The Three Questions with Andy Richter - Anna Konkle

Episode Date: May 5, 2026

Actress and writer Anna Konkle joins Andy Richter to discuss co-creating and starring in “PEN15,” her new memoir, unexpectedly becoming a "comedy person," and much more. The Andy Richter Call-In Show RETURNS this week! Do you want to talk to Andy live on SiriusXM’s Conan O’Brien Radio? Tell us your favorite dinner party story (about anything!) or ask a question - leave a voicemail at 855-266-2604 or fill out our Google Form at BIT.LY/CALLANDYRICHTER. Listen to "The Andy Richter Call-In Show" every Wednesday at 1pm Pacific on SiriusXM's Conan O'Brien Channel. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Hey, everybody, welcome back to the three questions. I'm the host, Andy Richter, and today I am talking to Anna Conkel. She's the co-creator and star of Penn 15 on Hulu, which earned her two primetime Emmy nominations, and it was the funniest show. I love that show so much. She also starred in The After Party, The Drop, and Murder Bot. You can see her next in The Sun Never Sets, directed by Joe Swanberg. And her memoir, the same one is out May 5th. Here's my conversation with the very funny Anna Conkle. You're from Illinois, right? I am from Illinois. My dad, who a lot of the book is about, is from Illinois. He's from Glen Ellen?

Glenn Allen, sure. Glenn Allen? Yeah. It's kind of a upper-class suburb. Yeah. It's very nice. Yeah, I'm from a little further west of that. What's the vibe?

Of where I'm from? Yeah. If you don't mind me asking. You're like, this is my podcast, bitch. No, no, it's fine. I listen. If you want to ask me the question. I would rather honestly.

Really? Well, you wrote a fucking book. I know it's there. Someone could pick it up if they want, but otherwise. Well, all right. Well, we'll get back to that. Yeah, yeah. I grew up in Yorkville, Illinois, which was at the time still pretty small and still pretty

farming. Oh, cool. I went to school with a lot of farm kids. Wow. Who were at 14 and 15 driving themselves to school because they'd been driving big giant vehicles since they were eight. What kind of farms? Most of soybean and corn. Wow. Yeah. So Midwest. Yeah, it's that's exactly it. I'm from Vermont originally. So dairy and ice cream. Yeah, yeah. And there were there was some cattle, but a lot of pig farms too, a lot of people that have pigs.

So to eat. And that was, well, sure, what else you can do with them? Ride them. I've always wanted, no, I do eat bacon and I do ride them. Non-sexual. I'll ride for bacon. Wink. But I have always wanted a pet pig. They. It's complicated. Yeah.

And my experience with them is it's a fucking nightmare. What do you mean you've had? No, no. Just like when I've been around people that have pigs, they're a noisy nightmare and they are stubborn. And you will occasionally get one that's sort of agreeable. Want a little pet? Most of the time, they're just like, I do what I want, you know.

Okay. They look cute. And for something that's so fat. For something that's at delicious, they should not be so cocky. Are they cocky? Well, yeah. The vibe to me is just like they waddle around and then they like dig in the dirt and they like roll in the dirt and they snuggle with you. You need to get you a man that does that.

Rolls in the dirt. Yeah. That's not my partner. Well, you brought it up. Yeah. Because this is always something I feel about because. Because I've never written, like, the notion of like, and it's been kind of phishing me, right, kind of a memoir kind of book.

And I just, I'm like, no. Hey, I have to wait for some people, you know. Oh, I know. You know what I mean? And, and then maybe. But even then I kind of feel like, and I'm not exactly even, I'm a, I divulge. You know, I'm on this podcast and other podcasts and I realize I'm, I can spill my guts all the time all over the place.

That's my nature as well. But interesting that that didn't equal write a memoir. Yeah. So how did it happen? How did it happen that? Someone died. My dad died. Oh, really?

So half the equation was gone to that. Yeah, that is actually what happened. I mean, essentially, like, we had had a really, really close relationship when I was a kid. He was sort of the light, I would say. It was like my best friend and was the cool dad and the funny dad. and like, yeah, he said fucked up things and was a human resource manager and lost his job a lot

because that doesn't mix. But he was also... It's so good. It's so good. I have to write a character. It's just too, like if anyone was sending the fucked up cartoons around, it was him, you know?

And yeah, it was just like very much a light in a loud, intense childhood. And then in my early adult years, our relationship like totally fell apart. And I was sort of left going like, did you change? Did I change? Did we both change? It was sort of like a normal, you know, parent falling off the pedestal at first.

And then it became like far more extreme. And there were five years of not speaking. And we sort of lucked out in the sense that when we began to repair, basically I found out very soon after that he had lung cancer. And he had had cancer many times in my life. So it wasn't that, I know. prostrate, like slow moving, but like... He contained multitudes.

Multitudes. And then it was this sort of like dense two-month period of like being his caregiver. Yeah. Wow. And the book is funny, I think. But I think a lot of, I guess I think a lot of dark stuff is, you know, is funny. But it is definitely sad too. That there, well, there is kind of an either or in terms of like, how do you deal with really sad, fucked up?

stuff and you know and I come from a family where I remember like moments of big group laughs where it should have been like what and just like in retrospect like what are you people laughing at this is terrible funny people in sad moments is like that's all I want to read and watch and whatever yeah yeah you know so for a long time my family was my bit like I didn't think comedy was a thing for me, but I would talk about, you know, our dysfunction as like, ah, isn't that funny? And then it took me a while to go like, oh, fuck, that hurts. Yeah, yeah. So I think I'm like kind of processing through both in it and sort of like reexamining through

going back to memories, like what happened there because it wasn't over the, it wasn't the ten pulls of abuse, I guess. It was like the gray areas. Right. And so that made it hard. for me to go like, these things aren't big deals. Like, why do I keep thinking about it until I got older? And then, and then, yeah, eventually it was, it made me feel lucky, I guess, that we kind of mended

things before. But I think, like, right after he passed, I had a feeling of, like, I don't know why, but this feels like I have to write this. And it took me fucking forever, but four or five years. Yeah. Well, there's no, you know, he's not going anywhere. No, he's gone. See, right there.

