Mike Birbiglia's Working It Out - 76. Jessi Klein: This Is the Reason For Comedy

Episode Date: July 11, 2022

Jessi Klein is an Emmy-award winning comedian, writer, actor, and author, with a resume that includes Inside Amy Schumer, Saturday Night Live, Transparent, Kroll Show, and the voice of Jessi Glaser on Big Mouth. On top of all that, WIO listeners may remember her from Mike’s film Sleepwalk With Me where her character places a pizza pillow around Mike’s neck and then sprays him with tomato sauce. In this episode the two old friends punch up jokes and discuss why writing about being a parent can be a third rail subject. They also go deep on Jessi’s New York Times-bestselling book “I’ll Show Myself Out” and Jessi explains why the title of two of her book chapters are “In Defense of Drinking” and “Your Husband Will Remarry Five Minutes After You Die.”Please consider donating to Moms Demand Action

Um, Jessie, you and I have known each other for approximately 80 to 100 years. Yes, the length of a full person's life. Hey, everybody, we are back. That is, of course, the voice of the great Jessie Klein, one of my favorite comedic voices, comedians, comedic actors, actors, voice actors. You may know her from her voice on Big Mouth, which I love. comedians, comedic actors, actors, voice actors. You may know her from her voice on Big Mouth, which I love, from my buddy Nick Kroll.

She has written for Inside Amy Schumer and Vanessa Bayer Show. I love that for you, which is great. She was in Sleepwalk with me. She sprayed me with a hose of tomato sauce and put a pizza pillow around my neck, if you remember that scene from Sleepwalk With Me. I've known her for a long time, which is why we have this great conversation today. We talk about her book. It's called I'll Show Myself Out. She is a two-time New York Times bestselling author.

I love her new book. York Times bestselling author. I love her new book. Before we begin, I just want to throw out that I'm going to be in Sag Harbor, New York, with my new show, The Old Man in the Pool. And then the world premiere of The Old Man in the Pool will be at the Mark Taper Forum in Los Angeles for five weeks, late July through August, with the full lights and sound and design. And the design is really, really cool. I'm going to be in the fall in Pittsburgh, Cleveland, Toronto for four shows. I hear you, Toronto. I've heard all the TikTok requests for where I should go. This list is basically a list of where you told me on TikTok I should go. I was almost scientific or mathematical how I decided whether to go to which city. Atlanta, I'm going to Cincinnati, Columbus, Detroit, Nashville. I forgot to mention

that we just added that I'm going to be at the Ryman. It's so exciting. It's an iconic music and performance venue. Mesa, Arizona is gorgeous. It's a gorgeous art center and Salt Lake City. More to come. Join the mailing list at burbiggs.com. This conversation today with Jesse Klein, it's as good of an episode as we've had in some ways. I mean, I always say that,

but it's just so fun to talk to someone you've known for so long, and you have a shorthand with. We talk a lot about craft. We talk a lot about jokes. We throw a lot of new jokes out, and she's got some great slow-round answers. Enjoy my conversation with the great Jesse Klein! We're working it. I think one of the extraordinary things about your career,

and I always use you as an example when people are like, I want to go into show business. Should I have a day job that supports my aspirations? Or should I work in show business as try to be an assistant and an executive and this and that? You did seemingly the undoable, which is you were a Comedy Central television executive. And you pivoted into being a writer, author, creator. Well, you know, someone's got to dream the impossible dream. That's right.

And I choose me. No, yeah, I have a very weird path. I think, like, if I was going to, like, extract anything, I think the piece that feels very exotic is that I worked at Comedy Central in development behind the scenes in TV, which felt like very kind of like a big get of a job unto itself. Yes. But ultimately, I mean, I feel like I've talked about, I can't remember when I've talked about this before, but, you know, it really was, I was just someone who like.

On the phone with your aunt? Probably, multiple aunts. No, I just, you know, I was a person who couldn't have—I mean, I needed a job. I had to have a job. And I happened into that job. I mean, I happened into it insofar as I was always a huge comedy nerdling and fan and grew up watching. I was watching, well, it didn't grow up because it wasn't on,

once again, very old. But in my teens was watching a lot of Ha, which is what Comedy Central was called at the time. Oh, wow. And a lot of just any stand-up show on basic cable, that's what I was watching. So they were on vh1 and they were on ha and i got very obsessed that way and then when i graduated from college

i had no uh idea you know this is i graduated from college in 97 so i had no idea how uh you know this was before like people grow up now i feel like the young the youngs are like i could just become a comedy writer or become a comedy. The youngs, yes. The youngs. Well, they can go on social media and become instant creators. Yes, you can become an instant creator. Back then, there was no instant creator job.

There was no instant creator job. It just seemed like I, my mom was a teacher and my dad was a probation officer. And, you know, it was like, what are you going to do? Anyway, but because I had obsessions with those things when I graduated, I ended up hustling to get a temp job. There was one temp company that didn't make you take a typing test. Which one? Force One.

