From The Comic's Comic

Episode #386

Alison Leiby is a writer and comedian who started her own showcase at the Upright Citizens Brigade Theatre in New York City called It’s A Long Story. Leiby’s story is still being told. In TV, it has included late-night writing on staff for Comedy Central’s The President Show, and The Opposition with Jordan Klepper, as well as The Marvelous Mrs. Maisel. She’s written jokes for Triumph the Insult Comic Dog, published essays in McSweeney’s, Cosmo, Marie Claire and The New York Times. And her initial work punching up jokes for Broad City has led to a lengthy working relationship with Ilana Glazer. Leiby executive-produced Glazer’s Comedy Time Capsule and her Amazon Prime Video stand-up special, The Planet is Burning. Glazer now is presenting Leiby in her first Off Broadway production of Alison Leiby: Oh God, A Show About Abortion, which begins previews April 25, 2022, at the Cherry Lane Theatre in Manhattan for a limited six-week run. Leiby sat with me to talk about how her comedy and writing career evolved from late-night TV to prestige comedy to her own very personal and politically active work.

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NOTE: This would be a great week to read the transcript, because my apologies for the audio quality on this episode — my sink decided to become haunted by ghosts (or more likely, whatever my neighbors were doing with the pipes) and caused a ruckus for a few minutes. I hoped I could edit around it, but I should’ve just yelled CUT and asked Alison to bear with me as I relocated my computer and microphone. Argh. OK. Enough of me making excuses. Let’s get to the transcript!

But first, here’s Leiby from last year doing a shorter set that mentions her pandemic experience, abortion included, as part of a Comedy Central webseries presented by Ilana Glazer:

Congratulations in advance for your Cherry Lane Theatre run.

Thank you!

That’s gotta be so exciting. Not just for you personally, but just knowing as a comedy journalist/comedy fan, the run of people who’ve come through Cherry Lane in the last few years — Alex Edelman, Jacqueline Novak, Hasan Minhaj.

Yeah, like to me, when I started thinking about the show, the goal was just to get a six-week run at Cherry Lane. That to me, like, I’ve already achieved everything I’ve wanted to with the show. I mean, obviously, I hope it continues on beyond this. But it’s such a special place. And it’s so well regarded in terms of the performers that do runs there, and it’s an achievement just getting to do it.

Now, I know Oh, God, An Abortion Show is a long story. So let’s go back to “It’s a long story.”

Yes! (laughing)

Was that the first showcase you hosted in the city or had you done other things before that?

That was my show that I wanted to make. Actually, when I started doing comedy, the first thing I did was storytelling. I took a class at The PIT from Kevin Allison, and as a lifelong State fan — fan of “The State,” not the government, but the comedy show. Storytelling was something that I thought was really interesting, and then I kind of went into stand-up from that. And so to me, like the DNA of storytelling is very connected to stand-up. And I just knew so many stand-ups who were great at telling stories who didn’t ever want to waste time in their sets doing an eight-minute story, if you only have 12 minutes. So I made a show where people that are purely stand-ups, come tell a long story and work out those muscles because I found it to be such a valuable thing. Which was funny because now I feel like it’s come full circle where I’m technically doing a show that is stand-up but also a hybrid with storytelling.

What was the year that you pitched UCB and started doing It’s A Long Story?

Oof. I mean, I don’t remember. A long time because it ran for six or seven years. And I ended it a few years ago.

B.C. Before COVID.

Yes, I ended it before COVID. It was not a COVID casualty, as many shows were, unfortunately. So it was going for quite a long time. It was my first like, this is my thing in New York stand-up, like my first real baby, for lack of a better term. Where it was my name, my selecting of comics. I hosted it, and I sometimes also told stories on it. And it was really fun. I mean, I’m very grateful that UCB let me do that, and so many of the comics that came through it were like, wow, yeah, this is really fun to just stretch out and do something like this. And I’m like, yes, more comics should. Like, we know how to tell a story. We’re very good at it.

Of course, you when you started that showcase, it probably wasn’t even a thought in your head, that one day you might be able to use that to tell a story about an unwanted pregnancy.

