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Tom Segura, a comedian known for specials like Completely Normal and Sledgehammer and the creator of the TV show Bad Thoughts. He's been on Conan and the Late show with Stephen Colbert, and he's here to teach us about how to write comedy. What makes Tom's humor so distinct is how observational and story based it is. He's the kind of guy that can look at something you've seen a thousand times and say, oh, my goodness. You ever noticed this? It's absolutely hilarious. And you're like, yes, it is. And so I said, dude, you gotta come on the show to teach us how you find jokes like that and write them. No, it follows. Here's his answer and a few moments that had me in tears of laughter. As you walk through the world, do you feel like you turn the comedy thing on and off as you're looking at the world, making observations, or is that just something that's always there in terms of how your brain works?
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I feel like it's there and it's whether you are engaging that muscle. It's kind of like the muscle right, where you're like, you can sort of focus on it, you know, channel some energy towards that and you can choose not to. I, I feel like it might sound silly, but like the best thing to do if, if I think if you're a comic is honestly talk a lot. Like, you're like, you're gonna say more funny things if you're talking more. You know, it's a version of like trying things. Like, you, obviously, you try it on stage, but even off stage, it's like when you, you have certain friends that you just like spout off to. And like, the more you do that and you're, you, you develop this kind of skill, I think, over time where you realize when you're in conversation and you say something, you're like, that's a thing. Yeah, you know, that, that becomes like the. Honestly, like the biggest muscle of it all, I think is recognizing, oh, that's something. Versus I'm just kind of shooting the shit, like just talking with you. Sometimes you get you, you something has legs. And you develop the skill of going, that's a thing.
A
How much of finding jokes you think is being a little bit kind of irritated, agitated, kind of like pissy about the world. Like, I think of Seinfeld and Larry David. Yeah, that seems to be like a
B
core thing of what, 100%, like being annoyed is funny. My 7 year old's annoyed all the time and he's hilarious. And it's also like, why are you so annoyed? But then he's just like, what's this table doing in the middle of the room? I keep running into it. And you're like, oh, that's like a. That's a funny perspective to have to be bothered by furniture. You know, like, he's. He's naturally funny, but, like, complaining is funny. What's not funny is total indifference. So, like, you. You figure out that when it comes to being funny, you have to have an opinion.
A
Yes.
B
Right. Like, you can be like, this is the best coffee I've ever had. And you can make that funny. This is the worst coffee. But if you're just like, it's good. Like, that's not. It's not funny to be like, it's fine. I don't care. Like, that's not funny. It's funny. If you go, this tastes like. Like somebody into a cup and boiled it. That's funny. Or if you're like, this is God's gift to the world. I wish I could bathe in this. You can make that funny. But it's not funny to, like, not have an opinion. But complaining, I think, leads to funny also. Like, I love going off of, like, something I've overheard, you know? Like, I. I find those, like, little moments to be some of the funniest things. Like, little chatter that you hear, conversations, you overhear, interactions, like, small interactions. You know? Like, I sometimes. Like, I had. I was just reminding someone of this the other day because people hit me up. Sometimes you have jokes that you go, whether you like them or not, sometimes no one ever brings them up again. And then sometimes people bring them up for years. And one of them was that I was checking into a hotel in Charlotte in North Carolina, and I. You know, when you check in, you say your last name. They're like, I'm, like, checking in Sagura. And the guy goes, oh, Japanese? And I go, yeah, 100%. And he goes, yeah, we don't get a lot of Japanese people here. And I'm like, what you do now? And he's like, yeah. He's like, yeah. Like, sometimes we get, like, French or, like, Spanish, but not Japanese. I'm like, I'm just like, look. I'm like, yeah. He goes. And he goes. I'm like, oh, yeah, you're saying it Japanese. Like, you can say. You can say Smith and it's Japanese. Like, I'm Sagura. It's not Japanese. And this guy was, like, dead. He was like, you're not Japanese. I'm like, do you have eyes? Like, you know, there's a look, right? And he's just like, oh, I didn't know. But it's like one of those, like, small interactions that I took to the stage and, like, I didn't know if an audience would respond to it, you know? And then they responded to it. But the funny thing is, like, it's now been close to, like, 10 years. And I walk down the street and people go, segura. Like, it's gonna yell it to me. One guy got a fucking tattoo of my face on his leg in a samurai outfit. And I was like, what? He goes, yeah, from that joke. I'm like, that's what you want to see on your thigh. Like, like, me as a Japanese warrior. And he's like, I just love that joke. Like, you have metal problems, dude.
A
Yeah, man. There's. There's. There's something. A lot of your jokes is about the. This, like, kind of awkwardness of conversation.
B
Yes.
A
Of you're really boring or you're just kind of not getting it. Like, one of your jokes. I forget what it is. It's like, yeah, you know. Where are you from? Seattle. No way.
B
Cool.
A
I got family in Denver.
B
Yes. You're like, yeah.
A
What?
B
Yeah, that was a guy.
A
Say that.
B
Why? Did you associate the two or the guy? I did one in a special, too, where I remember I was walking to this bank in la, and the guy goes. It was the security lobby guy. And so I just walk in, and it's like, there's the lobby area, and then you go into the actual bank. And just as, like, that courtesy thing, I go, how you doing? And he goes, well, I don't know, man. I haven't seen my sister in a while, but she's in Virginia. And I was like, what the fuck are you doing right now? And he told me, like, his whole life, like, the drama of his family. I was like, I'm going. I'm walking through the lobby.
A
It's just need a couple twenties.
