Inside Conan: An Important Hollywood Podcast - Allison Silverman

Episode Date: May 31, 2019

Accomplished writer Allison Silverman (Russian Doll, Unbreakable Kimmy Schmidt, The Colbert Report) joins Conan writers Mike Sweeney and Jessie Gaskell to talk about her time working at Late Night with Conan O’Brien. She also talks about having her own bathroom to privately weep in when she felt a pitch didn’t go well at The Daily Show, the reaction in the room being brutal when Stephen Colbert did the White House Correspondents’ Dinner, and her experience being in an all female writers room for Russian Doll compared to her early experiences working in a predominantly male writers room.This episode is brought to you by CLR (www.clrbrands.com), Experian Boost (www.experian.com/insideconan), and Daily Harvest (www.daily-harvest.com code: insideconan).Check out Conan Without Borders: Australia: https://teamcoco.com/australiaCheck out Conan25: The Remotes: https://conan25.teamcoco.com/Got a question for Inside Conan? Call our voicemail: [phone] and e-mail us at [e-mail] Conan videos, tour dates and more visit TeamCoco.com

And now, it's time for Inside Conan, an important Hollywood podcast. Hey. Hey. It's me, Jessie Gaskell. I'm Mike Sweeney, and welcome to Inside Conan. An important Hollywood podcast. See how we broke the title up there. Yeah, we've gotten, we're really syncing up. Talk about being in sync. Our cycles are synced. Yeah. Well, it's a different story. So this

week we are on hiatus. Right. And yet you and I are still here yes here in in los angeles oh here in the studio yeah here working recording a podcast here calling this work here on earth right but uh hiatus uh i.e our show's dark for the week yeah i.e people scatter the office is dark right um except for we actually have done some work because we're working on the travel show. Yes, we're working on a travel show and still figuring out where we're going. Yes. I think we're going to announce that in a week or two. But I'm getting all the shots you might need to go anywhere.

That's good. Yeah, I'm getting all the hepatitis. Oh, that's smart. Yeah. So A through C. Oh, I think there's even more than that now. Wow. Yeah.

I, I, I'm glad someone is hard at work trying to come up with new strains of hepatitis. Hepatidi? If you come up with a hepatitis D, then you can also do the shots for it. And that's a moneymaker. Oh, I know. That's right. Pitch it to Pfizer. Makes sense.

Good. You got your shots? Yeah. Good. And pills? You got pills? I got the pills. I got all the pills.

Again, I'm just being vague because we haven't announced it yet. So it could be birth control pills. I don't know. I don't know. I didn't want to say it when you said pills. I don't want to pry. Got to get prepped for the travel the travel week oh yeah yeah i hope we go to ohio let's just take it easy this time that is i would need birth control pills yes you would oh the men of ohio are they're irresistible uh we do have an interview

banked from our uh our delightful couple days in New York. Yes. With Alison Silverman. Alison Silverman. She was a writer in Late Night. Yeah. And she- No relation to Sarah, right?

No. Because a lot of people are related to Sarah. I mean, is that true? Well- Yeah, I don't know. She has a couple of- Who's related to Sarah Silverman? Other Silvermans.

Okay. Yeah. Right, that makes sense. But Allison is very funny. She wrote for Late Night in the 90s. Right. Well, no, actually in the aughts. In the aughts, okay.

Yes, I think like 2002 to 2005. Oh, cool. And since then, she went on to work on a lot of great shows. Yeah, her resume like name name a popular show and it's on there yeah like a popular

cool show she worked on yes she yeah critically acclaimed and also exactly award winning

publicly mainstream acclaimed it's all all the stuff other TV writers hate yes when she left Late Night

she went on to help create the Colbert Report. After that, Portlandia. After that, The Unbreakable Kimmy Schmidt. Oh, my God. And most recently, I think Russian Doll. Wow. It's crazy.

That's like, she's peaked so many times. She's good at- Nothing but peaks. She applies for, she knows what jobs to apply for. I guess so. Yeah. We should ask her for career advice. And she had a nickname for you when she worked for you.

She did. What was it? Well, it's a part of your body. Okay. Where excrement comes out. Well, yeah. Yeah. There's a sphincter in the area.

It contracts. That was her nickname. That was her nickname for you. That just shows what a cool boss I was. That she got away with calling you that. She could call me asshole. Man, I want to work for that asshole. That is very chill of you.

Because you can call them asshole. Most assholes, you have to call them that out of your shot. Right. But she did it to your face. I'm just saying there are levels of being an asshole. Most assholes, you know, you have to like call them that out of your shot Right, but she did it to your face I'm just saying there are levels of being an asshole That is one relaxed sphincter right there Yes, thank you very much, thank you You get it

Without further ado Without further ado, here's Allison Allison Silverman, thank you for being here. Thank you, Alison. Thank you. I'm excited to see you guys. Oh my God, you have a really impressive writing resume. And I mean, I just can't believe that Late Night with Conan O'Brien is on it. It's true.

Listen, you had some poor judgment early on, but then you woke up. That was your slump. They're pretty amazing four years. Yeah, so you were there four years. It was four years. Wow. And this was after you'd been working on The Daily Show? Yes.

Okay. Yeah. There were people on Conan that I'd seen. I spent time after college in Chicago when I took classes at Second City, and so I would see people like Brian Stack and John Glazer and Kevin Dorff and Brian McCann. And they were all at Conan and I just, you know, adored them. I was really excited. And did you submit a packet?

I did. Okay. And then who hired you? Mr. Mike Sweeney hired me. That's crazy. I'm sitting right here. And I don't know any of this. Yes.