Thank you. There's an example of it. Right there. Yeah, exactly. I feel right at home. How do people in your life react to like, I'm going to spill my guts about my dad now? My mom, because there's a lot in there about my mother, keeps going, I'm going to move out of the universe. I'm going to move when this comes out.

But has been very supportive, which has been surprising and really. nice because she, you know, she was sort of like the enemy when I was little. Really? Yeah. But so your mom is still just like a no-go? No, she's, so she'll make that joke, but she's been like incredibly supportive. Oh, that's good. Yeah, which is really nice. So I, that was, yeah, that was a little bit of a surprise where she was like, it's your heart and you have to let it out and it's your memory of it. But I've been doing the audiobook and that's been really freaky, like doing the voices of my parents. Oh, wow.

Yeah, it's interesting. Yeah, see, all this is. Does that sound at all, though, like, okay, that sounds kind of cool, or you're like, no. No, no, absolutely. No, it does sound like. For your own life, I mean. You mean, would I do that for my own life? Yeah.

I don't. I don't. No, no, no. I'm, and I've talked about it before and I've talked about it because I, you know, dad stuff. I've talked about a lot because I haven't talked to my father in. I'm 15-ish kind of years in that sort of area and maybe a little bit more. And I'm sometimes troubled by how okay I am with it. You know, I mean, because even my ex-wife, who had no love for my mother and father

and vice versa, they were, there was a, it was a very contentious relationship that could have just been garden variety in-law shit, but everybody felt like it was an apocalyptic battle, you know, which was a lot of fun to be around. Yeah, a lot of laughs. But even she after I stopped talking to my dad would say, and she would say kind of like, I know, because the catalyst of us stopping talking was issues that he had with my ex-wife and me telling him, just she, shut up. I don't want to hear this. You're like, this is my wife and, and his inability to under, and I would tell him, ask people, ask people when you get married and, like, who ranks higher your spouse or your father? You know, like, and, and, and, and, and, and, and, and, and ask fathers,

how do you feel, do you feel that you should be first in line in front of your child's spouse? Like, you know, just like, totally basic stuff. Just basic shit. And he, and, and, and, and, and, and, and, And I think the bottom line was like, you know, how dare you take her side over me? Which is like, I'm on the side of peace. Right. Fucker. You know? Yes, I do.

You know. I do. And she used to tell me I, she's like, I know I, you know, I got problems with him. But I would feel terrible if you felt terrible if something should happen and you did. And I would think about it and I would really like do an inventory as they say and be like, no, it's okay. I'm okay. Yeah. And then I would hear things from family members that were still in contact that would make me go like, oh, okay. No, it's fine. I'm fine. Yeah, yeah, yeah. It's, yeah, there's, the reproachment is not in the cards from what I'm hearing, you know, from other people. Yeah, it's interesting. It definitely makes certain people uncomfortable when they hear you don't have, like the amount of people that were like, you should really call or, you know, the idea that not being in contact was, um,

inherently wrong was hard. Yeah. And now it's like, I don't know how you feel about this, but I'm kind of live under a rock, but like seeing the no, is it no contact being like a term, like a hashtag on social media? Oh, is it?

I think so. Yeah, like, is it called no contact? Of like kids or parents, this, like this idea of like, my mom said recently that a friend, friend of hers kind of was suffering under like no contact with her. Her kid had gone no contact. contact her adult child and that it was like a trend because it's like trending on social media. I got to make something.

But it's like a turn now. People have been deciding to take some time off forever. But also I felt so isolated when it was happening. Like I didn't know other people going through it. I felt like everybody was like, why would you do that? And I didn't have the words to explain it at the time. What was his reaction during that time? Did he?

He was very upset. I mean, a lot of it. it was like in very short hand sort of explanation of what happened that this like adoration of me, and I swear the book's funny, but it doesn't sound funny at all, that this adoration of me when I was a kid that felt, you know, against feeling almost like disliked by my mom was like home. It was like, oh, someone sees me and loves me. And then as I became an adult, I was like totally smothered, essentially and grappling with that past and the nature of that past and needing boundaries and simple shit like that, that kind of disintegrated, but I felt like I had abandoned him when it

happened. And that's sort of where I realized that I put myself in this weird position of like feeling like a parent, you know, versus feeling like the kid. And so, yeah, I've had a lot of that. You have. Yeah. It's hard to see when you grow up in it because it's just normal. It's just love for you. Just like, yeah, yeah, this is, we love each other so much. Of course I'm going to hold my mother in my arms while she sobs again. You know, and say, it's okay, like whatever. Oh, boy. But also, yeah, so he was both eventually respected it, I think, and eventually we were able to, like, talk about the real stuff, but it took a really long time.

And, but at first, it was a lot of denial of just like, hey, honey, you know, it's me. Call me back. Yeah. You know what I mean? And me just feeling like a fucking asshole because I wasn't going to call him back. And I didn't have the words to tell him why. Was there ever a letter? Was there ever a...

There ended up being a letter that after five years, for five years. Oh, after five years. Okay. There was a lot of internal letters. It was like, you know, I started therapy for the first time. I went to Al-Anon, like all this shit where, you know, I was writing letters to my dad that I wasn't sending, basically, until there was the letter that was like, all right, he can respond, however, he's going to respond. Yeah. And I'm not going to like break if he says like, no, that was all your fault, you're crazy or whatever.