B
Yeah. And he just, like, kept going on about, like, his family situation. I had to be like, yeah, okay. Thanks, man. But it's like. It is those, like, those small things that you go. Like, that antenna of yours goes up and goes like, oh, this is. This is funny to me. Because ultimately, I think in stand up, whether you're talking about Seinfeld or any comedian, like, what you're really doing is you're going, this is what I see. This is what I think is funny. And those, like, little interactions have always been something that I've reported. You know what I mean? Like, before I was on doing standup, I would have taken those interactions and told friends about them. I told family about, like, I was in the hotel and this guy did. I would have just would have told people because I find it very funny. Yeah.
A
Well, this is a way to think about it is it seems like there's the things that we all experience that we know that we all experience.
B
Yeah.
A
Like, we're conscious that we've experienced that it's raining outside today.
B
Right.
A
You know this. I know this. We both had that thought today.
B
Yeah.
A
But then there's the things that we all experience that we haven't had that conscious thought of, but everyone's kind of experienced.
B
Yeah.
A
Like, here's another example that I think has made for so many good jokes over the years is like, you land the airplane and then you get to the gate, and then the pilot does the ding and everyone stands up, and then you don't get off the airplane for like, 15 minutes.
B
Yeah.
A
It was one of those things I noticed probably 60, 70 times. Now all of a sudden, someone makes a joke about this, they nail it, and it's just hilarious.
B
It's hilarious. And you go, as a comedian, what happens is sometimes, oh, my God. It's one of the most unnerving things, is exactly what you're talking about. And you go, why didn't I just say it? You know what I mean? Like, you had the same observation, but you never articulated it. And then some other comedian does, and you're like, of course, of course. Like, we've all experienced this, but that person was the first one to actually say it. And sometimes you just go, like, yeah, like, I don't know. There's a disconnect happening from your brain that goes like, I don't. Don't. You don't have to say it. You know, and it's like you get a charge from hearing someone say it. You're like, yeah, I should be saying more. It's like the whole thing of, like, just say it all. One of my friends, I was talking to him because I put out a special a few months ago on Netflix called Teacher. Once you put out a special, you know, that material's done, so you got to start over again. Normally, I would go. I would take like, a couple weeks off and then start again. Right. But this time, it was the first time in my whole career where the special came out. And then I went right into pre production on my show on Bad Thoughts. And so I went into pre production, then we went into shooting it, and then we've been in post, and it's been like, a very demanding schedule. So I've never had this amount of time off from standup ever in 25 years. So I was talking to my friend, I was like, yeah, man, I've got to get back on stage and try new stuff. And I'm like, there's always this thing where it's a familiar feeling where you go, I have to start over again. How will I ever do it again? But you remind yourself that it happened every time. And I was like, yeah, I'm there right now. Where I'm like, how will I ever do this again? And his advice, Jeff Tate, great comic, he goes, just do them all. Even, like, write down all the thoughts, even the dumb ones, and take the dumb ones on stage. He goes, just say them all. And I was like, that's actually the best advice is like, don't try to filter through. That's not good enough. That's kind of.
A
The editor can't come too early.
B
No, just go. Just go say it. And when you. Because the thing that happens is when, like, you write down the dumb one and you go, that's not worth saying. When you get on stage, something happens between the idea and the performance where you will take it somewhere that you can't anticipate without an audience. The audience somehow manifests a different thing out of you that you go, oh, I wasn't even. I wasn't thinking this 30 seconds ago. But somehow being up here, the. The mixture of the pressure and the adrenaline and the thrill all comes together and something else comes out of your mouth, you know, and that's the part that's kind of, like, magical, that you can't really describe.
A
Yeah. How much do you think of good jokes being kind of about subtext and laying out the subtext?
B
It can be that where, like, you guys are going towards the same destination together or. Yeah. I think the most, like, the simplest way to describe, like. I think the best feeling of a joke always is the element of surprise. So it's almost like if they are anticipating, anticipating, and then you. You turn somewhere else. Like, you say the thing that they were not expecting that is the biggest rush or, like, the idea of upsetting them. Like, I like to upset them and then have them be, like, shaking their head, but you still manage to get them to laugh, so they're reluctantly laughing. That's also, like, such a rush because they're laughing against their own judgment. You know, which is also, like, very, very fun to be like, they're like, I don't like this topic, but damn it, like, you're making me laugh at it. That's always a fun thing to do.
A
And as a comic, you can put. Point that out. You're like, okay, there's clearly something here.
B
Yeah. Yeah.
A
You guys are holding back.
B
Yeah. You guys actually do like this. Like, you do think this is funny. Comics, we usually think of doing the hour in that way, too, where you. You build a good rapport with them as you're doing it. So a lot of times, I mean, some comics will open with, like, here's. I'm going to say something awful, right. And that's a. But usually, like, the most provocative thing is later in the set, because you've built this goodwill with them, right? Like, even in a. In a large, broad term of, like, minute 5 and 10 and 15, they're. They're just like. They're building trust. They're getting to know you. They're like, yeah, this is. I like this guy. And then minute 25, you can be like, here's the most awful thought. And they are. At that point, they're on your side. Yeah. So you kind of get away with more. So, like, he's doing that within that bit, but you also end up doing that kind of within your hour.
A
You know, like, at what levels do you think you want to land the jokes? You know, do you ever think, like, I got to get these words right? Cause sometimes I'll watch comics, and I'm like, it almost feels like you're reading a script that you had written in the past. It's, like, too refined.