Yes, you were fantastic. You were hired right away. Yeah. And I just want to know, I mean, at that point, were you the second woman writer that there had ever been? Or had there been more than that? Janine DiTullio was, back then, as it has been for most of the history, there's like some mono writers who just work on the monologue. Yes. And then sketch writers. Janine was a monologue writer. And then, yes, I think then Allison.

Ellie, right? And Ellie, of course. Oh, yeah. Yes. Ellie Barancic and then Allison. Yeah. So was Ellie there when you started? She was not. Okay. So it was all boys. It was. Yeah. It was. And when I was not. Okay. So it was all boys. It was.

Yeah. It was. And when I was at The Daily Show, it was all boys too, which is strange. It feels stranger now than it did at the time. Yeah. Because I was just used to that. That was the norm at the time. Right.

Yeah. Yeah. I'd love to hear, maybe we'll talk about your subsequent shows you've worked on and what the makeup was. How it's kind of evolved. Because I'm curious about that. It's definitely worked on and what the makeup was. How it's kind of evolved, yeah. It's definitely, I believe, been an evolution. Yeah.

Yeah, yeah, yeah. Yeah. No, there's been a lot of changes. But, you know, thank God. I had grown up just watching casts that were almost all men, if not all men, and performing in comedy groups in college that were mostly all men. Mostly male. Yeah. It's strange how things just don't seem as strange as they should.

Right. Yeah. It was all accepted. And you know what? As when we'd get submissions, it skewed incredibly heavily male. Yeah. Yeah. And I, at the time, didn't think, oh, like the idea of being proactive about diversifying the room.

It was almost like a male thing, like, I guess women don't like our show. Well, that's what David Letterman said when Tina Fey pressed him on it. He said, I assumed women didn't want to write for my show. Right. Or why would they want to write for my show? Right. And it's like, no, they did. It was just, I mean, I think one thing I'm curious about is what made you think, oh, I can be a comedy writer. I want to

be a comedy writer. Did you have people who were either mentoring you or that you admired that you thought, okay, I can model myself on them? It may be that I never really considered myself a very successful girl. I don't know what it was. Like I tend to skew like, I just feel like, I remember at one point, like someone calling me miss or something. And as they left, I thought to myself, like, how did they know I was a girl? Which is, I don't know. I mean, I'm straight. I present pretty cis. So I don't know how that really happened. But I always felt like I was just a weird girl. I mean, it's great. Today, someone wrote me an email about like a set of animators for a project that I'm hoping happens. And I looked at it and I was like, we need more women on this.

Bring it back when there are more women on this list. And that's something that I was really excited to be able to do and shocked that, well, I didn't, I guess I wasn't in the position of hiring, but that it just didn't seem like it was incredibly obvious to me at the time. Yeah. Yeah. Yeah.

I mean, I think if you spend a lot of time doing things that are mostly male, then yeah, you probably don't think that often about your gender until suddenly it becomes, oh, I have to be the temperature taker of stuff for women. So you were that on multiple staffs, it sounds like. I was. Yeah, that's true. And I do remember that, you know, I remember that coming up more at The Daily Show because we were dealing in politics. And I think I think there were moments when that felt strange to me. And I think there were also moments where I felt like, yes, I'm ready to tell you what a woman believes about this. Gather round. Right. And I remember doing one bit there called, well, I'm ready to tell you what a woman kind of believes about this. Gather round.

Right. And I remember doing one bit there called, well, Vance DeGeneres was a correspondent on the show. And DJ Javerbaum and I did, we kind of played on how skewed the show was or how skewed news was by having a piece called Women's Health with Vance DeGeneres that had like, and it was just all awkward. And he was talking and, you know, saying all kinds of things that he, his delivery made clear he didn't understand. And that was fun. Yeah. Yeah. I remember Corral was a guest host. John Stewart was actually not there. And they kind of couldn't get through rehearsal because it was just so awkward to be saying all these things to each other. I kind of loved that.

Well, yeah, and I don't mean to make it all about you as a trailblazer, but it is remarkable that you probably didn't feel that way at the time, but sort of looking back, that there were just not that many women riding in Late Night. You're on a short list i would love to know they're probably you don't have to share them but

i bet there were tons of times maybe where you felt you had to i don't know whether you felt you had to bite your tongue about stuff going on or just pitches or well i was i'm just remembering this actually which doesn't quite answer that question, which I'll get to. But I remember, because my mom has this picture of me framed that was from a magazine or something, and it said that that year we were, as we were perennially, up for an Outstanding Writing Emmy. And of all the late-night writers, which was probably like 60, I mean, they're big staffs, I was the only woman on that entire roster. Yeah. That's incredible. Yeah. Wow. So that was like 2004 or something. Yeah. Yeah. With regards to, I don't remember. I mean, I think I just kind of, sometimes I just felt like

this is just such an interesting little window. i'm not going to close anything down because i never got to hear this stuff before it was really fun so i i don't remember times where i mean that room was just very silly you know so i didn't like i didn't i don't remember times when i felt like i i was uh particularly offended or yeah right yeah because it's it's all blur to me you know no but seriously. And also, there are things now that are considered like, oh my God, that would be incredibly offensive. And so going back in that time, I don't know if it seemed that way. Right. And you don't want to kind of create wounds that weren't there already. Oh, come on. Let's do it. No, no, absolutely not. Well, what were your first impressions of working on the show when you started?

Do you remember? I remember when I came to my interview with Mike that Glazer and Andrew Weinberg, I think, were throwing around a football in the elevator bank. Oh, those two jocks. Oh, my God. Oh, boy. And I remember there being, the place truly needed to be renovated.