Mine was Lori Group. Before it was Lori Group, it was Lori Girls. So it was just for women, I think. Oh, man. I was a Lori Girl. That's right. I've always thought of you as a Lori Girl. Anyway, Force One didn't make you take a typing test,

and they also had an in at all those little Viacom networks like MTV and Comedy Central, and I said I wanted to. If I could temp anywhere, I like MTV and Comedy Central. And I said I wanted to, if I could temp anywhere, I would temp at Comedy Central. This is all a very long way of saying that I basically was just someone who needed a job and then lucked into a pretty cool job that I learned a lot from. And in the course of doing that job, learned a lot about what I wanted to do. But yeah, I wasn't there that long before I realized, like,

no, I really secretly do want to write and perform. And I just have this job that I got kind of golden handcuffed at for a long time because it was affording me living in New York. I remember talking to you at the time and I was like, you are one of the funniest people on the planet.

Stop. You were always funny. When we were in our 20s and I wasn't funny, you were funny. Alright, I'm not gonna do this with you. Well, that's very nice. You've always been funny. But no one was expecting, maybe because your expectations were so low?

You were always a great comic. I wasn't a Laurie girl. You weren't a Laurie girl by no means. But you were always funny, and I was like, Jessie, I don't even know if you'd remember this. I was like, when are you going to quit your job and just be a comic? Oh, no, I do remember. Oh, you do remember this? I do remember.

Well, I have to say, I mean, just in the spirit of like, just like how glad I am to be talking to you right now. This is such a, like, bright spot in my— Oh, be talking to you right now. This is such a like bright spot in my, truly been looking forward to this. But no, you, I absolutely remember that. And you have always been one of the most encouraging, supportive, like friends and just people to have in an orbit of, yeah, I like those words from you when you were like, you could do this. I was very scared to be doing, I just, confidence is not my strong suit, Michael. Oh, I read the book.

No, those things meant a lot. I read the book called Confidence is Not My Strong Suit by Jesse Klein. I'll show myself, subtitle, I'll show myself out. That was a working title for a while. No, the other working title was Husk, and then they wouldn't let me call it Husk, and I think they were probably right. Yeah, but I don't bring it up to toot my own horn

for saying you were funny, because you were obviously funny, and everyone knew you were so funny. But I bring it up to say, you're one of the few people who, I remember talking to you, and you were like, I can't quit my job. You're like, I cannot.

I cannot. Because I will be, my parents will lose their minds and they'll be really upset. It was less the losing of their minds. It's so funny that we do remember these conversations with some clarity. I just, you know, I think,

I mean, for me, I don't want to, I don't want to, like, woe is me, my story in any way. Like, I, it's not like I grew up in, like, horrible poverty, but I also didn't feel like there was a net. And I felt very deeply like, who am I to just go try to get some giggle job when my parents have sacrificed? Do you know what I mean? I've sacrificed so much and like, I can't ask them for my, I just was very anxious about it all. And I kind of, the only reason I want to say that is because I don't think it can be overstated how big that is for so many people, I think, who have creative dreams and want to do these things. That it's like money is a huge stumbling block, you know? Yeah.

I remember you worked your way up as an executive at Comedy Central, and I remember that. And you were doing stand-up. You were like nighttime job stand-up nighttime job stand-up yeah and then at the same at the same time uh at some point you made a leap into being a writer producer like what was that pivot and like was that hard to do, like, was that hard to do? It was emotionally very hard to do. I was in therapy for years, kind of trying to find a way. I'm a very risk-averse person, and I, um... It takes me, like, I kind of feel that I need to do something for years before I do it.

I'm kind of trying to reduce the amount of time between the feeling and the doing, and I'm still averaging about five years. Um, but, uh, so yeah, I had to really think it through. And then, um, the like little lucky thing that I jumped, I knew I kind of had to like jump to something and not just, like, a nothing. And so, again, this is a brag, but Comedy Central was doing a show, starting up a show called The Showbiz Show with David Spade. Oh, yes, yes. And Doug Herzog, who was the president of the network, who is just a delightful gentleman who I'm still friendly with to this day. who is just a delightful gentleman who I'm still friendly with to this day. I remember him talking to me,

and the showrunner of that show had seen me on Best Week Ever. Oh, wow. Yes. But that's a huge thing, too. VH1 Best Week Ever in the 2000s. That was a stepping stone. Well, because there was nothing else. You were on it, and Pete Holmes was on it.

I think John Mulaney was on it. Mulaney was on it. Yeah. There was a lot. Sherrod Small was on it. Yes. I'm trying to think of all the people, the comics. Paul Scheer was on it. Paul Scheer.

Michael Ian Black. I think maybe Donna Fineglass on Michael Ian Black. Yes, yes. There's tons of comics doing these little snippets. I desperately wanted to get on that show. They did not want me. They were no interest in me. Egg on their face. Yeah. Crows face. Shame on their show. They did not want me. They were no interest in me. Egg on their face.

Crows face. Shame on their homes. Shame, shame, shame. Just go chant. Anyway, so the point of the Doug mention was just that he was very kind, just in a world of remembering specific conversations that help bump you along.