B
Yeah. I mean, there's no substitute for doing tons of sets, Right. Like, when people, especially when it comes to, like, let's say, a taping, like, you kind of want to have, I think, a couple hundred runs of that set under your belt with a tape. Like, literally, like 200, 250, you know, where you're just like, this is a finished piece of work if you're not taping it. You know, part of that journey is, like, the sets that go wrong or the moments that you fall off track or. But I, like, I also don't even want to put a big show on sale if I don't feel like I've done all that work. The work is, like, that's kind of like what you remember, too, about it. Like, right now where I'm at this, like, beginning stage, it's. It's like, it's it's unnerving. You know, it's like you feel totally insecure, but you know that, like, little by little, you can do it. You know, you can do it. But I mean, it's also kind of the thrill because you go, like, what am I going to do? What am I going to say? And like, I, I started writing down just kind of like bullet point things. What about this? What about that? And so next week I go on stage to do like a 10 minute set. I have no idea how that 10 minute set will go. It could go terribly. I won't, I mean, I won't love that it goes terribly, but. But I understand that it's part of like the process of building. Yeah, but, yeah, if you're unprepared on a big set, it's, it's, it's one of the worst feelings here.
A
What is it that you love about Chris Rock's comedy?
B
He is the best at like deconstructing an idea. He has almost like this formula of like, say the thing, make the premise very clear and then break it down. High level comics break down concepts from multiple angles. They leave kind of like nothing there. They say the thing, then they go from this. So you're just like, you've exhausted it and you've done it. Like, he's, you know, like cutting and honest and brutal. People older than me, they're always like. So they'll be like, prior. You know, they talk about prior and I understand, you know, be a brilliant comedian. But there's also like the age in which you watch something, like the impact it has.
A
Kind of like music.
B
Kind of like music. Yeah, even also, like, honestly about sports, like, yes. People have, you know, the goat debate. Honestly, totally. Everyone who's like 35 and younger, they go, oh, it's LeBron. And it's like, yeah, you grew up
A
watching this, you never saw Jordan in the 90s.
B
For them, that's like, that's some old shit. And you're like, yeah, I know, but that's what I grew up watching, you know, so, like, the impact of it is different. So when I was like, I guess I was like a junior in high school, Bring the Pain came out. It's a perfect special. It's so high level, it just eviscerates every topic, like, just destroys. And so you're like, when you watch that, you're like, I remember watching that being like, I didn't even know someone could do that, like, do it like that. So he was such an influence on me. Like, I was so obsessed with his comedy that I have tapes of me doing standup in the early. Like, I'm just starting, and I am literally doing a bad Chris Rock impression. And at the time, you don't realize you're doing it when you watch it now, you'd be like, oh, like, I'm crouching, and I'm like, I have a hand like this, and I'm like. I'm literally like. I have his cadence and rhythm down. And you're like, oh, yeah. That's what new comics do, is you emulate your favorite comedian, you know, and. But, yeah, he is fantastic.
A
So I looked up some good Chris Rock jokes. So this from the 2000s, you know, the world is going crazy when the best rapper is a white guy, the best golfer is a black guy, the tallest guy in the NBA is Chinese, the Swiss hold the America's Cup. France is accusing the US of arrogance, Germany doesn't want to go to war, and the two most powerful men in America are named Bush and Dick. Need I say more?
B
It's clever. And it's also. You can see that, like, it's. It's so clean in that meaning, like, you're not, like. There's no vagueness to it. Like, Rock's thing is like. Like, really punches you with it. Right? There's no, like. Oh, there's some nuance to, like, what he's saying here. It's very direct.
A
Yeah, like this. If you can keep your son off the pipe and your daughter off the pole, you're ahead of the game.
B
Yeah. Yeah. Dude, that's so. It's so good. It's so good. Yeah. I mean, that's. He's. He's definitely one of the best ever. And I think.
A
Have you gotten to meet him?
B
Yeah, several times.
A
And what have you observed from what he does?
B
Well, the times that I've met him have all been, like, social situations, and he's been, like, super nice, like, super, super gracious. And I got to see. I saw him when he came to Austin, and I was backstage, like, hanging out and stuff, and. But, I mean, I was told, like, I. I had this thing, too, where I've always treated. If you're a guy and you're 10 years older than me or whatever, like, I can't talk to you like a peer, you know, I don't know if it's just, like, in how I was raised, but, like, I just can't.
A
Hello, Mr. Rock.
B
I mean, almost. Yeah. Like, and I. And I'm. And you could tell that, like, A number of these guys are like, just talk to me normal. And I'm like, yeah, I don't think, I don't think I can. So to me, it's like, I'm just, I'm just like a super fan in that regard with him and a bunch of guys from that generation. But I just, yeah, I just admire what they've done and like, they've inspired the hell out of me. Like, I really wanted to do it because of watching these guys, you know, and he's. Yeah, he's. He's absolutely one of the best. He's one of the best ever.
A
How would you break down the different kinds of comics? Like, there's the kind of Mitch Hedberg, one liner master. You're more of a story guy. How do you break down the different categories?
B
I don't think standup's ever been more popular. So what happens is the pool of how many types of community, how many communities there are is so much bigger than ever. Like, I, I feel that there used to be a time where I was like, yeah, I basically know the names of every working comedian. You know, like, it kind of felt like that. Like, I'm sure there was some that I didn't, but now it's, it's out of the stratosphere. Like, I, I have no. Like. And it's also internationally very popular. These. There's like super big successful comedians all over Europe, all over Africa, South America. Like, it's very, very popular now. And I think you can kind of. I mean, the categories. Storytelling is obviously one. Social commentary. Like, there's. There's the ones who are really adept at like, you know, would say like rock kind of falls into that, at least for part of what he does. Jon Stewart. But there's a bunch of them. And then there's the ones who are like, like content wise, it's about, let's say hypocrisy or, or then there's the ones who are like, it's all about relationships. But I think you basically break it down if you want to like not do so many categories. It's storytelling. It's almost like what you call like traditional American comedian, which is like a bit more like between pure joke writer and storyteller. So they kind of have that. And then there's like the pure joke writer. The person who goes like, clean setup joke, clean setup joke. Like, Dave Attell is like the quintessential joke writer. And then there's a, like Sam Morrell gets up there and it's just joke after joke after joke. Anthony Jesenik reminds me of that. So I feel like you could kind of be like, there's three. But then. Then someone brings up, what about, like, this, the, like, the alt type of comic where it's like, you're. You don't expect any of it. Doesn't seem like it fits into either of those categories.