It was very, very disgusting. And there were the ceiling tiles. There was a ceiling tile that was out of place. And, like, there were empty cans up there in the ceiling space. Oh, yeah. You would talk about how people would try to throw things up and land them there. Yeah. This happened a few years before you came on board, but the food was still up there.

And we had a real mouse situation for a long time. Yeah, we'd eat dinner after the show. And I think Tommy Blotcha, somebody punched some tiles out in the ceiling and started throwing leftover food up there. And it became a nightly tradition for no good reason. But that's, I think, what people expect when they hear about a comedy room. Yes. They imagine this just pigsty of beanbags and Cheeto bags. It was gross.

Yeah. I'm sorry. I apologize to everyone. How was Sweeney as a boss back then? Once again, we're out of time. You can say anything. I'm going to step out. What I remember is very jovial, a lot of fun, long nights, some moments of indecision.

You bet. Well, I've come a long way since then. That's his trademark. Yeah, I know. Well, you know, it's hard to decide. It's not a precise science. It's not accounting. Up until the deadline and then two hours after that.

I would like to brag that I'm indecisive in all facets of my life. That's very decisive of you to say. Not just comedy. No, late nights. Some of them, I will say like there was great variety. One of the things that I really made me excited about being on the show was that you got to produce your pieces. So sometimes you'd be in the editing room or sometimes, I mean, there'd be amazing moments where, you know, at 10 p.m., 10.30, we would decide that we were going to do some piece and you would leave a voicemail message for Bobby Berg, who was our set designer. And the next morning you would come in and there'd be a set for something ridiculous. I've never encountered that anyplace else. You know, I haven't been everywhere. Right. But it was really

pretty amazing. And Jason Kirshner was an artist and set designer and he did amazing work. Oh, right. Right. He was great. Yeah. No, I mean that Late Night was based on the Saturday Night Live model. So where all the writers produce their own comedy, which is great. When things

go well, you can be proud of every decision you made for those who know how to make decisions not me and then but the the bad side was if obviously as you too as we all know if something doesn't go you're just like oh who can i blame yes no there's no escape but i i think also that's why sets got built so quickly because just kind of that SNL model of making things appear overnight like magic. And all the puppetry. I just remember a lot of them were very small sets that would just appear and be kind of magical because we'd be doing stuff in stop motion. Didn't you do – oh, I hope I remember correctly.

I always loved it. I think it was a satellite TV channel. It was a channel for dogs with hearing impaired dogs. Oh, yeah. I forgot about that. And so you had a Labrador retriever and you had Paw. Did you do the puppeting for that? I think I did do the puppeting.

Right, yeah, there was a little square in the lower right to interpret it for you. Oh, it was sign language? Oh, my God. The lab doing sign language. Oh, that's really funny. Oh, it was really funny. It was really stupid. I love those fake animal paws.

Fake animal paws. That's a very soft spot in my heart. It goes back to Toonses. It goes back to Toonses, which I showed my four-year-old the other day. I was showing him, oh, I was showing them a lot of Steve Martin, and I thought I was showing them the good stuff. And then I was like, oh, Toonses. And that was what went over huge.

Toonses the driving cat? Yes, the cat who could drive a car. But he was terrible. I mean, he could drive, but then he would go over a cliff. They're notoriously bad drivers. Yes. So our show also had a history of bad, absurd puppetry. Intentionally bad.

Yeah. Yeah. And you still does on occasion. Oh, definitely. But you, you, you'd come from the daily show.

So you kind of already had that anxiety of having to produce something really quickly and the, the deadline oriented writing. Yes. No, it was, there was much more anxiety at the daily Show because we would – this changed eventually. But we would do this thing where we would get a story in the morning, and then you would go off and write your version of it with all your jokes.

And then we would all sit in a room with our head writer, Ben, and John, and you would just go person to person and read your version of it. Oh, boy. And that was scary. That was scary. Terrifying. Yeah, that was really scary. So with Conan, Sweeney would have a stack of papers and would not identify and would read it out.

I read them anonymously. I love it. Which sometimes I could tell, everyone has different styles. We always try to guess. Of course, it's has different styles. We always try to guess. Of course. It's fun to guess. It's fun to guess.

But having to read your own, oh my, I would be scared every single time. It was super scary. It was super scary. Not getting relaxed. It was hard. It was hard. There were days, of course, just like you were saying with the producing, where you just felt like you were a genius.

Right. And then other days where you would. So I had, because I was the only woman there, I had my own bathroom. So I would go in the bathroom and like weep. Sometimes I would weep after one that went really badly. But, you know, also there are just definitely people who are just much better salesmen, of course, at pitching than others. I don't feel like I'm the best at that. Those are people without a soul.

Right. Their soul is empty people. How can you do that and not be freaking out? But it's so much in the selling that I think subpar ideas often get chosen if they're sold well. Right. Sometimes it means cracking up over, you know, fake cracking up over your own edge. And I just, when I see that, I can't take it. Oh, because now you know it when you see it. Oh, yes, yes, yes. Some people are masters at that, you know. So I didn't know this.

The Daily Show is the same, similar setup where you'd produce. No, that's not the case. We would, well, this is such old version of how they worked. When I was there, we would write our version of whatever stories we'd been assigned, and then that would be put together and produced by our head writer. I mean, that cuts both ways. In one way, it's like if you quibble with some of their choices, it's probably frustrating to give up your child like that to someone else. But on the other hand, it's kind of like if they screw it up, it's not my fault. Right.

Yes. I want to hear more about having your own bathroom. Yeah. Did men ever try to get in there or do they pay you to use it? We'd be crying together in the men's room. Right. So you were crying. Right. We had no idea in the men's room. Yes, right. So you were throwing me a cry. Right.