And he was like, if they're asking you to go write on this, he was like, you should get out of in-between land. He was like, go do the thing. And it was very helpful to me. I'm always grateful to him that he pushed me along to accept. So anyway, that was my first writing job. And I sublet my New York apartment, and I went to write on this show, and that was my first writing job. And I sublet my New York apartment and I went to write on this show and that was my first writing job.

There's a line in your book that I love, Jessie, which is from a chapter called Your Husband Will Remarry Five Minutes After You Die. Sure, sure. Jessie, do we need to read the chapter after we've read that title? No. No, you're all set. I mean, you still have to buy the book. You, I mean, you have so many great chapter titles. I love this book so much.

There's a chapter called In Defense of Drinking. Yeah. Yeah. Well, yeah, I'm here to defend drinking. Clearly, I'm alone on this. No one else in this country is drinking. You have a line in this chapter called, your husband will remarry five minutes after you die, which is, as a wife, I can't help but notice that husbands tend to get remarried approximately five minutes after their wife's heart stops. And the reason I bring this up is, I think it's a generalization.

Okay. Are you trying to give me, is this a hashtag not all men moment? Yeah, yeah. Cool. This is my men's rights meeting that you accidentally walked into. I've got a Homer Simpson gif out. I'm going to sound like I'm just shilling for my friend Jesse because I love this book so much.

I love it and laugh out loud again and again and again. love it and laugh out loud again and again and again. And I read passages to my wife, Jenny, who also loves it. Husbands tend to get remarried approximately five minutes after their wife's heart stops. Yes. Made me laugh out loud so hard. I love it. It's, of course, a generalization.

What does it take when you're doing the math of generalizing for a joke? What's the math that makes the generalization worth it? Ooh, a great question. One that could only come from the mind of Mike Birbiglia. No, it is a good question. No, I'm really, I'm glad you're bringing this up because I feel like, you know, the book, there's a lot in the book about being a parent and specifically being a mom. But I, and so I take a few swipes. That swipes, but I make some comedy generalizations that might have little partial seeds and acorns of truth in them. Although, of course—

Partial seeds and acorns? But all kidding aside— Oh, you mean your third book, Partial Seeds and Acorns? Oh, my God. That is like a title David Sedaris would think about and then toss aside. He could do so much better. No, I think—but I think the point is, my voice is getting so high,

but I do think about it. I don't want, I want men to read the book. I don't want men to feel slammed in the book. I didn't feel slammed. I didn't feel slammed. I felt seen. I'm glad you felt seen. Well, you are one of Lori's girls again. Yeah. I do think deeply about it when I write a sentence that includes some kind of generalization. I think the only ones in this

book are maybe about men. But because I do think about people reading it and I do maybe about men but um because i because i do i do think about people reading it and i do think about men reading it and feeling like is this just someone who's just being a hater and i i guess i the the comedy equation i yeah i'm like is this funny enough to bear to bear kind of brushing up against generalizing and hopefully the things that are made it into the final book are and then and then the little acorns you know the things that i'm like well even if it's not hashtag not all men some men i do i do think um you know having become a boy mom uh isn't that so gross and people are like, girl dad, boy mom, whatever. But just watching a,

I have a son, and then, you know, I'm watching, just changes your, the way you sort of think about what boys are like or girls are like, and, you know, I just, I do think men are better at compartmentalizing is all I'm saying. That was a long walk. That was a long walk.

That was a long walk. But I agree with you. I have a similar logic that I go through because so much of comedy is making an observation and throwing it out on stage and being like, is this funny? Or throwing it in your book and going, is this funny? Are you guys just so mad? Are you furious? Yeah.

But what I found, because I wrote the new one, the new one, Painfully True Stories from a Reluctant Dad with poems by J. Hope Stein. Loved it. And so I don't know if you found this, but I found writing about parenting to be the biggest third rail topic that I had ever written about. I had no idea that it would be the case. Yeah. It's funny because I don't think

I've used the phrase third rail as much as I have in talking about this book,, it does feel apt. And I think like part of what the book is about is that I do think for, I can't speak to the dad experience, for the mom experience, I think it's, it feels very dangerous to say things out loud about. Yes, about parenthood. Parenthood. And I think specifically for mothers to say kind of almost anything that brushes up against the notion that you're not loving every second and every dimensional aspect of being a parent feels like you are inviting being shamed as a bad mother. I'm not even joking. No, I'm laughing out of catharsis, not out of the joke of it. It's so true. Like, it's absurd. Yeah, I think it's so, um, it's

yeah, it's really wild that, I mean, even just since the book came out, it's been actually very, on the one hand, both very touching, and in some ways it does also make me a little sad because the number of women who've written to me or who came up to me at book readings and are like, thank you for writing this. I feel so seen. I feel like you're saying

things that I truly feel like I'm not allowed to say. And so the sad part is just like this is so crazy that our idea of motherhood is so um it's just so inhuman in a way that everyone no it's it's amazing that you're not allowed to have like um like what i've i guess i've been calling like an and experience which is is like, I love my child, and I am finding this very hard, and sometimes I need a break. That's the clip. That's the clip right there. And an and experience. I'm having an and experience.