A
You were talking earlier about having strong opinions. Brian Boltzmann is a guy, probably more than any comedian I've ever seen, who just comes at it in a way that I've never seen a comic come at it before. I've never met a woman who likes his comedy. Whenever. Whenever I go to the mothership and see it with girls, they universally cannot stand him. And then the guys are divided, about 70% of which I think he is. One of the funniest comments.
B
Yeah.
A
Makes you so uncomfortable. But then, like, heavy death metal, you kind of, like, open up to it.
B
Yeah. He also does that thing, too, where he. He's using how he knows people feel about a topic to his advantage. Yeah. You know, he's like, I know that this is an unsavory thing to say as a statement. So, like, the statement comes first, and you go like, that can't be your statement. Right. And then you follow it up with jokes. So it's like. It's. It's like, why I always thought it was so, like, it's so lame to be like, you can't say anything. You know when people are like, you can't say anything. And you're like, hey, you can. What are you talking about? And if you feel like. Yeah, but people are upset when I say that. You're like, right. That's an advantage. You know that they don't like that. So you can say it, know that they don't like it, and then follow it up with your jokes to support it. Like, to support your what? Even if it's not really your opinion, you're designing. You're crafting this thing based on the fact that, you know that's not a likable thing to say. Say. Right. And he. That's like. He has mastered that. He's mastered that. I know you're not going to like when I say this. I know you're going to react this way, but then I'm going to hit you with jokes that follow up on it to the point where you're just gonna either give in or be like, I'm leaving the room. Yeah. Yeah.
A
Where do you think you stand on this spectrum of, like, I'm a comic because I like me making people laugh, and I'm just all about that. And I would assume there's other comics who are like, I need to say what needs to be said.
B
I'm definitely not that.
A
Definitely not that.
B
No, no. I'm not that smart. And I don't have, like, this, man, I need to get this out of me into the world. No, I like. I like performing. I like doing stand up. I like making people laugh. I like to laugh. So to me, the whole thing is like, I just. I like doing stand. I like, it's. It's fun. It's. It's fun to do stand up. And I. You feel like this has been like the biggest thrill. There's no thrill, like, getting on stage with an idea you have and getting people to laugh. Like, that's the drug, that's the addiction. That's why you see comics perform into their 90s is because, like, it's a. It's a thrill. You want to just keep doing it. But I don't have, like, I need the world to hear this. Like, I'm not that guy.
A
Who do you think crushes stage presence? I saw Joey Diaz.
B
Yeah. Oh, my God.
A
Just gets up.
B
The tornado.
A
Tornado.
B
He's a tornado.
A
Unbelievable. Who have you looked at?
B
Oh, my God. Like, the perfect, if you want to call it stand up is somebody who has the combination of stage presence and the writing. Right. So they. Yeah, that. That's like, that's what makes a great stand up. But sometimes you watch somebody, you're like, this person's a great writer. Their presence is not as much. Sometimes people are more presence heavy and the writing's okay. And then sometimes it's like a combination of the two.
A
Yeah.
B
I mean, he takes over a stage and you're just like, oh, my God. It's just undeniable. You know, sometimes the presence is also what. What is exciting to you or what actually you realize you're responding to is how comfortable they are. Like, sometimes their presence is like power that's like its own thing where you're like, oh, my God. And there's. There's a number of people who come out like that. Like, they come out hot, you know, like, with energy. I'm trying to think, like, Leslie Jones kind of comes out like, okay, like you're. You're paying attention. You know, Dave, for instance, Chappelle, like, yes, he's very famous, obviously, but you realize even before he was super famous, it's this putting you at ease totally thing where you're like, oh, like, you don't feel, like, jumpy. You know, you're just like, oh, this person knows what they're doing. Which is, like, a huge advantage for that comedian, ultimately, is to put people at ease with, like, either your charisma or how comfortable you are on stage, you know? Like, I remember years ago. I don't know why, it's just popped in my head, but, like, I saw Gerard Carmichael. He was, like, 21 and he's black. So I was like, are you 40 or 12? I didn't know. But when he came on stage, I. Afterwards, I was like, I didn't know. I didn't really know him. I was just talking to him. I was like, how old are you? He was like, 21. I was like, you're 21? Because the way he walked on stage and the way he handled himself during this set, I was like, I would guess that you've been doing this for, like, 15 years, you know, and it was actually, like four or something, right? And I was like, that's crazy to have that level of comfort, you know, like, that's. I think, ultimately, I think the goal is you want to be on stage and you want to be a presence that makes people feel kind of, like, at ease, unless your thing is to be a tornado. But, like, for me, it's like, I want people to feel like, oh, he knows what he's doing. Because one of the things you notice about stage presence and the performing aspect over time is that good, seasoned performers on stage are not scared of silence. They use silence to their advantage. New comedians, scared, are terrified of silence. Like you. They're terrified. Literally terrified. Like, a few seconds have gone by and people aren't laughing, and they are literally, like, jittery, right? And they. And you'll start to see these different ways that they deal with that. Sometimes they get really loud, sometimes they get frantic. They're screaming. They're just trying to, like, get through the fact that this moment isn't getting laughs. The super seasoned people use, like, silence. And they realize that if they're. If they're not frantic and they're going. They're actually going somewhere with what they're saying, that the audience is slowly, like, leaning in. Yeah, they're leaning in. And then all of a sudden you realize, oh, look at everybody. Everybody is, like, watching this person like this. They're not. The audience is not going, where's the laughs? They're like, I'm following what you're doing. Because, I mean, Dave's, like, the extreme example where he's like an orator, he's a comedian, but he's a master at speaking to people and he uses that skill set in his comedy. Like he knows what he's got there and he does that thing or. I've been in arenas with him where there's 18,000 people in this arena and you can hear somebody's shoe move. I mean, that's incredible to watch. Incredible.