Yeah, I mean, that hadn’t happened to me yet. So I had no idea that I would ever really experience it, let alone want to talk about it onstage. But the reason I got into storytelling to begin with was I lived in New York, I was a writer of sorts and kind of circling you know, a variety of things around the entertainment industry, but not really figuring out what I wanted to do. And I had had this near-death experience when I was 19. I had back surgery and had a severe medical complication where I almost died, and they did an experimental surgery that saved my life. And while I had processed all of that in therapy, I hadn’t processed it creatively yet. I was trying to do some different things I’ve written about it a bit and then I tried storytelling just as kind of a way where I was like, alright, I can tell more or less this story in eight or 10 minutes and find some downbeats and find some funny moments. And then once I did that, it was like, Oh, the funny moments are way more fun to talk about and I just want to do stand-up. Taking a very traumatic or — I wouldn’t consider my current show about trauma — but taking a serious event and talking about it onstage is not new to me, but I find it kind of funny that that was what I first started doing and now here I am with this huge moment. And it’s kind of the same thing.

I know you’ve also had to deal with blood clots, too, right?

Yeah, that was the experimental surgery.

So I mean, you could have a whole separate hour. Not that I’m trying to pitch you the next show already. But you could have a whole separate hour just about the American healthcare system.

Oh, yeah. I mean, you know, that story certainly deserves its own show. I certainly find it to be much more harrowing than the one I’m currently doing. So it probably takes a little bit more emotional and mental energy from me.

Right, because this story has a happy ending.

Yes, a great one. I get to do the show.

But to go back to the beginning, even before you started doing comedic storytelling in the city. What was the initial plan? You referenced circling around the industry. Were you trying to hit a bullseye somewhere? Or were you just…

I kind of didn’t know. I went to school and studied English and I desperately wanted to be an English professor. To me that was like the dream, all I could ever want, because like you just like read and write and talk all day. And now I feel like

That’s what I do.

I truly have that career but with like actual money, which, you know, academia doesn’t promise. So I really wanted to do that. And then I applied to grad schools and I got rejected from every grad school I applied to. Which I had too lofty of goals, also. Very selective you know, schools that have like six people a year get into the Ph. D. program, and I’m like, I can do that! I was 22. So then I moved to the city. I had done some freelance, some magazine writing and I worked in book publishing for a while and I worked in museums for a bit. So it was all these entertainment-adjacent things, just trying to figure out, what will be fulfilling to me? I was a lifelong comedy fan. I loved watching stand-up. I just didn’t know who got to do it. Like I thought there was somebody from NYU points to you and says, you get to do it or something. I don’t know. I didn’t really understand that just anybody could start and as long as you tried, you could kind of do it for a while. And so then when I found that world and saw it I was like, oh, this is actually the satisfying thing that I’ve been looking for. And I’m very glad that I you know, I was like 27 when I started doing comedy. 26 or 27. So I had had a couple of years of just some different things that gave me 1) some real-world perspective on the kinds of things an audience who has money to pay for tickets might be interested in. But also it makes me appreciate so much what I get to do because I’ve had jobs that I haven’t liked, and I like my job a lot now.

Once you found comedy, how did you decide then how much to focus on your own stand-up and storytelling muscles versus where you’ve gotten most of your gigs which has been for TV writing?

I mean, I think I got so many of my television writing or at least my early television writing jobs because I had been so focused on stand-up and the humor writing that can support doing stand-up sometimes. You know, lots of freelance humor pieces. But then also being out there grinding every night, and I had a day job for the first five years I did it. I was doing data entry or something that. I truly couldn’t tell you what it was now. I know I worked at USA Today briefly, but I don’t know what I did there. So I would wake up at 7:30 and go to a nine to five and leave at five and go do mics and shows until like 1am and come home and listen to sets and wake up and do it all again. So, you know, that grind I think was what got me to a point where I could get The President Show, The Opposition, and eventually into narrative television.

Is that also what first brought you in the same orbit with Ilana Glazer?