This is going to be a TikTok viral sensation. This will be my big TikTok debut. Keep me away from there. You're absolutely right. You're absolutely right, though. It's like in my book, the new one in my show, there's like this dark night of the soul moment where I say, I can't believe my own thought. I get at this really low moment, I think,

I get why dads leave. And I go, I'm not going to do it, but I get it. And a majority of people, like you're saying, they go, I feel seen by that because they're like, you're saying this dark thing that you felt and you're not going to do. And, but then like this very small group of people, because eventually, you know, if you put something out in the world, enough people see it where some people are like, no, I hate you for saying this thing that makes me feel bad or feel like you're a bad dad and want to judge you being a dad. And what's amazing is, like, I actually think that's the best part of the book and the best part of the show.

Yeah, I mean, it's so interesting because I, yeah, I related to that. And I think, like, if the amount of blowback I think that a woman would get for saying that, like, you think about leaving is one million times more. Just because, and again, I'm going to have to keep hashtagging not all dads. But, like, clearly, culturally. I don't think you understand how hashtags work. I don't. Culturally, and I'm fine with it. Societally, like a lot of dads leave, you know? I mean, we all know people like—

I know so many people whose dads left. Like a ton. I mean, I could probably tick them off. I can't think of one person I know whose mom left. It's just not, it's just like, it just feels unimaginable. But that is not to say that moms don't also have that feeling. I think it's, you would be crazy to not because it's so hard. And it's okay to just admit.

I think it takes so much pressure off. I just, I think the sadness I feel is that I think women feel like that's such a deep secret they have to hold, that they have that feeling. And I mean, there's nothing worse in the world than feeling like you have like a dark secret. It's terrible.

And if I think if women were just allowed to say like, this is an absolutely normal thing that we all feel, I think it would lift like a tremendous amount of shame and guilt off of people. I totally agree. Like when I'm reading your book, I'm like, literally, this is the reason for comedy, this book. No, for real, for real. I'm like, people need to read books like this to have a catharsis of like, oh, it's not just me in a parking lot, you know, listening to Lemonade

before the store opens to pick up like a toy for my son or whatever, feeling like, I don't know what the exact toy was or whatever. It was balloons. I screwed up his birthday party. Yeah, yeah. I forgot how balloons work. Among all the hashtags, I don't know how they work.

Balloons, I don't know how they work. I'm really quite stupid. Yeah. But reading that is just like, there's so many of those moments in your book. It's just chock full. It's just wall to wall truisms, things that are true to you that you're confessing to the audience and it's cathartic.

Well, that's so, that really means a lot. Again, especially from you and having watched your show about parenting and feeling like you also, like, you know, were so vulnerable saying the things that, like you just said, like, people react. They don't always like it. But I think way more people are appreciative that, like, something has been said, you know. Yeah. Well, you were saying in your book, in the drinking chapter, this is the in defense of drinking chapter. Yes.

That you had some pushback from when you published in your last book a chapter about when you got an epidural. Yes. What was the pushback like? Like, what was it? It was just a chapter urging women to, you know, if you're on the fence, to if you're going to have a baby, to get that epidural, which was something I knew that I wanted from the jump. Yeah. And basically told, you know, well, I could go on and on, but the short of it to your

question was that chapter was— okay, I'm about to say a word that I have so much trouble saying—excerpted. Okay, wow. It was excerpted. This is getting very, very sophisticated. It was in—before the book came out, it ran in the New York Times in Week in Review as an opinion piece. Times and like Week in Review as like an opinion piece. And it kind of went around and it got like way more comments than, you know, just a lot of people were weighing in on it. And I would say about 65% of the comments were like mainly women just saying, thank you for writing this. And this is so nice.

But then the remainder were, there was a lot of anger. Did you notice how I wasn't quite sure what? I like that. What's the remainder? 65 out of 100? Yeah, sure. 35. The remaining 35%.

Yep, yep. I got so nervous. I just said the remainder. I meant the 35%. 35%. Yep, yep. I got so nervous I just said the remainder. I meant the 35%. 35% were people kind of yelling at me that I was like a bad mom for getting an epidural.

There were a lot of men telling me about what their wives did and how amazing their wives were, that they had quote-unquote natural births. And I was like, it's so interesting that you're the one who has the time to get online and yell at me. So annoying. natural births. And I was like, it's so interesting that you're the one who has the time to get online and yell at me. God. Yeah, people were mad. People got mad just saying that, just for me saying, I think like getting pain medication that's readily available to help with labor. People were mad just at that and saying I was a bad mom because of that. Like, why have a child if you're going to do that? How do you possibly compartmentalize that? Me? Yeah, because, I mean, I can't. I mean, I don't know about you. I literally, like, when people say stuff about the new,

you know, in the new one, I'm basically like, I have a really hard time being a dad. And sometimes every now and then people are like, yeah, you suck at being a dad. I'm now and then people are like yeah you suck at being well easy you know i don't want to fight yeah yeah i don't know i'm always like i told you well well i'll tell you i mean i think um what it's not what helps what or what's nice in a world of like you were saying, like what's comedy for, like extracting from that. Like why am I here?