A
Craig Ferguson, the late night host who retired, he would get on and he'd just say, want to have an awkward silence, be totally silent. And he's like, oh, it's fine. And my sense is he probably did 20, 30, 40 of those, got comfortable with it, leans into the bit and it always ends up being funny.
B
He's so good.
A
He's so good.
B
He's so good at navigating, like, a moment where it's not working and making it work because he's. It really feels like he's just not scared, you know, Some of that too. Like, what I learned for myself about, like, getting on stage is because there's. There's you. You feel all the different emotions night to night. It's not like you're the same guy walking out every night. Right. Sometimes you're confident, sometimes you're overly confident, sometimes you're scared, sometimes you're nervous, sometimes you're angry. Like, you feel all these things. And I found that, like, the best mindset for me to go on stage with is silly.
A
Yeah.
B
When you feel when you're backstage and you're like, literally goofing off, like, like really around with your friends saying dumb, like dumb. Actual dumb jokes, and you guys are laughing and, like, really having genuine silly fun, and you take that energy on stage to me for what I do. That's the best way I can go on stage. And you can kind of manufacture. You try to manufacture it, you know, like, let's be silly, let's not, you know, but when it's really happening, those are the best sets. Totally the best sets.
A
Well, do you find that people can help you get into that? Like, for me, I can't be like, if you were like, okay, Tom, David, be silly. No, I just can't do that. My sister walks in the room right now.
B
Yeah.
A
You will see a silly come out of me that I just cannot create, and it'll happen in five seconds.
B
And like, if you were a touring comedian, what I would tell you is, like, bring your sister on tour. Yeah. No, for real. Because you end up constructing these. Like. Like, when I go on tour, I have a tour manager, tour coordinator, production manager, security, merch person, photographer, opening acts. Like, all these people, and they go city to city to city with you. It's so. It's so important that you have. You have to be, like, especially silly with them. But you go like, you want to feel comfortable with your crew. And, like, I feel like when we are in a good place, we are kind of laughing, joking about, like, look at this guy working here, this lunatic. It's like, you know, we start having those conversations, and you. You take that, you're backstage doing that, and then they announce you, and you're taking that energy on stage. It's much better energy to hit the stage with than, like, down or, like, super serious.
A
Need to nail it tonight.
B
Yeah, no, you don't want to. Like, you don't want to hit the stage. Like, I don't think like that now.
A
Yeah, you don't really strike me as a one weird trick kind of guy. But are there things that you go for? Like, this thing tends to be pretty funny. That thing tends to be pretty funny. For example, I don't know, mall cops, 5 out of 10 authority, but they treat it like they have 10 out of 10 authority.
B
Oh, yeah? Yeah.
A
Like they work for the IDF or something. Always funny.
B
Yeah, I mean, it is always funny. You're right. Like, the. The people who want to exercise, like, the little bit of power they have. But you. You see it, and you're like, I see what's going on here. Even tsa, you realize that, like, that this guy, this TSA person who is like, give me your id. Stand here. Sometimes they are really flexing on it. Like, are you, like, a corrections officer? Like, what do you. Who do you think you're talking to? Like, I had one. One time that straight up, like, tried to embarrass me in. In security, like, at the line. She's like, you got in the wrong line. And I'm like, okay. She's like, does this. Do you not read your past? And I'm like, what do you think you're doing right now? And you could tell this guy was like. He was like, hey, hey. A guy I don't know was like, chill, like, you don't want to get in trouble. I'm like, I'm not worried about this person. Like, this is a TSA agent. She's a glorified mall cop. If you're gonna flex on me like you're a special agent, you know? Like, I'm. I'm not. Like, I mean, I. I called over this person's supervisor.
A
Yeah.
B
I was like, you gotta retrain this morning.
A
Same thing with bouncers at a middling ball.
B
It's exactly the same thing. It's exactly the same thing where they're just like. What happens is somebody who has no power in the world, and then you go like, this is the one. These. These three square meters are yours to be the most powerful person. And then who that person is comes out, you know, in their dominion. Yeah, that's exactly what it is, man. It's just like, you know, it's like crossing the street slowly when cars are coming. You're like, I'm a show everybody that I get. Like, yeah, you can get hit by a fucking car, too, man. But, yeah, like, these. It's the TSA ones of all are like. I mean, I'm sure it's not the most thrilling thing to do all day, but when they. When. When they flex on you, it's. It's definitely some. It spins me out, dude. It spins me. It's small. It's mall cop energy.
A
It's mall cop energy.
B
Yeah. I mean, the other thing, too is, like, as. The longer you do this, you know, it's like you start. You start, like, going like, oh, I have a take on whatever. Like, AI, right? And then you go to the club that night, and you see, like, 15 people doing AI bits, and you go, okay, I'm gonna do mine if I feel like it is like the. I think the rule is, like, if you feel like your. Your bit is far superior to these other ones, than you do it otherwise. It's what led me to doing so much storytelling about life, because you go, it's my own, you know, it's my life. So that's why it's like, stuff with my kids, stuff with my mom, stuff with friends. Like, you start telling these stories because you realize no one else has that story. No one else has that perspective. It really comes from the fact that, like, I've always loved storytelling, but I also know this is not happening to anybody else. Right. In my way.