We had no, I mean, they were- Have you ever cried at work, Sweeney? I wonder how many men on our show have cried. Early on when I had the head writing job, it was a giant adjustment for me. And there were nights after the show or maybe after the act two, act three, I'd literally walk out of the studio walk to the

directly the elevator go down and just walk around 30 walk uh and stay away for 15 minutes that's the closest i came to crying yeah yeah right and then it's like i've got to go up to that fucking ninth floor again and you know because know, because you had to do, it'd be like Tuesday and you had three more shows to do. Oh, right. I've cried countless times at work. Is that true? Yeah. Really?

Yeah. I have too. I feel like I've cried in front of so many celebrities. Oh, really? Do tell. Oh, my God. That's a great. Don't hold back names.

Yeah, that's a podcast. Yeah. Crying that's a podcast. Yeah. Crying in front of celebrities. Well, I mean, just because I've gotten a chance to write with them and at some point I always end up crying, which for me like is related to, I mean, it's toned down in the past 18 years maybe. Yeah. But it always came down to like just, you know what Conan said to me at one point in his dressing room? He was like, you can't care so much because I would just get so invested in things. Right. And I do think that one of the things about being a woman around a bunch of men, I think that there is a tendency for men to freak out at tears when often what they're presenting is just a passion or release or whatever.

Right. I'm comfortable around it. It's the way that we release tension instead of violence. If it's not directed toward me, I'm totally cool with people crying. I think it's healthy. Yeah. Yeah, absolutely. Absolutely.

I always feel better after a cry. And then I'm like, all right, I'm ready to go. Put me back in. There are years I went without crying. And I felt like I was depriving myself of feeling better. Like you'd been celibate. Yeah. Yes, exactly.

My tears had dried up. That's very sad. What were we talking about? I don't know. I want to hear more about celebrities you've cried to. Oh, yes. That's it. Oh, oh. I mean, let's see. I mean, I to hear more about celebrities you've cried with. Oh, yes, that's it. Oh, oh.

I mean, let's see. I mean, just the ones that I've worked for. Oh, oh, oh. Yeah, oh, I just mean the ones I've worked for. Oh, okay. And John Hodgman. I guess we're just friends, but whenever we have lunch, I always end up crying. Is that true?

John brings out something in me. I don't know. I just feel like every time I'm like, all alright, I'm just setting myself up to cry with John Hodgman because he's a sweet guy. I think he I don't know. I don't know exactly what it is. He just makes women cry.

You know what? I think it's because he's always encouraging me to do my own thing and I've never done it. I feel like he's always encouraging me to write a book and I'm always like I've not done it yet. Do you feel like you're disappointing him? Maybe never done it. I feel like he's always encouraged me to write a book and I'm always like I've not done it yet. Do you feel like you're disappointing him? Maybe that's it. He is a great mentor for writers. He is.

He used to run a comedy column in the New York Times and my wife submitted one and he was super encouraging to her and helped her, encouraged her to rewrite it and she eventually got one published and it's the first thing fiction she ever got published. Oh, that's great.

And she's indebted to him, loves him. And he used to be in publishing years and years ago, right? Yes, yes, an editor, a book editor. Yeah, yeah, yeah. He's a great guy. He's wonderful. So when he tells you to write a book, it sounds like... Instead of crying, write the book.

Write the freaking book. What are you doing? I thought you were so powerful and successful now. You hired celebrities to sit with you while you cried. Oh, right. I just assumed that was it. So you recently worked on Russian Doll. Oh, yeah.

Which, man, I built that down fast. So I'm curious about the writer's room there. What was the makeup of the writer's room there in terms of gender since we've been talking about gender? Right. Well, it was all women. Oh, my God. It was a very small writing room and all women the whole time. I say the whole time because some people came in for a few weeks and had other projects and other people would come in. But yeah, no, that was important to Natasha and Leslie, who were the showrunners there. It's almost mind-blowing that that even can exist.

Right. No, but things are so different. Yeah, well, so how do you compare? I know that it's probably apples and oranges in terms of the shows being so different. Yes, right. But how do you compare that atmosphere to your earlier experiences working in a crazily predominantly male writer's room? They're so, so different. I mean, all I would say is that gender did not really enter into it very much, maybe because it was all women. Like, we didn't really talk about gender all that much when natasha i mean she came in with a very clear style that she was interested in and and she immediately was like watch uh the

long goodbye by robert altman directed by robert altman with elliot gould i basically want to be elliot gould so um she right so she had she had obviously a male actor as her influence. And yeah, we just went for it that way, which was really fun to have her kind of have a sense of her being a gumshoe and just think of her in ways that were not defined by gender, of course. Right. Can I brag for you on your behalf? I was so impressed. You created the Colbert Report with Stephen Colbert, which – Oh, I didn't know that. Yes. Oh, my God.

You left Conan and you're like, oh, I'm going to – I'm working on a personal project. Yeah, right, right, right. And you created this show. I really – Yeah. I don't think there's been nothing like that. Oh, no.

Before or since. It's an nothing like that before or since. It's an all-time favorite of mine. Doing that show with him playing that character five nights a week. And there were nights I'd watch him, and it would seem like a Broadway play to me. I couldn't believe it was written that day. And the way he performed it, I could not believe how amazing it was. Thank you. Yeah. So were you working on that?