What am I doing? Like why am I trying to be an artist? There, I'll say it. I think we're artists. Wow. Wow. Like to this day, I still also have women saying to me, thank you for writing that. And I forwarded this to like my, you know, my sister who's about to have a baby or my daughter who's about to have a baby.

And like I hear, I still hear from a lot of women, thank you for writing that. And that gets you sort of through all that. Yeah. I mean, also it's, you know, in a world where, you know, we live in hell. Yeah, I mean, also it's, you know, in a world where, you know, we live in hell, I'm like, I can survive people like some dumb men nattering at me online. Fine. You're probably most often recognized from putting a pizza pillow around my neck in a movie, Seabob, isn't it?

I am. Oh, my God, yes. I am. I get stopped in the street all the time. Do you have a positive memory? I remember filming that. It was the most fun I've ever had in my life. It was weird. You sprayed me with real tomato sauce. I sprayed you with real tomato sauce using,

speaking of, you know, an amazing crew, prop people. The prop master was amazing. That was, like, there was a lot of science. There was STEM, science, like, there was a lot of science and there was STEM. Science, technology, engineering, math. Went into that. There was STEM, for sure. Tomato sauce spewer.

Well, it was a whole mechanism where you were spraying me with like a hose of tomato sauce and then around my neck, for people who haven't seen the movie Sleepwalk With Me, there's a dream sequence where Jesse. So for no one. Jesse. So for no one. Jesse puts an actual pizza pillow around my neck in the context of a dream because she's another comedian and my subconscious, that's what happens. And then we're like almost going to make out

and then you spray me with tomato sauce. That's the whole scene. What a scene. But it's a riot. No, it was, I mean, it was truly, it was just so fun. It's such a crazy, it's such a crazy

thing that we did that. It's very, very strange. I mean, when will our kids watch this movie? Well, that's a good question. And when will they get married? Oh my gosh, Jesus Christ. What has happened to this interview?

Okay, so this is the thing we do called the slow round. What's your earliest memory when you were a kid? Wowzies. Yeah, I was thinking about just my earliest memory in general. There's a few images. I feel like I remember, like, sitting on my grandmother's lap at one point and, like, nuzzling in on my grandmother. And then, like, I always liked to, like, I like touching, like, earlobes and, like, you know, I was touching, like, the inside of her arm. And noticing that, like, her skin was, like, really loose because she was the middle person.

Yeah, sure. And I was like, what's going on here? Right. this what are bodies what are bodies doing uh i remember that being fascinated by my grandmother's old inner arm skin i remember um gosh that's like an early one i remember also i remember a moment where i must have been in my crib and i had a bad dream of some kind and woke up and there was like some kind of plant casting a shadow on the wall. Oh, my gosh. And just being terrified of a plant casting a shadow on the wall and thinking like, that's a monster. What can I do? How do I get out of it?

Like something. I mean, I just remember being like, I am rat-fucked by this plant shadow. I'm so scared. So you've avoided the question by answering with scenes from Pixar films. I mean, there's a reason Pixar does so well. They really nail what we all have.

What is your, in your family, in your family growing up, what was your role? Woof. Why? Is this woof to the questions or woof to the answers? I don't know. It might be both. I'm a very classic, I think, classic middle child. I was always trying to be the peacekeeper and make people laugh and have a good time.

And just trying to, yeah, trying to, hey, everyone, let's all chill out, right? Yeah, keep it light. Let's keep it light. Hey, let's keep it light. Let's keep it light. Has anyone heard? keep it light. Let's keep it light. Has anyone heard... Let's just do Thanksgiving. No, go off.

That's a woof. Yeah, that was very much, I think, my role was to just try to keep it light, not make waves. Let's just get through this. One of the funniest things about being your friend and knowing you so long is talking to you in this context of an interview

that on the page you're so confident in your words and then you're a shit interview. You're a mess. No, not your shit interview. That I'm like, what's your role in your family? And you're like, uh,

what? It's like you your response is so different from this persona in this book. No, the woof, the woof was just thinking, I was, I think I honestly just immediately went to, to the, to the trauma place of remembering the various fights and static I was breaking up all the time. What's the best piece of advice you've been given in your life that you used? This is also very funny because it's like, oh, we're having a banter. Fun, fun, fun.

And then you're like, Proust questionnaire. With no ramp. What's the best piece of advice in your life ever that you've used? Christ. Is it Proust? No, it's Proust. I think Proust is right. What's yours?

If you say yours, maybe I'll remember mine. Do you know yours off the top? I feel like if you say some things, it'll charm my nose. I think the best piece of advice I've been given was I had a screenwriting professor in college who goes, just make these scripts that you're writing. Just make a short film. Just make a thing, and then you'll understand what it is. And so I made, like, for essentially, like, I made, like, a no-budget short film in college that was a debacle. And it was, Jessie, I can't tell you.

I need to see this. It was so bad. Get it to me. No, no. Get it to me. It was so bad that the editor stole the tapes, the mini-DV tapes, and never returned them. No! That's how bad it was.

So these are out there somewhere? Oh, yeah, they're out there. They're on the black market. Oh, man. I would pay any amount of money under $200 to see these. Under $200. Yeah, no, that was the best piece of advice, is, like, sort of do instead of sort of, like, ponder, essentially.