A
Or it is. And you're just seeing it. Like the in and out burger bit where they humiliate you with eating in the car.
B
Yeah. They're like, are you fat? Do you want to eat in your car like a fat boy? And you're like, yes. And they give you an open pig trough. Eat out of that. Yeah. And you're like, okay. Because I almost feel like when they go, are you going to be eating in the car? You're like, Hell, I'm not a fucking loser. Never do that. And then they go, you know, you want to eat in the car? Like, yeah, I kind of do. Yeah. It is one of those things where I feel like when you have observations like that, like the in and out one, to be specific, you're like, I got to get this out there because someone else is going to, you know, I mean, that's one of those. You're like, someone's going to say this. Somebody going to say this. So I got to. I got to do it. Yeah. Because you know that, like, other people have to be. Are clearly experiencing this, too. I remember, too, sometimes you're on tour and, like, even with that bit, I would be doing it and, like, it would be clicking with audiences, right. And you're like, man, I got to get this special out. Because, like, that someone's going to do that bit, you know, like, you feel this, like, almost relief that you got it out, because some of those things feel like someone has to be making this observation too. You know, you feel, like, this almost, like, urgency to get it out. Yeah.
A
You got me thinking a lot about the connection between. I'm frustrated with this thing that a lot of people get frustrated with. And then. What's the joke here? Yeah, the thing that has frustrated me to no end is. Is how every opener at a concert just sucks.
B
Do they all suck?
A
I mean, in my experience, they're just. Maybe that's too harsh. Concert openers are just terrible.
B
It's one of those things where, like we were saying, complaining is part of what's funny, you know? So, like, you making that observation to me is like, yeah, stick in that. Like, keep talking about how bad it usually is, that that's where the joke. In other words, the joke is you're on the path to what you're. Whatever the joke is there. Right? You're on the path. And it's like, you know, there's the. Sometimes the thing that's too obvious isn't the joke because you're like, it's too obvious. You digging in on the feeling of what's bothering you is where the joke lies. As long as you keep expanding on it, the joke is in expanding on why you know, why it upsets you. So it's like, is. Is what upsets you that you're wasting time? Does it upset you that you showed up early? Like, what is it that upsets you? The joke is in there. You have to, like, keep digging in. Yeah. Didn't you think, just show up later, but then You.
A
If you miss the main thing, whole night's ruin.
B
But if the. If the show starts at 8 and you know the main act's not going on till 9.
A
No. Till 11, I'm not showing up till 10:30.
B
Oh, okay. And even that 30 minutes bothers me. Bullshit.
A
Yeah, of course it bothers me.
B
See, there's. The joke is almost in there that you're bothered by hardly any time. That's what's funny, is that you're not spending three hours watching some bullshit. You're spending, like, 15 minutes, and you're fucking annoyed. That's what's funny to me. Like, dude, what are you talking about? You can't sit through 15 minutes of some shit. It's like somebody yelling at the trailer before the movie. You're like, bro, just eat some popcorn. What is your problem?
A
How do you feel like. Okay, let's take this joke. So how do you feel like you're able to tell a joke? In Bad Thoughts, TV show versus stand up. Like, what do the different mediums afford you?
B
Oh, my God. It's so dramatically different and so fun. Yeah, it's so fun because, like, in. In standup, you know, it's like, here's a thought, here's an observation, or here's something that happened, and you paint your picture with words. You tell it. And like I said, there's. There's no thrill, like, the live audience reaction to it. But in Bad Thoughts, when the writers room starts, I'll come in with, like, a few drafts and will read it in the room. But you're there with other comedy writers, so it's so exciting because this is something you don't do in standup. You don't go, like, here's my stuff. I'm saying I'm gonna sit with, like, six comedians and go, like, what does everybody think? Like, you know, right? Sometimes they'll tell you, like, I think this, or they'll give you a tag. You should say that at the end. You're like, oh, that's a good idea. But it's not a fully collaborative process. But a writer's room, it's so much fun because you're sitting with, like, these other comedy minds and you're hearing things from all different angles, and you're like. It just becomes like, oh, my God. Yeah, I didn't. I didn't think of it like that. And you. Sometimes I'll go, and I want to tell this story, and I think, this is how to do it. And one of these people will, like, either find A hole in the story aspect, or they'll bring up something else that makes your mind. Like, that's the biggest thing about a writer's room, that people. I don't know if people know is that, yes, sometimes I can go, here's an idea, and somebody goes, I have a take on it, and they'll take it somewhere else. But sometimes it's that I say something, the other writer has something that they say, and it sparks your own idea, which feels so exciting. You realize without them having said something, your mind would not have gone to this other place. Right. And that's like this really exciting thing. It's like you get to do specifically with bad thoughts. We get to do, like, mini movies. Like, they're like little crazy short films. And the fact that you get to, like, come up with this concept, paint a real picture, have it shot like cinema. Like, we have, like, really cinematic look. And then you get to bring in other actors that just elevate the whole thing. It is so. So it's like one of the most fun experiences that I've ever had.
A
What kind of TV did you look at in the same way that you looked at Chris Rock? And you're like, I like that. I like that. I want to incorporate this. Wow. They're really inspiring me.