I mean, were you sort of concurrently working on that while you were still at Conan? I was not. And I should correct Mike Sweeney. I was not a creator of it, but I did come on as head writer immediately. That's pretty close. But in that capacity, certainly you had a big input into forming i think that's a brand new show i think that's absolutely true but i just want to be clear that i'm not a creator of it but um but i will take that i yeah i did i absolutely did um i was not

working on it um concurrently and you know i had seen i didn't really know Steve. Well, I'd seen Steven back at Second City, like when I was in college, back in the 90s. And then I had an office next to him at the Daily Show, but we didn't really cross paths that much. All I really remember was that he played his voicemail messages really loud. We were like in our, we were going up against our deadlines and preparing to go into the killing field that was that writer's room. Pitch meeting. Pitch meeting. Were they famous people? Was he trying to impress people with his voicemails?

They were very, very. Well, it was him and Steve Carell sharing an office. It's like really next door to me. It's crazy. But yeah, thank you. You know, I love Stephen so much. And he was just always up for anything. And it was so exhausting to write. And I remember like early on, we had this idea that David Cross was going to come on and he was going to be sort of the Al Franken to Colbert's Bill O'Reilly. He was his character named Russ Lieber, we had decided.

And we had him and we were, you know, in our office and we were pitching and pitching. And then somehow he, just as he was leaving, he discovered that the show was on every night and not every week. And he just left saying, oh, well, that's impossible. You guys, you're never going to be able to do that. And then like walked out. It was too hard, but wonderful and very, you know, it gave back because you just could feel how much fun it was. But it felt like you were the other thing was that you had to very quickly you had whatever news stories or you wanted to cover and you had to figure out okay what's my point of view

you know what's our point of view as the writers and as steven and then how do you present that in the opposite way you know kind of like parallel parking or something um or just driving in reverse so that was really it was really hard we had a great time though we felt like we were doing something special um which is a you know doesn't come around i mean it's yeah yeah it it became my favorite yeah oh thank you yeah yeah it was great and i i remember you came by and i i always think of this as kind of a big moment too when he I forget 2006 maybe I forget the year Stephen was doing the White House Correspondents Dinner right and I think you came by to say hi and you had the script or someone came by with it and and I think some of us were

really interested and we're reading it and we just were like, wow, this – I mean the jokes were fantastic. And he did it in character, I assume. Yes. He did it in character. And I think it was one of – it just got such a big reaction. Right. Because he really – you know, it was George W. Bush and – He really let him have it.

Yeah. I think so much so the next year it was like Rich Little. That's exactly right. Yeah, yeah, yeah. Doing Carson impressions. But you were there, I assume, right? So that had to be quite an experience. And the reaction, I should say, the reaction was delayed.

The reaction in the room was just death. It was brutal. Really? Yes. And I was mostly just super proud of Stephen as a performer because he kept going when it was very hard to watch because the audience, other than Lawrence Fishburne and Jeffrey Wright, who I love, who were laughing very hard. Nobody else would give anything. And the president was right there. I don't think because his performance was so, I don't think that came across when I watched it. But you were, being in the room is a whole different experience. It was so uncomfortable. It was very, very uncomfortable. I was sitting at a table with Stephen's family. And before the speech, all these celebrities, I mean, who are very strange,

but it would be like, I remember seeing Henry Kissinger talking to Morgan Fairchild. They're just the table. No, of course. But they, you know, all these people would come over and talk to Stephen's family and say how much, you know, they enjoyed the show. And then after, like, people were just keeping their distance from our table. And it was so. Oh, my God. Politics. Yeah. I went to see Stephen and I didn't even know.

I wasn't even sure what to say other than that I was really proud that he stuck to it. That's so brave. But then. Right. You look like you were having fun out there. Exactly. Right. Good for you. stuck to it. That's so brave. But then, yeah, right. You looked like you were having fun out there. Exactly, right. Good for you. You did it! You maintained eye contact with the audience?

That's it, right. And then, but then C-SPAN, people started seeing it on C-SPAN and on YouTube, which was still pretty new. And then it sort of built up afterwards that there was, and it really just felt like, oh, gosh, you know, people have really been waiting for – I mean, the amount of enthusiasm people had then just felt like, okay, people have been really waiting for someone. They've been waiting for this moment.

I remember it in my mind being really big. Right. So there was a built-in delay? There was. Like a day or was it – Yeah, something a couple of days. So it was almost – soin delay? There was. Like a day or was it? Yes, I think a couple of days. So it was almost. Yeah.

So that must have been. Yeah. It was an evolving situation. Like, are we going to get arrested? I mean, what's the worst case scenario? Right. But did you feel kind of vindicated or? Oh, it felt so great.

You know, I have to say, like, there was another before, you know, they give out these scholarships to these journalistic scholarships for high school students. And there was a cocktail party before the dinner. And I was speaking to this mom whose son was going to get a scholarship. And she was African-American. And I said, you must be, wow, your son's going to meet the president and you must be so excited. She's like, no, I'm, you know, I'm excited about this scholarship. You know, she, she was rightfully skeptical and ready to say something. So yeah, people were really ready for something like that. It was great. It was wonderful. That's a neat experience. I know. And then it seems like since then, it's really like that was maybe the dawn of what Late Night is now, which is just all.

In a way where it just, the battle lines being drawn. I mean, they were drawn earlier than that but it just got more and you know it's and where people are now playing for the larger audience of the people watching on youtube as opposed to just oh that's people in the room too right yes right but yeah that's interesting those two different audiences that you have whenever you have we went to um with colbert we went to ira We did, this was when Don't Ask, Don't Tell was still a thing. And we decided to do a- It might be a thing again. I mean, we-

Right. Yeah, right. We did a thing, you know, the whole audience were military folks. And Stephen really wanted to do a piece about Don't Ask, Don't Tell, which was, that was an amazing experience because just seeing all, you know, these troops and they were laughing at how this policy was not working and made no sense. And just, it felt important to me or cool to me that we got to show like, hey, listen, listen to all these troops is laugh at this failed policy for all the people in Congress who are saying that it would be an insult to the troops to have gay people openly serve. They're laughing at how ineffective and stupid it is. That's cool. Where were you? Were you in Baghdad? We were outside of Baghdad at this old palace of Saddam Hussein's.