Right. And so, you know, fortunately, he, he ended up, like, taking responsibility and apologizing and writing a letter back. So that was a win. That's good. Yeah. And then that was like a toe dip, you know, back into the, a very different relationship. And I was a different person also, you know. Yeah. Like, was there an incident or something that happened that he would be able to go, oh, it's because of that? Or was he just kind of bewildered?

I think he, there was an incident, but I think he was just like in denial. Yeah, he had moved to Florida and, you know, and nothing. Big strike against him right there. Jesus Christ. And our relationship was already really changing. And I, again, like I just wasn't able to express why, but I knew that like I didn't feel comfortable like I used to. And actually, so right before he moved to Florida, I had a play. in New York. Mm-hmm. And all of my friends came and I was waiting tables, this great restaurant called Prune.

Mm-hmm. Random, yeah. And a bunch of my coworkers came to, like, you know, see the play. It was really sweet. And after the play, my dad had come to, they were like, oh, great a job, blah, blah, blah, blah. They were like, you're perfect. I'm just kidding. That's not what they said.

They were like, you should be a star. Yeah, yeah. Oh, my God. You need to go to Hollywood right now. I'm just kidding. I just thought you were an amazing service person. We knew you were right away tables, which I was. No, they were like.

I was very good at that too, by the way. I actually was. No, but acting man. No, but they were like, and we met your dad. And like, he's so funny. And I was like, oh, yeah. And something in me started to kind of like shut down. I was like, where is this going?

And they were like, he tried to kiss me on the lips. And I was like, he tried to kiss one of your friends on the lip. A couple of them. They were like, oh, yeah, that's so funny. And I was like, oh, my God, what? I'm so sorry. And I, yeah, I was fucking mortified. How many?

This is, is this five years into not speaking? No, sorry. Okay. So this is before the estranged. So it's just like things are, he's changing. Or I'm like, are you changing? Was I an idiot? Like, was this always here?

Whatever. So I'm like smack dab in the middle of like, you know, trying to be an adult in New York for the first time and grow up and try to have a relationship. When that happened, I was 24. Okay, yeah. It's still pretty young. For me, yeah, I was, I was, you know. Your brain's not even formed fully.

I'm still working on it. Yeah. Yeah. And so I, yeah, I was just trying to keep my own fucking. relationship happening and grow up and pay my rent barely and all that. And then this is sort of crumbling around me, I guess, is him in my perspective and my relationship with him. And anyway, and so I proceed to have like too many drinks that night for sure. And I keep sort of looking over at him talking to people in the bar and I'm like, who are you? Like I, what if I just don't,

that's, and he's not the kind of person. I knew that I could not just say like, what the fuck? Yeah. You know, and I was so mortified by it too. What would his reaction be if you said, hey, you tried to kiss my friends on the mouth. That's fucked up. Don't do that. Yeah, I think, I mean, maybe he would have laughed it off. Yeah.

Or blamed them or, I don't know, something. Yeah. Like, it wouldn't have. And I think also the truth is that not to get too deep and heavy about it all. But like something about what they said was fucked up in the moment. on the surface, but I also sort of like strum this note in me that was much older of like being adored by him in a way that I was like, and struggling with boundaries with both of my parents in many different ways, as funny as they were and eccentric and all the good things, but that it was

like this bell ringing of like something's not right here in a deeper way that you need to look at. And so, yeah, and then I didn't really deal with it. I just sort of like pushed it down as much as I could. And then I went to visit him in Florida and his new condo. And it was, it was, and I confronted him about that there, among other things. And it did not go well. And I left. And then I didn't see him again for five years.

Yeah. This is a comedy podcast, right? Yeah, no, it's, well, it's whatever, it's whatever it is. No, I don't wear, yeah, you seem to be. worried about like it's new to be talking about like i'm i'm yeah i'm just new to be talking about this like i haven't much yeah because it it's it's not even out yeah right so yeah so this is all new i can see that yeah can't you tell my loves it's so anyway comedy you didn't set out to be funny did you no you wanted to be like did you want to be like broadway yeah yeah yeah i went to school

for musical theater yeah yeah and was was in the wrong place and then eventually did experimental theater and then started doing characters and liked that. Why do you think you were in the wrong place? I was a really bad dancer immediately. And I had been like belting in my room by myself for years and just happened to have a good audition for school. Yeah. And then, but like very hit or miss with notes. Oh, I see.

So, and then went to college around people that had like been on Broadway and were like, you know, musical theater darlings. And I didn't know that much about musical theater. I just knew that I loved to sing and I love to act. And then I found out I have vocal nodules in front of everybody. What do you mean in front of everybody? Well, you have to like... They came shooting out?

That's a nodule! Get out of here. You and your... That's what it felt like. You and your nodes hit the road. That's what it felt like you had to audition for NYU and then you find out if you're getting in. And then when you're in, I didn't. know, but you fucking re-audition

in front of your peers also. Oh, wow. So I had been waiting tables at a very loud restaurant that summer. And I think I maybe happened then. Yeah. And we, yeah, I had to sing my audition song, which I think was

on my own from laymiss and got made fun of for choosing a very cliche musical theater song. And then and then like couldn't hit any of the notes. And my teacher was like, you have vocal nodules. And she was right. Oh, wow. And then I had to keep singing in front of my peers in a head voice, which I've never

started before. And to me, sounds terrible. What does that mean? It means that like, and if, you know, you're singing a high note, sometimes you like belt it out and it comes like resonant from the chest. Yeah, yeah. And sometimes it doesn't. I see.