Oh, my God. I feel like you just changed the course of my life with that advice. Because that is, like, I think the thing I struggle with the most. That's such good advice. For real? Oh, I ponder way too much. I feel like, yeah, I'm in my head about doing something. Just, yeah, I'm not, it really affects my,

I mean, I think it's also just I accept a little bit that's who I am. Like I'm a hand wringer. I'm not super prolific. I've tried to get better at it. I will say, I will say that's one thing I also did learn from working with Amy Schumer for so many years, because she's so good at just doing something, like just making something. Yeah, she's a great creator. She's a great creator and just like is impulsive in a very good way about just following

like let's just do something. I mean, I think in some ways that was why like we had a good balance of stuff. Yeah. Did you have like an odd personality from your childhood

who you knew that you think about a lot still as a grown up? Yes. I mean, also I grew up in up in the village in the 80s, and so everyone around us was really weird all the time. Oh, yeah. That makes sense. You know, it was a real environment to be in.

It's a little... I mean, yeah, it's a little hard to describe, but it was just such a specific time and place. It was like super, super artsy, right? The village in the 80s? Yeah. I mean, I think now people think of it, you know, it's become so like mallified. And it wasn't like that at all.

And it was a lot of artists. But also like New York City in the 80s. Like it was a little more of a lot of drugs. Yeah. But just a lot of characters. Let's just say there were a lot of drugs. Yeah. But just a lot of characters. Let's just say there were a lot of characters walking around. The other night I was walking by the comedy cellar and this guy goes, you wanted Coke, right?

I swear to God. You wanted Coke? I go, no. He goes, I was thinking of someone else. I was thinking of someone else. I was thinking of someone else. That's a good way to sell Coke. That's so funny. That's a good way to sell Coke.

Because I also feel like— You want a Coke, right? You do sort of like as a gestalt of a person, you're like one frame away from a guy, from looking like a guy who's doing a lot of Coke. Sure. You know, there's like a certain Mike Birbiglia type, just one edge over,

who is walking around the village getting coke to this day. Wall Street Mike Birbiglia does coke. Wall Street, like a Wall Street Mike Birbiglia. Show business Mike Birbiglia does not use coke. No. Some of the things we do on the show is we work out material. And this is sort of half-baked things, ideas, things I'm working on, things in my notebook. I love it.

And we can talk about what it makes you think of. We can talk about what could be better about it, what could be worse. Here to riff. Here to riff. Here to riff. Here to riff. My dad, in the same sentence, will say, I hate computers, and can you fix my computer? sentence will say, I hate computers and can you fix my computer?

You know, my mom, who's very, she's on her computer all day now. She is like a real, she's on the internet. Yeah. She, I find this very cute and sweet. She will call, she refers to her computer as computer. So she's like, oh, like, well, if I call her, like, sometimes I'll be like, she's like, can I call you back? I'm just on computer right now. She's on computer. It's so sweet. Um, so my, we, so my brother and I often have my, my the Apple Genius Bar, and it's hard to explain to your dad that you don't have 70 minutes free in the middle of the day to configure his SMTP server and figure out his Apple password. And I'm sure Joe and I have this hunch that at Apple Genius Support, there's a photo of my dad.

Like at the grocery store, there's a list of people not to take personal objects from. Oh, my God. But it says, do not help this guy install printer drivers. He does not know what a printer driver is. In fairness to your dad, it's way harder than it should be. It is. It's way harder than it should be. You know when you encounter some piece of technology or just something that, like, when a printer just works?

I mean, it's like an orgasm. You're like, oh, it just worked oh my god that's that is so dead on you know what because it almost never happens it is like it's like a one-night stand like an amazing one-night stand where like someone just knew exactly how to touch me yes that's like me and that printer just just our bodies fit together. That's great. I mean, of course, if it does become a bit, that's one of the great tactics, I think, of joke writing is like what are the different points of view? It's like playing the point of making fun of my dad,

but then the counterpoint of like he's right. You know, it never works. You got to use every part of the animal. I love that. Nose to tail. And then I have this thing about my dad, which is that my dad's one of these people who maybe shouldn't have a cell phone.

He only uses speakerphone, and he sort of shouts into it regardless of who's around. It's like a walkie-talkie. He'll be like, I'm at the Olive Garden. Over. Oh, my God. You know, my dad still doesn't have a cell phone. Oh, that's refreshing, I think.

No, really. It's like you're out on, they're still in New York City. He's, you know, he's like going to be 82. I'm like, could you maybe just get a cell phone? That's better than a father with two cell phones. You know, I will say do you have two my mom has like five email accounts oh yeah i could see that i just have one i'm like i have or i guess i have two but really like i don't care but she's like she's so she's like on on like a primal defensive stance

about like what could come into that inbox she's just like no that's for this I'm like it feels a little it is a little

drug dealer-ish I'm like what are you dodging that's very funny yeah no we all maybe we all like have an email account

that we're gonna discover someday and it's like those were the real emails where yeah oh my god all along email account that we're going to discover someday. And it's like, those were the real emails. Where? Yeah. Oh my God, all along it was Mike Berbiglia at Gmail. It's like an email

from Steven Spielberg, like, I love your work. I mean, I will say I, you know, talking about, you know, being a parent and getting to be a middle-aged, not getting to be, I'm a fully middle-aged person,. Like, I don't know how to do this or that. And I'm so, like, embarrassed. And I'm also kind of accepting of, like, let the long slide begin. Some younger person will help me with it. I don't know. Yeah.

