guest. What was that like? It was wild because it was a different studio. Sure. And it was very emotional, you know, to be there and to see some of the old folks that I knew, a lot of people I didn't know.

But it was, it was very menschie of her to want to be able to, A, have me on the show, and B, have me on the show to talk about what I'm doing now, which is, you know, advocating for abortion access and using humor to do that. And so it was very cool. Yeah, I know that Sarah was very involved in everything you've done. But I'm really glad that you came full circle and got to be on the show. I mean, it's amazing. You're in Brooklyn these days, right?

L.A. is not your, you don't. No, I'm in Brooklyn. It's very cool. Liz Winston, thank you so much for talking with us. Thank you so much. Thanks for listening. Please subscribe so you never miss an episode. On Apple Podcasts, please rate it and leave a review.

Be sure to go to late-nighter.com for all your late-night TV news. And you can find my podcast at late-nighter.com forward slash podcasts. Have a wonderful week, and I'll see you next Tuesday. Tuesday.