And it comes from here. You're just talking up in your nose. Yeah, yeah, yeah. And our voice teacher actually spoke up here. And she would, she would encourage us all. to just speak here instead that it was the healthier thing to do. Not need you get the chest involved. Right.

And so for two years in the training, they have you just like singing, like, properly like that. And I fucking hated it. Yeah. And I, like, couldn't hit any notes until the nodules went away. Oh, you didn't get there. It's not like a remove them thing. You can. Yeah, yeah.

You can. Yeah. I did some vocal therapy, and they subsided. Yeah, yeah. Yeah. Wow. So what, how does, Well, first of all, were you doing theater in high school, too? I was.

I was doing like community. Or was you're mostly in the room, like you said. Like in my bedroom. Yeah, yeah, yeah. Mostly that. Yeah, yeah. Mostly that. I did do like some community theater growing up.

Was there, were there like, was there theater kids? Like, were you among a group of like, theater kids? Yeah. No. It wasn't, it was, you know, I was desperate to fit in. Yeah. And the cool kids did hockey football. ball art was like, you know.

Ew. You do, you're in drama club? Oh, wow. Oh, cool. Yeah. Or the guy liked, you know, would be like, or you could like just come watch, you know, my baseball game or whatever. And I'd be like, cool, yeah, I'll be there, you know.

Yeah, yeah, yeah. As soon as I can. Were you the funny kid in school? Yeah. You were. Yeah, yeah. It was kind of the smart ass. So it all kind of played out.

And were you the funny one? I kind of, I wasn't. the funny one, but I was, you kind of seemed like you might have been kind of shy. I don't, I was sort of dual. Like I was a people pleaser definitely. Yeah. But I had an outgoing part of my personality and then I was, but I was fun. I didn't realize I was funny, but I was looking back on yearbooks and was like, you're so funny. You're so funny. So I had like a smart ass part of me. Yeah, yeah. Yeah. Yeah. Yeah. You know, about it, you know, whoever. But like, yeah, I didn't realize that it was funny, I think, for a bit. Because both my parents are very funny. My mom is unintentionally

hysterical and doesn't want to be and gets very upset if you laugh at her, which is a problem because she's, oh, she's so brilliant. It drives me insane. And then my dad was overtly funny, but, like, offended everybody. Did you feel any of that kind of like, you know, high school societal pressure to not be the funny girl? Yeah, I don't. Yeah, I think, yeah, exactly. There you go. You know what I mean? Yeah, exactly.

I was trying to be like the hot, cool girl. Yeah. I was too busy. And then the funny was just survival. Right. Survival. Because I'm earnest, because I'm gullible, because I have all of these natural traits, raise my hand too much, ask too many questions.

Yeah. That naturally put me in dork category, which I was, you know, all through elementary school. And then started to realize, like, okay, don't raise my hand, swear more. Don't tell people not to swear. That's a bad idea. Right, right. And don't do that. That's not going to help.

No, no. Did you say, yeah, exactly. And then, yeah, I started to like figure out how to pretend to fit in a little bit. And yeah, so I liked being funny, but I, yeah, I didn't want to be the funny girl. Right. And when you. Which is fucked up. Yeah.

Yeah. But I was pretzelling all over the place. I hope that there's. that that's less. I think it is. I think it must be because there's been just too many funny, strong women in the popular culture, you know. There's there are majors in school now about studying comedy. Yeah.

You know, I feel like that didn't exist when I was in my 20s. There's like a whole different reverence for comedy now. I think then there used to be. And improv too improv. Everybody's like every fucking high school has got an improv thing. Right. And I was like, that was kind of fringe, right? Yeah, absolutely.

There was, like in Chicago, the birthplace of improv, there was Second City, Improv Olympic, and then this other one that was called Comedy Sports that was very punchy, you know, sell two for one drinks kind of thing. Sorry, comedy sports people, but that was my impression. So, yeah, there wasn't, it wasn't like there was a ton of improv going on. There would be people who were part of those groups that would maybe do like a side show or something. But largely it was just that. And then like when the upright citizens brigade came to New York and, you know, those four people came to New York in whatever that was like 94, 95, there was nothing in New York.

There was no improv theater in New York. And it just, and that's why like the tri-state, the East Coast just, you know, gravitated towards them. It's, yeah, I mean, it's truly interesting. It's truly astounding what those four people did. And it's got to affect the nature of comedy being made. Absolutely. That it's mainstream now. Absolutely.

And like versus it being fringe. And I feel like that's sort of why I struggle in comedy in general now because I'm like, there's so many people doing it. And I don't know. The things that I respond to tend to be fucked up in a way that feels like how do you do something fringe now when fringe is like the norm? I don't know. Not to get too. You know, petty about it.

Yeah. I mean, my feeling is that you, since you're asking. I am. The best, I think the best mode of operation is to do what you got to do. Yeah. Do what's you. Do what's in you. And that when you strive to meet some sort of outside, like something that sells or something that's like the thing that's working now.

And throughout my career, I've worked with people like partners who I'd had like creative partners who would be like, You know, we, this is, we should, you know, that last script didn't do so well. We should write one that is like what they're buying. And I always was like, no, we should not. Right. We should not. Right. Because that, it won't be that.

And there are, that already exists. And so we might as well do what we are. And I see so many comedians that are like just a version, like, especially a lot of guy comedians. It's like, they're just a version of that guy. that guy comedian. And they do jokes and it's like they have material that is original, but it's just like the stuff that's working all over the place for middle comics. And I'm like, you have no interest in like finding out who you are and how you're different.