Actually it was stand-up. It was just stand-up. I had never met her, but I know we’d crossed paths once or twice through the UCB world. And we were both on a show. I didn’t talk to her at it. I just showed up and I was in the back, and then she went up and did her set and she was kind of just getting back out there into stand-up after the first two or three years of Broad City. I went up after her and after my set when I came back to where the comics were sitting she wasn’t there anymore. And then the next morning I had a DM from her that was like give me your phone number, I want to talk, and talk to you about stand-up and be friends. So it was kind of — I remember my mom when I first started doing comedy, was like, ‘You never know. Chris Rock said in an interview that they just found him. Somebody found him in a comedy club one day. They saw him do stand-up and thought he was great and look at him now.’ And I’m like Mom, that is psychotic. That is not how this works. It is never gonna be how this works. That is not even a real story, and then like it is in a way how it can work, because if you’re out there grinding and you’re getting better and you’re doing well, eventually somebody will see you doing well because you’ve spent years and years and hours.

So when Ilana slipped into your DMs, how did that feel?

I was just like, is this real? This is probably a bot. Just thinking like it had to be a joke. But it was kind of crazy. I look back on my career at this point. And I’m like, wow, it was never as bad as you thought it was. But it was at a period where I was feeling extremely overlooked by different corners of the industry. That I felt friends of mine were getting attention from. I’ve never done JFL New Faces and I never will now, because I’m not a new face. I’m an incredibly old face. But there was a period of time where that was something that was really upsetting to me. And I felt like, well, what am I doing? I’d done like one TV job at that point. What am I doing? I met on a bunch of late-night shows for writing jobs and none of them hired me. And I was about to move to L.A. — it was a month or two before. My apartment building had gone up for sale. I was renting and they were like get out, and I was like, I don’t know do I just move to LA and try and start over? I feel like I’m hitting my ceiling in the city and then in comes this DM from the comedy darling of New York at the time, being like, hey, you’re really great at this, and I want to talk to you about that, and figure out a way to work together and know you more. And even though I did move to LA for a year, I came back like every six weeks like a psychopath because I just can’t be away from New York. But it was kind of this boost of like, OK, like maybe this validation that you want is not going to come from the institutions that you expect, but it doesn’t mean you’re not successful and doing well and making something meaningful.

Did you end up moving to LA for that short-lived E! talk show?

No, I had gone out there for a few months for that. And that was my first taste of Los Angeles as a comedian. I’d been out there years before, just visiting a friend who lived there but I wasn’t doing comedy. And then I went out. I was there for two or three months for all four episodes that we got to make of that show. And then I came back and then I was here for about a year and then that’s when I moved. I did the very stupid but I guess you have to move without a plan and then like surprise, nothing worked. And the next job I got was in New York and I was like, sometimes you have to live in LA to get a job in New York.

E! had four episodes of that show was called We Have Issues, which starred Annie Lederman and Julian McCullough debating hot topics. Like The View but for young people.

Whatever was happening in pop culture at the time, which, a gun to my head, I could not answer you one single story we talked about on that show because it feels like another era.

How were you able to brush off that experience? Because at the time, it must have felt like, oh, you know, I’m going to LA. I’m working on this TV show. Everybody watches it, and then it just completely implodes.

Yeah, it was I knew at the top. Like before I even went, that it was like we’re trying out four episodes, and hoping that it gets more, so there was kind of a built-in like this is probably only going to be four episodes.

Oh, OK, they weren’t promising more than the four episodes.

Yeah. I think Michael Kosta had a four-episode show at that time. It was when they had canceled The Soup and were like, wait now what? And they tried a couple of things and then they landed on it’s just Kardashians forever now. But it was kind of nice that I knew that and it wasn’t like the devastating blow of a show getting canceled, which I’ve now experienced multiple times in the Comedy Central 11:30 p.m. slot. Specifically, that time slot is one that is just primed for absolute disappointment. Wonderful shows with great hosts that I’ve loved. But I kind of knew that wasn’t going to be the case and it was nice dipping a toe into what is the world of making TV. Of course this was incredibly low budget. E! did not want to spend a lot of money on anything. But it was a fun group of alt comics and I kind of got to see the nuts and bolts of making studio television in a way where I was not like, I didn’t like upend my life and move across the country for two months. So it wasn’t this awful devastating now what experience. But after that, I don’t think that the next job I got was for like another nine months. And that was when I went to work on Triumph (the insult comic dog), the election specials.

How did you get on Robert Smigel’s radar?