Oh, right. How long were you there for? Like maybe six days or so. Oh, wow. You were there for a whole week. Yeah, yeah. Was your family freaking out? You know what? They were okay.

Did you have a satellite phone that you were checking in with? I think what happened, the one thing I know happened is that my husband put Baghdad on his weather and then like went outside in like some ridiculously like a T-shirt and shorts and it was like 60 degrees and because it was like 105 in Baghdad or something. Yeah. Right. I did a USO show right after the 2003, after Mission Accomplished. And my wife was not happy I went over there. Yeah. She's just like, oh, that seems dangerous.

But I don't know. I have to admit it was kind of thrilling on some level. Did you enjoy that experience? I guess you were just working the whole time. Oh, I mean was it was pretty fascinating right um and and just sort of you know seeing and by the way the the way that this place we were staying which was like a guest house had been an old guest house of hussein's was decorated just like trump's apartment i mean it's all the same aesthetic.

They have the same design. Guilt. A lot of gold guilt. A lot of gold guilt. I remember the guys working there, working in the dining hall, would feed cocoa puffs. There was this man-made lake that was stocked, that Hussein had stocked with fish. And they would go out and feed Cocoa Puffs to the fish. And I always, I just remember thinking that it seemed like a proper insult to Hussein to have his fish fed Cocoa Puffs.

A Western breakfast treat. Right, right. That's pretty wild. So you worked on two important in the larger cultural sense shows. And then in between, you worked on Late Night. How dare you? No, I was like, oh, this is kind of nice to get to write pieces with fake dog paws, not have to worry about politics as much. Or did you also feel like maybe were you writing

political stuff when you were at late night? I was not. I love writing stuff that's not political. I feel drained by how much political humor is out there. And I don't see as much of an alternative as I'd like. I loved the silly stuff. I always do and I don't think that it doesn't have a point of view. I think that there's importance. I don't know. Importance. I hate using the word importance in comedy. But anyway, I enjoy it.

And it's important to me because it's some of the best times I've had is watching super silly stuff. So yeah, I don't have that feeling. And I go back and forth. I mean, the reason why I really enjoyed the Colbert Report is that it was silly. It was also silly.

Yeah, it was. It was. Yes. Yeah. That's, I think, what I really responded to about it, too. It didn't feel like it was too, like I was watching a speech

that was always going to have the national anthem playing behind it. I mean, it literally did. Right, right, right. But yeah, it sort of took the piss out of that, which was great. So at Colbert Report, you were the head writer. What was the makeup of that writing staff

in terms of gender? Well, we started out with six writers. That's really small for a daily show. Well, I should say I was a writer. As head writer, I was a writer. And so was, I had a co-head writer, Rich Dahm, who's small for a TV show. Well, I should say I was a writer. As head writer, I was a writer. And so was I had a co-head writer, Rich Dom, who's wonderful. So I guess there were eight writers of which there were two, me and Laura Craft. Oh, Laura.

I love Laura. Oh, God, she's hilarious. Yeah. And I definitely found what Sweeney mentioned before, like we would get submissions and they would be 95% men submitting. We then later hired Meredith Scardino, who's hilarious and wonderful. And I've seen submissions shift a lot, too. We did have two out of eight. But, you know, I wish we'd had more.

Looking back, I wish that I'd pushed for more at that time. I felt like I was pushing. Right. I mean, that's the thing. I think when you're it's like what you were just saying about the cartoon situation. It takes a while to get to the point where you feel like you have the clout to go. Yeah. What's going on here?

Yeah. Or like, well, it's going to take two extra months, but we're going to do this work. Because it's harder to be more inclusive. It's not the easier option. Yeah. I absolutely agree. And I wish that I just sort of decided that I had that clout earlier. But again, I did push and I also didn't quite,

I was sort of in a situation that existed, you know, like I definitely see it now, you know, that it's evolved. I mean, I should have said, let's go get more submissions. That's what I think. Yeah. Yeah, but yeah, it's like you're swimming upstream and it's a very strong current. I mean –

But it has been a really – I could be wrong. People might not agree. But just you saying, you know, like Russian doll was all women. I mean that seems like a pretty dramatic evolution. Yeah. It's really dramatic. Because there's a world where a network would be like, wait, are we sure? We should get a man in there to make sure they know how to type.

Right, right. I mean. You know, where it is now, it's better than. It's so much better. No, I really think that it's been a sea change for sure, for sure. That happened somewhere in there, and I hope that I was part of it. I think I was. I think so.

And it's, yeah, the acceleration is amazing. Yeah, I mean, for me, seeing that, oh, it's a job that I'm allowed to have, that makes a big deal. Jessie, do you laugh at all the writers, the male writers, trying to be woke around? I feel like they're always trying to outwoke each other. Well, it is funny to me because I do sort of feel like liberal men are kind of the worst in a way because they always think that they are right about everything and are not really – still aren't listening though. Well, that would mean all liberal and all conservative men are terrible. Maybe all men are just bad. Well, no. And I think it's just that's who I'm around the most.

It is funny to see, because being woke is sort of trendy now, that that's people want a gold star for that. I had a friend who was part of a design group and they were looking to bring in, he's a white guy, and they're looking to bring in more people of color, more women, more diversity, clearly.