Okay. Tell me if this is a joke. I wrote this in my notebook. Okay. I'll tell you. I've never woken up and thought, today's going to be fantastic. I consistently wake up and think, I should make a list.

You know, wait, is there more? Sorry, I was already laughing. That's like the joke part. And then the rest is like me being like the rest of my thought process, which is like, because otherwise I'm going to forget to do anything at all. Maybe I should stay in bed.

This is all very scary. I mean, that feels like, it feels great as the beginning of a book or a show to just be like, I never wake up and think this is going to be fantastic. This is dark, dark, dark, dark, dark. But I remember a Marc Maron. This was like seeing Marc Maron at like Luna Lounge in 1924. I recall. Back in the 20s at Luna Lounge.

I just remember him talking about how anxious he feels and like how everything feels so unbearable and he's so miserable. And then at one point he's like, and then he's like, and then I'll just remember, oh, I just get calm and I think, oh, I could always kill myself. Oh, yes. I remember that. I remember that joke. And I was like, it was, I mean, I'm not telling you well.

But, I mean, you know the way Mark can do what Mark does. It was like a very, it encapsulated Mark's Markness. I was lucky enough to see Mark at Luna Lounge in the 90s because my sister Gina introduced me to all that kind of alt comedy scene. Gina. He was really on fire.

I mean, he was... In those kinds of rooms, like the 70 people packed in a room in the East Village, holy cow. That was like what I spent... I mean, so I started working

at Comedy Central as an assistant in 1998. mean so I started working at Comedy Central as a as an assistant in 1998 and so I would just go I would just go be at Luna Lounge all the time and see like you know just see Mark and Sarah Silverman

Zach Alphanakis used to drop in Ross Broccoli do you remember Ross Broccoli? Oh my gosh yes. Reverend Jen. Reverend. That was the first time I ever did stand-up was at Reverend Jen's open mic that you paid $2 to participate in.

I think it's possible you and I were on a Luna Lounge lineup together. I think it's entirely possible. I recall something like that. Wait, I want to hear more of what you're working out. All right, so then this is a half an idea. The other night I had sex in my dream. Count it.

I count it. Is that a punchline? Oh, yes, it absolutely is. It counts. Count it. Yes, it absolutely is. It counts. They count it.

And I had sex with someone in my dream. And a few hours later, I woke up and I ran into the person at a coffee shop on my corner. And I thought, I just had sex with you in my dream. And what I said was, nice to see you. And now I'm suspicious of anyone who says nice to see you. You know, all right, I love all of that. Also, I had a dream. I can't remember. In the last few years, I had a dream where I was,

I truly, I would say if I can, I cannot remember who the object of the dream was, but some real man. And I was, anyway, I was masturbating in the dream. And then I, like, because I was so attracted to the guy, then I woke up and I was like, you loser. You won't even, like, let yourself just, like, have sex with a person in your own dream. You're still jerking off in your dream. Honestly, I was like, that is pathetic. Pathetic.

I love that. Pathetic. No, I had one where I had sex in a dream, or I was about to have sex in a dream, and I said to the person, I think this isn't going to work out, because even in my fantasies, I know my limitations. This is a true story.

I once had a dream. My husband's from Boston. He's a huge Patriots fan, whatever. He's like a huge Tom Brady fan. Anyway, I had a dream. I truly had a dream that my husband was having sex with Giselle. Oh. And it was so vivid.

Tom Brady's wife, a former wife maybe? Tom Brady's wife, Tom Brady's current wife. Okay. I woke up and had that. You know, it's like when things are so vivid and I was like mad. And I told my husband about it. I had a dream we were having sex with Giselle. I'm really mad at you. And he goes, I would never do that to Tom Brady.

Oh, that's too good. Fine to ruin my life. Oh, I love it. Would not do it to life. Oh, I love it. Would not do it to Tom. Whatever, Tom. Tell me if this is anything. Okay.

I was in an airport bathroom, and there was a man at the urinal with one hand holding his phone and the other hand holding his penis, and he was on speakerphone, and the accuracy of his penis was very low. He was not hitting the urinal all that much. And he shouted into the phone, I'm at baggage claim. And I thought, this man needs to be more honest with himself about his life.

This is not a true story. True story. Absolutely true story. That's straight to the notebook. I don't know about you, Jesse, but, like, I just write it all down. You gotta write it all down. I mean, a lot of these things, like,

I don't have a joke, really. It's just sort of a half-thought, and then maybe it becomes something later. Well, I still haven't remembered the life-changing advice I've received, even though I feel like I've gotten so much good advice over the years. But one piece of advice that I do give to, when asked, which is almost never,

but to aspiring comedians, writers, what have you, is that you must not just write everything down, but you must write it down as quickly as possible. Yes, I agree. Because you will forget. You will forget. Even the thing where you're like, there's no way I'm going to forget this. I know I want to write about this. I know I want to make a joke about this.