You have no interest in that. You're going to do an entire half hour of whatever, you know. Is that because there's money to make now and that, there wasn't? Well, I think it's because, uh, I think it's because it was, I was, I just, I just did, uh, Jay Moore's podcast and he told me did there's,

it's not kill Tony, but there's like skankapalooza or something. Do you know what I'm talking about? Yeah. Yeah. There's like, yeah, there's like a group of comedians now, you know what kill, well, there's, there's like these groups of comedians that are sort of clustered on the internet in different ways. Oh, yeah.

And most of the comedians that I know look down their nose at them. I see. And Colin Quinn was on one of them, which is called like, Legion of Skanks. It's called Legion of Skanks. And Colin said, Colin said, Legion of Skanks. Why don't you call it what this really is Lollapalooza for Middles? To their face? To their face on their podcast.

How do they react? I don't know. I just was hearing it from Jay. And it's like, and that's so fucking Colin Quinn, he's a fucking sword. Wow. But it is, that's the answer. It's, it's middles. It's middles and they're trying to.

But you can have a career doing that now. You can have a career. You can have a career. But I still maintain that you can be in middle and challenge yourself. Well, yeah. And try and do something different and not think about like what's going to work. Yeah. And think of it because it, the only good stand-ups in my est, well, the only ones that I'm really interested in are the ones that it's, where it's an expression of a person where you're seeing an

artist tell you about themselves. Yeah. And not being like this transactional back and forth with joke, laugh, joke, laugh, joke, laugh. That's so fucking boring to me. And when I'm, most comedy clubs, when I'm in there, you know, I don't go to them often. And when I do that, that, that transaction thing is just fucking boring and shit. Makes me very uncomfortable. Yeah. I also am the person that's like laughing too loud because I want to fit in. Partially, but I more so feel bad. Yeah, yeah, yeah. Like to because I think it's also really, well, yeah, they're like standing up there and admitting like I'm here for the transaction or many to make you laugh. And I find that really insane. Yeah, yeah. On many levels. And also to be honest that we've shown up to be like,

make me laugh, itch. You know, it's interesting. Like, I kind of feel like, I'm so sorry. You know what I mean? Like, you don't have to. Oh, I'm the one sitting in the dark. You're the one doing all the work. I should do something.

I guess. Going back to the fucking childhood, yeah. Yeah. Well, now you said you started doing experimental theater and that led to sort of character work. Is that when you met Maya was doing that kind of stuff? Yeah, we were juniors in college and we were in... Both at NYU?

We were both at NYU. She had been in the experimental theater wing for a long time, so she was already doing weird stuff. And I was still in CAP. And then there was a program in Amsterdam. Cap is or was a defunct or changed musical theater program at NYU. Okay. And yeah, there was this program in Amsterdam that's still going on called ITW. And it's like 25 students or something from all different studios.

And this teacher, Kevin Colkey, kind of leads you through it. And it ended up being a lot of comedy people like John Early was there. Rachel Bloom was there with us and then and Maya and I were there and and yeah and you just like you're self-directing or self-writing but it's not for one purpose. It's just like, you know, you get prompts and then you're doing it. Yeah, yeah. And it's improvised or it's written? It's like if we're doing, yeah, it's kind of hybrid like you're, if you're like, I sound like such a dork. If you're doing clowning or you're doing mask work. I see. You know, some people are very serious when they're doing it. And some people are fucking hilarious. And it is improv and they are

creating stories and they are like and so Maya did this mask work of an old woman and it was hysterical. And every prompt that she was given was really funny. And I ended up doing, you know, characters too and sort of like connecting to a part of myself that, yeah, just was unabashedly fucking weird and funny in a way that felt familiar. And I had never really seen that before. Right. And so, yeah, that was sort of an eye-opener. And then we went back to, you know, normal life and NYU in college, blah, blah, blah. And then we graduated and we both were kind of miserable in different ways. I was going to go back to school for something else. Which was? Probably like something like music therapy. Oh, you hadn't decided yet, yeah.

No, I was just sort of depressed and freaking out that all the loans that I had gotten and all of the, you know, promises I had made to my parents. Yeah. I'm like, I probably, like, I'll make it worth it, whatever. Where I was like, oh, I'm a failure. And really, honestly, the feeling of like, you know, me on my sort of high horse of like, if I'm an artist, you know, even if I'm living on a mattress and, you know, working 80-hour weeks and 40 of those are waiting tables, like, I'll be happy, you know, and then waking

up one day and being like, I guess, Josh. Yeah, yeah, yeah. You know, I'm exhausted. It sounded good, but it's kind of. It kind of sucks. It sucks. Yeah. My back hurts.

Like, yeah, I just was like, okay. You know, this is not the thing. I'm horribly depressed and like, what, where am I going with this? Yeah. And then I. And she was kind of going through a similar thing? She was doing a lot better than that. She was doing some regional theater and she sort of, yeah.

And she was, she's from L.A. originally. She went back home. She was like doing, she was, she was in a better position, but definitely had like, really high aspirations as I did that we were both frustrated by, you know? And, um, and yeah, so different than like obviously being in school and like doing your fucking Gratowski work and reading from the greatest playwrights and getting to do that. And then all of a sudden I'm like auditioning every day to say a word and a commercial and not getting it. Yeah. Yeah. And then getting it and being like, yes. Yes. Which celebrate. But then I'm going back home like an idiot and like preparing when they're

like, what are you working? Like, what are you acting? How's it going? And being like, yes, I just did a subway commercial. And I had a line. And I prepared that answer for, you know, a week or whatever. So I, yeah, it was just the time of being like, what am I doing? This is not, and not against anybody else doing it.