B
From the early onset, I would say, you know, I grew up in the era of, like, a lot of sitcoms, so I did watch, like, Seinfeld and Cheers and Roseanne and just like so many of those shows. Then I got into more dramas. Like, you know, they kind of got so much better. I feel like as I was getting the Sopranos and you're Breaking Bad and. And. And these types of shows where you're like, oh, my God, this is, like, so great. When we were, like, taking bad thoughts out, like, pitching it. Yeah, I actually funded a. I made the pilot so I didn't have to, like, pitch the idea. I was like, here it is. One of the lines we would say was like, oh, this is like black mirror, but fucked up comedy version. What I loved about that show is they take these ideas and they obviously they twist and turn, but they also make you fall into this world and they. They make it very cinematic. Like, to me, like, the way it looks is a huge factor in the show. You know, it's like, you really want to have that. But the fun thing about bad thoughts is, like, they also. Netflix just goes like, yeah, dude, make what you want to make. Like, do your thing. And they give us thoughts. You know, like, they go, leave what if you did this? Or what if you, you know, you lean more on this, but they don't go like, you can't do that.
A
Well, I was thinking as. As I was asking that question about what you can get at and stand up versus a sitcom. I think that the ability to kind of act something out and then take something small and make it a little bit more ridiculous.
B
Yes.
A
Will, just.
B
My favorite one from this season is that. Tell me about the new season. It's. It came from. It's one of my favorites, I should say. It came from an idea where I was sitting. I was sitting after a show in the van, like, they were driving us from the venue to, like, the hotel. And I had Kirk Fox, who's a comedian and actor. We were like, wouldn't it be really funny if a comedian for Merch had something unconventional and ridiculous to sell? That was like. That was, like, inconvenient to sell for both the seller and the buyer. And we were in the van laughing so hard, like, little tears, like, doubled over. And we just kept riffing on it. And I laughed so hard that I was like, all right, I'm writing this. I'm gonna take our make believe hypothetical thing and write a draft of it. So I wrote a draft and I brought it to the writers room, and people were like, this. This is insane. You know, like, this is good insane or bad? Like, no, like, they were like, this is funny. But like. And I go, no, no, we play it like, this is the most sincere thing, which is the most fun thing to do, is to take an absurd idea and really play it seriously. And there's moments like that in the writer's room where you're like, are we doing this one or are we not? Because you end up having more ideas than you can shoot. And I kept putting it on the side of the board that was like, we're doing this. Sometimes people would move it over here and we'd bring it back, and we ended up doing it. And it still makes me laugh. Almost like it did that first day that it's so fun to be able to take this thing that you said hypothetical and actually put it on screen as like, this is a real thing. That's like, to me, the equivalent in standup of like, here's an idea. I'm taking it on stage. And you're like, oh, my God, what a thrill that I got to say it on stage. In Bad Thoughts, you can have these, like, silly ideas and actually shoot the scene with the dialogue and the setting and, like, make it a thing. And that one really makes me laugh so hard.
A
I love when a bit.
B
Yeah.
A
Gets in your head and then you start seeing it all over the place. Because then that bit kind of lives with you. Yeah, that's what's so fun about a skit.
B
Yeah.
A
Or sketch. You can just bring it to life.
B
Yes.
A
And it's like the perfect amount of exaggeration where. How do you exaggerate enough where it's, you know, funny and sort of absurd while also retaining the reality of the situation of like, this is a thing that could happen in your life and probably has.
B
Yeah. Well, to me, like, the formula for like, taking those ideas and putting it on screen like that is like the, the, the emphasis of this is grounded and real. And like, one of the things we would do, like in casting is sometimes you'd look at the list of potential actors and you have these great comedy actors and then you'd have the dramatic actors and you go get the dramatic person. Get the dramatic person to deliver this thing because it gives it weight, it grounds it, it makes it real. And the more ridiculous it is, the less I would want the comedy person. I want the drama person. And that is like, the most fun, is taking the craziest idea and making it, like, seem like you're doing Shakespeare or something. You know what I mean? But, yeah, that's the most fun.
A
It's like, funnier if it's not. If they're not trying to be funny.
B
That's the key to it all. The key to that all is like, that's funny if both of them are playing it super real. And the big thing that makes it funnier is that the longer you hold on, the real amount of time, it's funnier. There's a. The same way that, like, comedians get nervous. I said, like, with silence. There's a lot of things about, like, television and film today where people have like, these. They're like, you'll notice.
A
Fast, fast, fast.
B
Edits just happen so much. Right. Like, even if you watch like, European films versus, like, let's say most American studio films. American studio films have an edit like every three seconds. And then sometimes you'll watch a European film where the guy making coffee, it'll be like a one shot and he'll. It'll show him, like, putting the water into the thing and like, you're watching the whole thing fill up and then he, you know, presses the button and you watch. But what you realize is you're like, oh, I'm not anxious watching this I'm watching somebody make coffee. Like, that's how it's right. It's real. The comedy of that moment relies on you actually having the time where the guy's like, waiting. The waiting is like, it makes it feel like it's real. And then you're like, God, so much. That's so fucking long. You just got to hold that thing. But you want to sit in that. The real tension of a 25 second door, you know, which is like so long to watch. But you're like, that's why, that's why it's funny is like, it's. If she doesn't, you know, like, try to make it funny or, you know, if he doesn't do this, it becomes funnier because it's real. The realness of it is what's funny.
A
When you're telling stories on stage and whatnot, what have you learned about setting the premise?