It's so funny to me. It's such a crazy thing. I will absolutely remember. You will still forget. You will still forget. You will still forget. You've got to write it down. Turn me into a Muppet. Write it down. I feel like this is us. Write it down. You will still forget. Write it down. You will still forget. Write it down. You've got to write it down. Turn me into a Muppet. Write it down. I feel like this is us. Write it down. Write it down. Write it down. This feels like the dynamic of being at a baseball stadium where like half the stadium

is trying to start the wave and the other half like won't accept the wave. Okay. I'm going to end on this because I think this is right up your alley. Okay. In terms of just subject matter, especially with your book, I'm going to end on this because I think this is right up your alley. Okay. In terms of just subject matter, especially with your book. I'll show myself out, which is brilliant. I feel so lucky to have found my wife, Jenny. And we both feel like we married up, which I feel like is the great illusion that keeps marriages together.

And recently we were at dinner with a couple and they said, we both married down. And I thought, you shouldn't be married. Wow. That's a second woof. I know it's a woof, right? I mean, knowing both you and Jenny, I will say

one of you did marry up and it was you. It was you. That's 100% true. She's a full queen. She's a queen. You're both amazing, but she's a queen and you married up. She's unbelievable. She's unbelievable. I always say about Jen, and I've never been able to formulate this into a joke or even a piece of poetry that when I see a film or a play or read a book,

there's no one's opinion on earth I want to hear more than my wife, Jenny. She's so brilliant. Will you help me remember? So when I saw your show, you read some of her poetry in the show. And she has, there's like maybe four lines of poetry in my life that like, I mean, I love poetry, but that penetrate into my brain and like hit my, like explode in my soul, you know? And she has that line about everything else is outer space.

What's the first part of the line? Yeah. A newborn rests her head on the earth of mother and father. Everything else is outer space. Decimatingly good. That's a J. Hope Steiner original. So beautiful. Thank you for sharing that. Thank you, Jenny, for writing it. Married up. married up.

The final thing that we do in the show is called Working It Out for a Cause. And we donate, or I donate, to an organization that you think is doing a good job. We link to them in the show notes. We encourage people to donate to them as well. Well, I love to donate to any pro-gun safety cause. There's obviously

Moms Demand Action. It's a great one. Yes, Moms Demand Action. Moms Demand Action. Or Everytown. Okay. Yes. We will contribute to both.

Love that. We have in the past, Bill Hader, he suggested Everytown last year. He's been giving to them for a long time. And yeah, we'll give to those both because clearly they're

doing great work in a time that is completely, completely horrifying. Jessie, I love your book. Thank you. It's so beautiful. You're just doing God's work with this comedy writing. Oh, my gosh.

Well, thanks for encouraging me in 1928. Cutting this out. Cutting this out. No. I'm being silenced. I'm being silenced. As a woman, I'm being silenced. Okay, we have to keep it in.

No. Peter, we're keeping it in. It means a lot when your peers encourage you, and I thank you, and thank you for having me on your podcast. This is awesome. Cutting it out. Oh, my God! Sorry, we're cutting it out.

That is a perfect sketch unto itself. Just a man being like, cutting it. No, every time you try to speak, no, it's going to be cut. Working it out because it's not done. Working it out because there's no hope.

That's going to do it for another episode of Working It Out. Jessie Klein, again, I couldn't recommend more highly her book, which is called I'll Show Myself Out.

Get it at your local bookstore. Support your local bookstores out there. Our producers of Working It Out Are Myself, along with Peter Salamone and Joseph Birbiglia, consulting producer Seth Barish, sound mix by Ben Cruz, supervising engineer Kate Balinski, sound and video recording by Gary Simons, Josiah Kosher, and David Urzua. Associate producer, Mabel Lewis. Thanks to Mike Insiglieri, Mike Berkowitz, as well as Marissa Hurwitz and Josh Uppfall.

Special thanks to Jack Antonoff and Bleachers for their music. As always, a very special thanks to my wife, the poet J. Hope Stein. Her book, Little Astronaut, actually, is coming out in September. You can follow her on Instagram, at jhopestein. Our book, the new one, is also at your local bookstore.

Support local bookstores. Of course, a special thanks to my daughter, Una, who created the original radio fort and taught me about so many things, but sound, sound as well. Thanks, most of all, to all of you who are listening. Tell your friends. Tell your enemies.

I mean, look, we don't have a lot of enemies in this life, if we're lucky. But let's say you find yourself at the grocery store and you spot some blueberry muffins and you reach for them. And then someone else touches those blueberry muffins at the exact same time. And they're gorgeous. They're gorgeous muffins. And you make eye contact. And what I'm urging you to do is to do the right thing and slowly pull your hand away and then make eye contact and say, I want to tell you about a comedy podcast where comedians

share their process and they work out new jokes. We're working it out, everybody. We'll see you next time.