I just was like not happy. Yeah, yeah. So, and then I went away eventually in a dramatic way. I went to India and did cliche things of trying to find myself. Yeah, yeah. and started writing there and really liked that. And then convinced Maya when I got back to make a web series with me and play characters before I'd go back to school for something else.

Okay. But it was important for the engine of things to change for me of like, what do I want to do to the nature of exactly what you're talking about, of like, you know, it comes up now again and again in our being 38 now of like, what's going to sell? What do people like? Who are you? How do you fin the mold?

Blah, blah, blah. Yeah. That was very, very hard for me to like, to break. Yeah. That was just embedded into who I was. So that was a big moment for me to try to, try to, you know, do things the way that I wanted to do it for joy. Well, but also, I mean, you guys did. I mean, Penn 15 to say whatever, I mean, whatever age you guys were at the time to play, what were your 13-year-olds?

Yeah. That's fucking crazy. It was great. And that's what led to it, really. I'm sure that you sat across from people and pitched that to them and they were like, get the fuck out of here. Yeah. You know what I mean? Yeah.

Definitely. Yeah, everybody told us that it wouldn't work. And it was because of that time of going, like, how do I make things that we think are funny? What would you make if everybody else hated it and you loved it? And that was the motivation for it. What would you make? And that was like an incredible time. And I think something about moving to L.A., New York was so like, and I do love New York, but like highbrow in a way that I was trying to meet.

You know what I mean? And being like... Yeah, no, I know. It's... It was... The theater. Yeah. It's like...

And it wasn't... It was like... Yeah. And I was just... I was not who I was. And coming to L.A. was like, okay. Like, I can... Yeah.

It was just a freedom, I think. To like... But... But... And then sitting across from people being like, that's... What do you want to make in TV? You know, after we made our web series and... And hating everything we said.

Yeah, yeah. Yeah. And then... was there like one person was there more than one person involved interested in pen 15 because I can't remember really where was that it was that Hulu yeah um no I mean I remember we we we I think Fox 20th or something was attached at the time when we pitched it and there were like four places we could pitch to that they were making deals with at the time and it was Showtime HBO FX and Hulu and no I mean I remember Maya

holding up in the showtime pitch. This was a long time ago, so I don't think I'm adding anyone. But she was holding up a picture. We were basically pitching the masturbation episode where Maya discovers masturbation for the first time.

And there's a man. It's so fucking funny. Basically, I don't know. I'm like, I'm 38 now. I was probably in his 50s or something. Yeah. And you're like, oh, it's going to be funny. And she takes out a picture.

And she's like, that's me and that's my dad. And I have bows in my hair because right before this moment, I was masturbating. And he came home and I hadn't seen him in a long time. And I remember, she was like, and I just like put all of this, you know, bows to be like a little girl again. Say hi. And the Showtime executive was like, put the picture down.

I think I'm going to throw up. And, yeah, we were like, ha, ha, ha, okay. Yeah, yeah. When in the elevator, we're like, that went poorly. Yeah. And so, yeah, no, it definitely wasn't. like knocking down our doors. I mean, I think we all can agree on who the fucked up one was in that, you know,

in that little scenario. Jesus Christ, take it easy guy. Yeah, I mean, he was doing it with like a slight smile, I guess, of like, oh, my God, I'm going to throw up. Like, can you put it down? Yeah, yeah. But yeah, it was, it was definitely not a home run, you know. And nobody that we pitched it to were like, this is a winner.

Yeah, yeah. You know, Hulu was like, I guess. Yeah, yeah. Can you make it for nothing? Yeah, okay, you can try. Yeah, yeah. And then we're so, but like, I don't think it would ever be made now. Like, we were so, so lucky that.

Really? People tell me that all the time that it's a comp when they go into pitch things and that they're like, we would never make this now. But the irony is like I keep hearing that it's sort of like trending now with high schoolers. So there's a time when it was like just 30 year olds or my age that was stopping me. And then now it's teenagers. And it definitely seems like a show that can, you know. Yeah.

It can live again and again and again. end, you know. Yeah. I mean, it's so funny. It was so good. And there was so much, like, real kind of pathos mixed in along with it, you know, without it being preachy or anything. It was just like there was tons of real shit in there. Thanks. Like a picture of like, I had bows in my hair because I was just, it's just been masturbating. Yeah. And it should that we felt was funny. And I think that that was, it's so nice having a partner at times, especially I feel like in comedy and one, it's like more experimental. You're just like trying to prove yourself of like, okay, we're making each other laugh. Yeah. And if nobody else thinks it's funny, like, you're fucking dying. So that's fine.

Yeah. Yeah. And getting older is hard too in comedy where I'm like, I don't, I'm tired. Like, I don't know. Yeah. It does. Well, I used to, I used to worry about it because it is kind of like a young person's. I'm aware. I'm getting more aware of that now. It's a young person's game. Yeah. And but I mean, well, I mean, it's so fucking hard to judge now because there's not going on, you know, like there's so little going on. And so it's kind of like any, like any acting work that I do, I feel like, oh, yeah, this. I remember this, you know, because there's so many other podcasting and, you know, and then dancing with the stars shit. Right. Not shit, but, you know, like just dancing with the stars becoming this whole thing and there being like these sort of

attendant sort of jobs and things that come from that to where it's like, I guess. I asked my manager at one point, like I was doing all this unscripted, which is what they call the kind of reality. Oh, I'm no, unscripted. Yeah, yeah, yeah. No, I'm telling the people. Oh, sorry. Oh, okay, the people. Yeah, yeah, yeah, the unscripted. And it's, I'm like, is, I said, am I doing all this unscripted?

Is that going to hurt my acting career? He said, like, there's no acting. There's unscripted. That's what's there. So do that. And I'm like, oh, okay. Well, that's a good answer. Wow.