It’s got to be just that we were with the same agency when that packet went around. I did a packet. I was like packet queen for a while. I remember another just devastating era of my career where I was just, I think I did like 40 packets one year. It just felt like I was doing one every week for a different show and I got none of those jobs. But I had done a packet for Triumph and I had such a fun time writing it and it was so easy when I was doing it. I was like, oh I know this voice because I know this character, and boy is it easier to write for a puppet dog than it is for a human man. For me.

You can put the word poop in a lot more.

Yeah, it’s dirty and funny and mean, and like you can be mean in a way tha human beings on camera never get to be, and for some reason with Triumph you can. But I did this packet and Smigel loved it. And he was like, Do you mind if I use some of these jokes at the Kennedy Center? Maybe it was the Roast of James Carville or something and I was like, yeah, sure. And now looking back, I probably should have gotten paid for that in some way. But then they brought me on, and it was a completely remote job, which was great practice for now. But that was kind of my first higher-profile TV writing job, I think. Or one that people had heard of.

Right. And then you mentioned the Comedy Central slot, which were, you know, political minded, whether it’s The President Show or The Opposition with Jordan Klepper. Was that a pivot that you leaned into, for lack of a better word?

That was the landscape of non-narrative television at the time. Everything in 2015 to 2018 was like mega-political, and it was just like, well, if you want to work on a show, you’re gonna have to figure out how to write topical jokes. And that was something that like I think doing stand-up kept me very good at because you’re just trying out new stuff all the time and you generate a lot of like, kill your darlings vibes. But then also I found both of those shows, they were both just a little left of, just a straight down-the-road, The Daily Show, where it’s a sincere earnest host talking about the news. Whichever host you’re referring to. These are both characters that you got to come at things from different angles, and write kooky or weirder stuff that I think didn’t fly with an average — Seth Meyers couldn’t have said some of the jokes that we wrote for Jordan or for Anthony as Trump, just because they were in character. So you can kind of give them a pass to say wackier things. So it felt a little less dry. Now that those shows are dry, but as a writer, that can get a little tiring,

But then of course, after that, then you you get hired on Marvelous Mrs. Maisel, which is political but not topical. Because you’re jumping back to 1960.

Right, very different politics. In some ways, possibly better but in most ways worse.

But that, of course, coincides with the experience that forms the heart of Oh God,An Abortion Show. So when when that’s all happening: Do you have, do you even allow yourself to have the thought of like, oh, what would Midge Maisel do in this situation?

I think there’s definitely some influence from writing for her and just kind of you know, being able to dial in on like, what does a woman who wants to speak her mind talk about? And of course, I’m living that and have been for, you know, the last 12 years but also my entire life. So I think it did help me be in the zone to do that. Whereas I think if I were writing on a different kind of show at the time, that material might have developed differently. Just because Oh God, A Show About Abortion is not super politics heavy. It is, of course, a political show in what it’s talking about. But like, I feel like had I been in a late-night show at that time, it would have probably had more of the DNA of writing political satire or something like that.

So yeah, you were just saying working in narrative television, and period TV. It feels like every single word I’m saying has some sort of allusion or a reference to pregnancy or menstruation or…

Yes, it is wild how much the language, I found that in writing this show is like how much of like, our worlds you know, and the way we talk like, even just words that are the same but have different meanings. Women stuff is everywhere, but we never get to talk about it.

Right. Just a few minutes earlier, you were talking about learning how to kill your babies in writing?

Yes. And now I’ve done it as a person.

I know we’re talking right now before the run at Cherry Lane Theatre has even begun. But knowing that you’ve been working on the show for at least the past year, and in your head the last couple of years. As the politics keep changing, is that directly or indirectly or subtly or, how is that percolating in your head? How has the current politics in the current debate — well, there’s not a debate, there’s just whoever’s in power is making decisions. How is that influencing or somehow seeping into the show? Or do you try not to let it?