And he just felt like he was sure about the methods they should use to get those more people. And he, I couldn't sort of, he was encountering resistance because the people who are already in the group who were not white, not men felt like they should maybe have more say or might have more knowledge about how to get more of them. But he felt like he was the one who had the answer to how to recruit more people. Yeah, it was a kind of classic situation. Yeah, I don't know. It's just, I we were also like one thing that we've been discussing the last few years is that we weren't as far along as people maybe thought we were.

Like, I think there was this impression that, oh, a lot of men were thinking, well, I'm not sexist or racist. So therefore, there's not that stuff doesn't exist. All fixed. Yeah, exactly. We're in a post sexism and post racism world. Thank you. And now it can just be based on merit. But it's like, well, we weren't there. We weren't as far as we thought. Right. And so that's kind of been the acknowledging that process that has to happen.

And then it's, oh, OK, so we're not there. Therefore, now we need to maybe give like you were saying, we need to find new ways to recruit that aren't just tell your friends that we're hiring, because that's going to mean more white people or, you know. There's an opening on our show now. And I know Matt O'Brien, our head writer, got hundreds. 600. But the ratio is much higher. Way up. Oh, that's great. So that seems like a nice natural evolution without having to get out there. Yeah, yeah. Obviously, you could still do stuff like that. Right, right, right.

But maybe it's not such a drastic – Well, maybe some of us did do that. Get out of here. You've taken the blunders. Listen, I don't mean this in a pandering way, but I will say men are terrible. I just wanted to get that. Not pandering at all. When I was starting in this –

Sweeney's so uncomfortable. He's so uncomfortable. I've never been more relaxed. I grew up with women. Seriously, I love this. No, it's true. No. I know about the women who grew up with us.

Okay. Please. Oh, right. grew up with. Please. Oh, right. One in particular. Right. That's delicious. I remember, like I'm sure many listeners will do, like hundreds of articles with the headline, Are Women Funny? Oh, yeah.

There were constant Are Women Funny headlines. Christopher Hitchens wrote about it. Right. Oh, for sure. Hitchens. It was like that was it. Right. Oh, for sure. Hitchens. It was like that was. Jerry Lewis. Oh, yeah.

My go-to guy for those matters. A good 10 years worth of conversation that I feel like I'm not seeing anymore, thank God. I feel like that's been settled. What was that like? It's on the dark web now. Oh, right. In cells. Yeah. That would infuriate. Or the dark web now. Oh, right, in cells. That would infuriate. Or were you

just like, ay, ay, ay? I think that you, I think especially, well, I don't know, I'm sorry, I don't want to speak for you, but I internalize that stuff. I don't think, it doesn't, it probably makes me angry, but it also makes me think, well, I don't know, I mean, this many people wonder that,

and they're getting published. This many men can't be wrong. Yeah. So if the New York Times is publishing it, maybe they've got a point. Right. I don't know. I think a lot of times it would be used because everyone wanted to see great people like Tina and Amy and stuff. So they would be like, how do we get Tina and Amy in? Oh, we'll have it be a story of are women funny? Like, oh, thanks a lot, everyone. Why not just a great story on Tina and Amy? Right.

Yeah. You did work with Tina, right? Yeah. Yeah, on Unbreakable Kimmy Schmidt. Yes. And Ellie Kemper, who used to – Ellie Kemper. Also a Conan connection.

All these internships. I feel like there should be a documentary on late night interns because there is such, I mean, Mindy Kaling and John Krasinski and Ellie Kemper. There are many more, I believe. Did you use Ellie in sketches and stuff late night? I did not. You know, I think she, we did not overlap, I think. I did use her at Colbert Report. We hired her.

Okay. And then I worked with her at the office as well. Oh, yeah. You worked in the office. Oh, my God. Man. Name of hit show. You have the best resume.

I know. Portlandia. Oh, my God. That's right. You've got some nerve. You know, it's like, you know, no failed failed projects that no projects that didn't get to air make it on resume well i was telling sweeney earlier that you make a really good case for um for leaving a job you know like you don't want to stay somewhere too long because then you kind

of keep some momentum yeah you feel like that was intentional You don't want to end up like me. Oh, no. Well, I feel like I think about that all the time because obviously I gave up some stability because a late night job can be the closest that there is to like tenure. You know, you've got a steady income. You're going to be around hopefully. And now I have kids, you know, at the time, you know, so now I really want a steady income. You're going to be around, hopefully. And now I have kids, you know, at the time. So now I really want that steady income. But I guess I just wanted to – well, I think there's a couple things. One, I have been very, very slowly working myself up to writing a long script. It's just taking me more than 20 years.

I started at The Daily Show just writing jokes, and then I went to Conan. So it really is getting comfortable with longer forms. More than 12 pages. Yeah, because I'm so, I really, yeah, I can be very OCD about that. But I think it's also, it's been a lot of fun to get sort of the diversity of that and to feel like I'm in I'm based in New York and now I feel like okay I I know how to do episodic I know how to do late night and uh that puts me in the position to get more jobs hopefully and stuff but you know more people I mean right yeah so much about that too yeah how have you what what has been so your your process for talking yourself into taking some of these risks?

I mean, how do you look at opportunities? I think, I don't know, I guess I have somewhat of a good tolerance for it. I've been, I really kind of just look for things that seem really interesting to me. I always feel that like, I think a lot of times people underestimate what viewers will go for. I think that viewers really like you to take a strong. I don't have any sports metaphors. A strong swing. A big swing.

That's perfect. It's really great. It's right on the money. Right. I think that they appreciate big swings much more than a lot of times they get credit for. So I really am drawn to things that have a really strong point of view and places where I get the job. Yeah. I'll bring it up now.