So it's, yeah, it's rough. How come it was only two seasons? It had been designed that way. I mean, it was supposed to be three. So basically like the two, they fucking called it two A and two B. And had us, we shot like 15 or 16 episodes block shot them. And then they ended up like making it all within one season. So it's supposed to be season one, two and three.

So the last season is two seasons. It's two story arcs. They were dropped separately, but it all unfortunately fell under season two, which was not something we were aware of when we went into it. So that's always frustrating where it's like two seasons and like three, three seasons. But still, like we, you know, it had been designed of like,

that was sort of the pitch from the beginning of like the 13 year olds, you know, are real 13 year olds. We are not. They're going to get older. They're not going to look like that anymore. That moment of the in between is going to pass. And this is part of, you know, the core idea. And then there was also the just the simple fact of like, and why I say like, I'm too old for comedy and too, I'm too tired is like it was crazy.

Like it was really low budget and it was 16 hour days for years and years and years without a break. And the most creatively fulfilling ever of like playing the characters and show running and being in post for 12 hours a day every day. And, you know, and then you're doing the interviews and then you're back. in the writer's room and then you're doing it all over. I mean, you're probably like, yeah, I know it's crazy. No, no. I mean, I asked the question and now as you're explaining it, I'm like, oh, yeah, okay, right. I understand. And then towards the last. Because you're on a fucking offshore oil rig, basically. Right. It's making a really funny TV show, but it's still, you're still on an offshore rig. Yeah, it was, it was, yeah, it was just like such a magical time.

It's so hard. So brutal. And then it was in that final. push of the writer's room and then pre-production and the beginning of production where I was flying back and forth from L.A. to Tampa where my dad was to be his like basically sole caregiver. Sure. So by the end of that, I was just like, we were all fucking exhausted. And then it was COVID. Yeah. And Maya and I had babies. Yeah. And there was also. Very competitive.

The babies. Yeah. No, you and her. I know. No, we happened. It was very strange. She told me that. they were interested in that. And I was like, oh, we're not for a long time. Yeah, yeah. And then I happened to be pregnant. No, no, no, no. It's just a funny story.

Yeah, yeah. I happened to be pregnant when she said that to me. Yeah. With my long-term partner, but it was really bizarre. And then I was like, I'm pregnant. No, when she told me, I was like, not for me, sister. Oh, not for a few more years. Right, right.

And then a month later. Right. And the fetus inside. You left. Left. Here I come. Surprise, you won't sleep again. So that was fucking crazy.

And, I mean, to be totally honest, it was also a conscious decision in that, like, we were best friends and we were operating. Like, it was just hard. Yeah. I mean, I'm sure a lot of us that have worked with partners for a long time, like, you know, get it. But it, it just, we wanted to retain the friendship. You need. Yeah. And she's still my best friend.

For years and years would ask me about, like, do you and Conan hang out? And I'm like, yeah. at work for fucking hours and hours and hours. Yeah. I mean, and we would sometimes socialize, but it's like, it changes it. We got plenty of each other. Yeah, yeah. You know, I love the guy and he loves me, but it's like, we got plenty of each other.

We don't need to go to dinner. Totally. Because also, like, what are we going to talk about the show? Well, exactly. And we were constantly fucking talking about the show. And we're both perfectionists and get obsessive. And so, like, yeah, we were just like always talking. about the show. Do you guys have plans to come back together for stuff?

I think we don't have plans. I think at some point we'll make something again together, but it's not soon on the docket. Yeah, yeah. How has motherhood changed your attitude about this fucking business? It's been a really strange thing because I, this was not really the, like I didn't have, I never thought in a million years that I, be playing a 13 year old around 13 year olds on television that I would be you know and then it would end and people would be like you're a comedian yeah cheers and I'd be like I know I am like I didn't you know I was just like I like doing characters I know what I think is funny is funny I know that

there's a lot that I don't think is funny and I feel strongly about that yeah and I like writing for people and I like writing funny shit but I'm not that felt strange yeah and And I think still what I reckoned with after Penn 15 was this feeling of like a comfort in the anarchy of making that show. For me, it felt very important spiritually as a writer, all these things to be like, oh, you all want me to, because I had done a Fox procedural called Rosewood. That was really great for many reasons. But like I was the funny person, DNA specialist in short mini skirts and a tan and putting in hair extensions for the first time in my life. And like, I, 1015 was the opposite. It's like we put on, we put on makeup here and there.

We added hairs. We weren't removing them. Yeah, yeah. We, I would come in like fucking wrecked from the night before of shooting for fucking 16 hours and looked crazy. And we were like, you know, record. Perfect. Yeah, yeah. And you just continued putting that out there and putting that out there and thinking for sure it would come out.

And people would be like, this is fucking disgusting. Yeah. And to not. some people feel that way, but to knock at that response was pretty incredible and unexpected. We were like, we're going to do one season. We better do all that we can and then they'll be done. They're on to us, you know? And like that was a fast and furious introduction to this town. Nobody really knew me, had an opinion of me, and then all of a sudden they do when you matter for a second.

Yeah. that's my real first introduction where it's like it just was bizarre. And then like buying a house and doing these normal things, having a baby, you have a mortgage, you have all these things. And how do I continue to like be in, let's just say, I mean, maybe that's a little strong to say, but like an anarchist in my work of like what I think is funny and like still pay my bills and still be a parent and like not be working 16 hour days every day forever. because it's super fucking low budget and I'll do whatever.

You know what I mean? So I have not found that balance. I still crave more of my own original work that is making something that I love that everybody else hates. That is the goal. And I think the book is in that realm for me, which is great. But I do want more of that. But it is a hard dance to find how to like.