I do not address the ongoing legislative changes that are happening in this country because they are ongoing and pretty hard to pin down and write about. But also, the point of the show, is to tell, here’s the experience that I had from start to finish. It’s every detail. It’s, you know, a little bit of talking about womanhood and motherhood and how we kind of have to navigate this, and my point in doing it is to be like, this is a pretty everyday thing that can happen. And it is not a trauma. I think the more we can recognize that abortion is not just this absolute tragedy and every time it’s like this woman isn’t, she almost died because she was raped. Actually a large number of abortions that take place are people like me who are like, Oh, I really am not interested in having a baby right now, and I can go to this facility and be done with that and move on in an afternoon. If people really understood that that’s what it is. And that it’s not always like trauma porn, that maybe the power that the people who hate abortion seem to have over it can be released a little bit. I think there’s people who live in the middle of, ‘It sounds bad but also I don’t know? Women are people’ and you know, there’s a lot of people who have trouble navigating how they feel about it, because I understand that it is an incredibly prickly issue. But to present it as humane and normal feels like the most political thing I can do. There are activists who can get up and speak to statistics and stories and laws and cases or whatever. All I can do is try and make it kind of funny and approachable.

At the beginning you mentioned that if you had a vision board for the show, getting the six-week run at Cherry Lane was the thing. So are there other things on that vision board? Do you allow yourself to look past?

Yeah. I like to approach it one thing at a time. Alright, let’s get the run. And now I’m like, let’s do the run well and sell as many tickets as possible in the hopes that it gets extended. I would love to keep doing it even though now I haven’t at the time that we’re recording this, I have not done it yet, and perhaps I find it absolutely exhausting which I’m sure it will be. But I want to take this wherever it will be. People are interested in hearing this. I want to be able to this show and tell the story to as many people as want to hear it, and hopefully some who don’t, whose worldview can be unlocked a little bit by hearing something funny. You know, if it could be a special one day that’s a dream. If it’s six weeks at Cherry Lane and it ends then it’s not that different from my pregnancy.

(laughs)

But it would still be a huge, huge, huge accomplishment to just get to do a run like this and to get to do it so many times for so many people, even if it just ends in six weeks. But hopefully it goes on for a while and it’s obviously easy to point to the success stories of other people’s one-person shows that are more narrative.

Do you feel any sort of inherent pressure that you put on yourself doing the show in Texas or someplace like that? Where you want to address the elephant in the room? GOP, yes, elephant — if you want to address the elephants in the room?

A lot of puns to make. Yeah, I mean, I definitely, with going to Texas like part of me is like, I’m going because I want to run this thing a few times before it’s on its feet in New York, and I can’t really do it in New York right now. So part of me is like, stick with what you’re doing. But part of me is like I have to talk a little bit about what’s happening there. So I’m working on some jokes just for the top just to acknowledge that I’m in a place where people are getting arrested for having miscarriages and you know, I think that, what sucks is that like I don’t want people to put like the whole of abortion on me. I am just telling my story as a straight white cis rich white woman or woman in a blue state. And obviously my story is the best case scenario. But I want to be able to find ways to platform and allow other people to tell their stories that might not be as contained and jokey as mine. But that’s also not my job. My job is to just be funny with my story. Because that’s all I can really tell.

Your story, of course, is being presented by Ilana Glazer who herself in her post Broad City life. You know, she put out her own special through Amazon. She became very active politically. Using her stage. And her platform or various platforms for that. How has she been able to inspire or influence what you’re doing with her involvement?

We’ve done so many shows together and we kind of meet and chat about it. And I have, you know, a couple of different people I work with just to help me kind of get this thing you know, ready to go. But she’s such an insightful writer and performer especially when it comes to very tiny things, I think. We can all look at Broad City and see how specific and how small so many things were, that that were so funny, which is also the kind of comedian that I think I am. And this show really highlights how I like to dial in on those tiny little details and spend five minutes talking about what everybody was wearing in the waiting room, because that to me is interesting, because I like observing things and commenting on them. And I think she’s very good at that, too. So even just being around her and seeing what she latches on to is such a helpful kind of person, and then also just her political involvement is incredibly inspirational and probably part just even wanting to do the show. Seeing comedians and people get out and really embrace politics in a way that doesn’t feel awful is always an inspiration.

Well, Alison, it’s inspiring to see you be able to take this moment in your life and turn it into a show and I’m looking forward to seeing where it goes from here.

Me too.

Thank you so much.

Yeah, thank you. This was great.