You have a nickname for me. Oh. I don't remember the genesis of it. I think it was that you were a raving asshole. Right. No, I... And then you shortened it to just asshole. Raving asshole is long.

Yeah, for a nickname. I mean, I really love that that is your nickname for me, but I don't... Would you say that to his face? You know what? I think it probably... It's so not clever that i feel embarrassed like it's so first thought but no um i i think that i just uh maybe it was i mean obviously very ironic oh so ironic yeah um i just didn't enjoyed the idea that i could call a boss

asshole to his face and get away with it. And you were so. And no true asshole would let you. It's true. I mean, I guess it just. I was clearly used to being called that because I was like, yeah, you found out. Yeah, I think that was, I think, you know, there was things where you're like, I can't believe I, you know, I can't believe I get to have this job. Like when you would, you know, I remember doing some, Gene Wilder was on the show and we were doing something about young Frankenstein. And I had some bit where we had like 15 different people dressed up as Frankenstein. And people were asking me, some of them were

eating, some of them were like, they all had different things that they were doing. And I remember someone asking me like, how many of the Frankensteins are eating Chinese food? And you just have this like, it's just so crazy and that I could do it, that I would be allowed to do it. And it just sort of hits your neurons in a specific way. And I think it's along the lines of that. Like somehow I looked into a job where I'm allowed to call my boss asshole.

And have Frankenstein use chopsticks. Well, the highlight for me was going to your wedding. It's one of my prized possessions. You invited a boss you thought was an asshole to your wedding? Yeah. I think you two were closer. That's right. Right.

That helps. We, I see. That's right. Right. That helps. Yeah, we were just friends. And, you know, you go to the table to look for your name. And I was like, you know, I'm looking in the S's. I don't see Sweeney. And it turns out I was in the A's. It was just, there was a card that just said asshole. Oh, my God.

That's so funny. It was great. I love it. I still have it. And then was it Mrs. Asshole my God. That's so funny. It was great. I love it. I still have it. And then was it Mrs. Asshole for Cynthia? I can't remember. No, I'm sure she got it. I think we did Cynthia.

And in beautiful calligraphy. Yes. It was great. A lot of people asked me about that afterwards. Oh, right. Family members confused. Who's the asshole? Right.

I'm amazed you didn't have more than one asshole at your wedding. Because most people have more than one oh and there's one thing I was remembering I remember earlier I was saying I think I said this did I say about oh right yeah the crying and the caring too much okay this was not a crying

this is the other side of the coin I remember John McCain being on the show and he was doing secrets which I remember John McCain being on the show and he was doing Secrets, which was a wonderful bit where, yeah, someone would be interrogated, you know, behind a table and, you know, with a cigarette perhaps and the big spotlight on them and they would give up their secrets and we would write funny stuff for them. And I got to be, even though all the writers contributed to this, I got to be sort of the producer on this one with John McCain. And I spoke to him beforehand and he was, you know, we had a big list of jokes and he would check the ones that he liked and he had really good taste. And then we started shooting it and I just kept thinking

that he wasn't getting the lines just right. I kept pushing him and pushing him and we just started doing way too many takes for a sitting senator and someone coming down and advising me that I had to stop torturing the set was he cool about it oh i'm sorry to use the word torture there uh no i am um he he was going with it but it was just you know i mean you can't he's not an actor yeah but i was just like i

couldn't let it go. I just kept pushing and pushing and pushing this poor man who had agreed to give us his time. It was your apocalypse now. Glad you got that off your chest. Wow. Well, Allison, thank you so much for taking time out. Yeah, thank you. Thank you.

To sit with us. This was great. I hope your, whatever your next project is. It's going to be a giant hit. It's going to be the next biggest show that's on television. So look for that. TBD. Thanks, guys.

No pressure. Thanks, Allison. Okay. Well, that was really cool for me. I mean, I think you could tell that I was excited to meet Heather. Yes, I'm glad you guys got to meet. Woman writer. Yeah, yeah, yeah.

Oh, you too. She's amazing. You're fast friends. And I'm still asshole to her, so that's important. No, but you two have, there's a camaraderie there. Yeah, no, she's fantastic. I'm always excited to see her. Yeah.

And get called asshole. And get called asshole. You don't get enough of that at home. Well, when the kids are home, I do. We're back in the office next week. Right. And we are going to have a behind the scenes episode. That is our plan.

Where who knows what's going to happen. It's going to be a hustling bustling office again right which i'm looking forward to full of low-grade drama but we'll try to amp it up yeah we'll add some sound effects yeah it'll be impressive now behind the scenes next week so yeah so latest we'll hope to see you all. I will not see you. Oh, my God. Such an idiot. Please. Oh, God. Jesse.

Jesse. Why did I say that? You're an idiot. Those are our new names. You're an idiot. I'm asshole. Fuck. Okay.

Well, this is idiot signing off. And this is asshole until next week. We'll see you next week. We like you. Inside Conan, an important Hollywood podcast is hosted by Mike Sweeney and me, Jesse Gaskell. Produced by Kevin Bartelt.

Engineered by Will Becton. Mixed by Ryan Connor. Supervising producer is Aaron Blair. Associate producer, Jen Samples. Executive produced by Adam Sachacks and Jeff Ross, Jeff Ross, and team Coco and Colin Anderson and Chris Bannon at ear Wolf.

Thanks to Jimmy Vivino for our theme music and interstitials. You can rate and review the show on Apple podcasts. And of course, please subscribe and tell a friend to listen to inside Conan on Apple podcasts, Spotify, Stitcher, Google podcastss, or whatever platform you like best. Ta-da! This has been a Team Coco production in association with Earwolf.