Yeah. And again, it's a, it is. the most bizarre time and entertainment in the whatever 30 years, you know, 30-ish years that I've been doing it. It's just, I feel, sometimes I feel like it's not, like it's not Los Angeles. It's like, I don't know, Milwaukee. Like, sure, there's some production going on, but it's like Milwaukee production. It just, it doesn't, it just doesn't feel like there's nearly as much stuff. And I just can tell from friends, they're just not working like they used to work. So it is. It's very strange. It's very strange. And it's a, and it's a, it's a, it's, it's fucking brutal. It's fucking brutal. And you

got to have some kind of, uh, I was actually talking to my shrink the other day about somebody and I just was like, well, you know, if you're going to get in. into this thing. I don't remember even what the thing was, but it was kind of a work thing. And I was like, you're going to get into this thing. You just got to know that you can, you got to just be like, yeah, I can do this. I said, yeah, that's what you got to do. And he's like, well, you do realize, like that that is a strength of yours, that it doesn't necessarily apply to everyone else. And I was like, oh, okay, yeah. And I don't know where it comes from, but I've always had it. I've always kind of been, I mean, I've certainly, you know, I certainly have tons of self-doubt and not, and, and

plenty of not great idea of myself or not a tremendous amount of self-love at times. Yeah, but, but there, I always was kind of like, well, given an opportunity, I got to fucking do it, you know. Yeah. It's almost like for me, from working from an early age. Yeah. Because I started like with a paper route and then working for my stepfather's plumbing business and my mother had a kitchen business. And, you know, she remodeled and did contracting. And from working. And then the grocery store, you know, like, I, from working, to me, it was, I always was like, like, you don't fuck around. Yeah. On, and at work. Totally. You, when you get to work, you work. And, you know, and also, too, if there's something unpleasant at work, get it over with. Yeah. Don't fucking

dawdle. Don't, like, you know. Doddle. I love that word. Yeah. You know, like, fucking work. Yeah. And so for me, that was always kind of like, when I was given opportunities, I was like, well, they're paying me. Yeah. they must see something in me. Early on when I got jobs, it was always like, well, they, I'm going to trust them. Yeah. But I can do this. Yeah.

Because they said we'll give you money to do this. Right. I'm going to be like, all right. All right. It'd be rude of me to differ with them. You know, okay. I do relate to that weirdly, like jobs since I was young and you just fucking, you just do it. Yeah.

So the grindstone. But yeah, I don't know. I guess in that time of being in New York. and being like, yeah, nose with the grindstone. And then that revelation of like, oh, something has to adjust here. Yeah. I'm like trying to carry that with me.

Yeah. Maybe because my instinct is to just never pause or stop. Right. It would be like, you know, I don't know. Yeah, yeah. I don't know. It's interesting. It is hard and it is hard.

And I also do think that you, the two of you are in such an interesting position because, I mean, you know, the fact that they're saying like, this could never get made. Yeah. They didn't know what to do with you then and they probably don't know. They don't know. I love that. Yes. You have to know what to do with yourself. Yeah. And that is hard when you're. They're just puzzled by you guys. Yes. Because they're probably also puzzled by.

Why it worked. Why it worked. And also. I don't get it. It's not funny. Well, and also just the fact that like, she's ugly. Exactly. You're two beautiful women who made yourself ugly. Yeah. No, I do think that that's television. Preach, brother. You're just like, what the fuck is wrong with those gals? Absolutely. Absolutely.

And I think what's been weird for me is like, and the slowing down has to do with a lot of other things too, but it was like, I am inherently a people pleaser. What we do in Penn 15 is what I aspire to. It's the things that are in my mind that I grapple with quietly and have become more loud over the years. Or both my parents were hippies and different kinds. of thinkers and philosopher, whatever, like, they didn't fall into the norm. And, like, that's in me, but I don't operate that, like, that day to day. And so after Penn and you're meeting with your agents for the first time in a way that people care. Yeah. And you're like, I guess I could star in that Fox show. You know what I mean? I guess I am funny. And sort of not

caring myself clearly. And not knowing who, like, okay, so where does that freaky person, woman, girl, baby, boy, whatever it is, like still work here and does it? Or am I just here because I think I'm supposed to be or I'm seeking more applause or whatever. But this is why I have a therapist and wrote a fucking memoir because I overthink things. Well, speaking of it, the sane one will be published May 5th and you're going to be doing a book tour. Yeah. So people go to the internet and look her up. Please. The tickets can be found at Anna dash conkel.com, which is K-O-N-K-K-L-E. And yeah, it sounds, I'm going to read it.

Thank you. Or maybe I'll listen to you, read it. Okay, yeah. Let you do all the work. Yes, please. And I'm not going to say that it's also funny. People assume it's funny. You're funny, so they assume it's funny.

Okay. I should think. Okay. Trust me. No, no. I'm just kidding. No, it's not funny. It's not funny at all.

It doesn't have to be. Oh, Derek. Are you laughing at my trauma? Good. I love it. You hate it. I'm just kidding. Oh, all right.

Well, thank you so much for coming in. This was really nice. It's great talking to you. And thank all of you for listening. I'll be back next week with more of the three questions. The three questions with Andy Richter is a team cocoa production. It is produced by Sean Doherty and engineered by Rich Garcia. Additional engineering support by Eduardo Perez and Joanna Samuel.

executive produced by Nick Leow, Adam Sacks, and Jeff Ross, talent booking by Paula Davis, Gina Batista, with assistance from Maddie Ogden, research by Alyssa Graal. Don't forget to rate and review and subscribe to the three questions with Andy Richter wherever you get your podcasts. And do you have a favorite question

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