B
I mean, one of the big things about the people always talk about when you're doing standup is like, sometimes you have a story, you go, but what's my way in? Because it's almost like your reason for telling the story is as important, if not more so, than the story itself. Because it gives it weight. It gives it like, people go, oh, this is a story. Yeah, it's funny. But the reason for telling it is just as important. That's where a lot of. That's where like when you talk about, like the work of, I think doing standup, part of it is like, I gotta figure out things like that. That becomes the puzzle. Why am, why am I telling this story? Am I just saying, like, this thing happened? You can. And maybe it's funny. Like, for instance, I told the story on my last special of when I almost, when I booked the. To be the spokesman for Subway, like years ago, right? I booked and. And I was doing it with Jared from Subway. And I tell the whole story. Now you can just go one time. I was almost the spokesman for Subway. Here's what, like, tell the story right. You could tell that story. But on stage, what I did was I would start by saying, I'm so grateful to be performing here, like doing this show. I never thought this was in the cards for me, like being able to do arenas and amphitheaters and like huge theaters. Like, I thought the highlight of my career was, was when I booked the spokes, the campaign to be the spokesman for Subway. So right there you're having. You gave yourself a reason to tell the story. It's different than just saying, I was almost a spokesman for Subway one time, you know, because then they go, oh, like, that's cool. But if you're connecting it to, like, this is cra. I can't believe I'm on this stage. I'm super thankful for being here. I never thought this would happen. I really thought the highlight of my career was many years ago when I broke this. Now you have a reason for telling the story. They're engaged before you started. And I feel like that is a lot of the work, especially for storytelling, is, yeah, you have a story, but figure out your way in. Figure out a reason for saying it, even if it's something like. Like that. But you. You want to dig and not get lazy. Right about those moments. You want to figure out why.
A
Well, I'll talk to a lot of storytellers on how I write, and they'll say something similar, which is, you want to set the stakes to show people why what you're doing is important. But a lot of the art to the more baseline stories is making those stakes clear. So, for example, if I were to say to you, man, my apartment was a mess. My apartment was a mess. It smelled like weed, you'd be like, okay, that's fine. That happens to a bunch of single guys or whatever. Now, if you were to say, I just moved to New York, my parents a little worried about me. We fought a lot about the move to New York. This was their first time visiting, and I wanted to show them that I'm a real adult now. This was the right decision.
B
Yeah.
A
Now they're visiting. They just text me, hey, we're here to surprise you. We've just landed at Newark. We'll be there in two hours. Yeah, my place is a mess.
B
Smells like.
A
Smells like weed.
B
Yeah.
A
Whole different scenario.
B
That's exactly right. Yeah, You've. You've created stakes, the pressure. Now the audience listening knows, like, oh, there. There's. You could really disappoint them. The story, the stage version of that is like, what's your way in? Right. That's what. That's how we would describe it is like. You could say, my place is dirty, smells like weed. My parents aren't gonna like it. And people be like, yeah, I get that. But if you tell them the backstory part and then you get to that, it becomes a lot more. You have your reason. Like, you. What's the reason for the story? So that's what I spend. I try to spend time figuring out sometimes, like, what is the. And then, you know when you get it wrong, you're like, oh, I just, I didn't. I just told that story. I just said like, blah, blah, blah. And it may, it gets laughs, but you realize that if you had done the work to setting it up, people would be more into the story.
A
When I think of jokes, I think of punchlines. But do you think of punchlines a lot?
B
I think the, the way you do, like, like storytelling is the first time you do it, you go, just tell the super long version of it. Okay? Like, don't, don't go into it with like, it's gotta be like this. And you realize the story is fat, right? Let's say it's like a seven minute story or something. Seven, ten, whatever it is. Then you begin the edit process of like, you don't need this information. You don't need this now you have it tighter. And then you go in and go, I need something here, I need something here. I need something here. Which is like kind of putting in jokes and punchlines throughout. Ultimately, you love to end one of those on a big punchline. And that, in a way, it's more rewarding when you solve it because sometimes you go, I know there's something there. I know there's something there. And then you. One day you get it. But there's also like something that's like, soothing and pleasing about the ones that you're like, yeah, I just went on stage the next day and just said this stuff. And it all worked. And it all worked with, like, tension, rhythm, punch lines. Like, it just all came together.
A
So what does a set list look like?
B
It's just worth, like, one word for each thing.
A
Augusta Mansell. Blackout drunk. Hitler.
B
Yeah.
A
Duck.
B
Yeah, yeah, the Hitler thing. I was just fascinated. Like, I was fascinated because I watched a documentary and when I watched the documentary, there was like, all these details about, like, his drug use. And like, everybody feels like they who has any knowledge of World War II understands that, like, the Germans had like, methamphetamines. But in the documentary they were like, yeah, a lot of people don't know that he was on cocaine. He was doing cocaine also, and it was given to him in the mornings by his personal doctor. So I was like, you know, I would. I just went on about, like, how like, that things make more sense. Like, you know, like, you know, he'd wake up in the morning and that his doctor was just like, yeah, like, good morning. My fuel. And just gave it to him and that he would just do a rail and be like, juice and be like, Jesus Christ, like, Like, you know, I mean, like, if you have a heart full of hatred and cocaine, like, it's not a good formula, right? Like that. So we just, like, talk about that and, like, how his coke out behavior makes sense. Like, he'd be like, you know, like, you guys, like, my new. I shaves the sides off my, like, the beat out showing his stash. Like, you guys want to see my art? You know, like, just ranting and raving. But that's one of those things where, like, that's one of those jokes where you feel like you literally watch a thing, talk about it on stage, and you're like, oh, there's a bit, you know, like that. That whole idea of, like, are you turning it on or off? It's like you just talk about things that enter your mind, right? And then I also talk about, like, my kids. So those are just like, I'm gonna talk about literally what happened and the kid. You know, audiences will tell you what is, what's the bit and what isn't. But it's just, I report sometimes people go like, oh, I know, I know you made that up about your kids. I'm like, I don't make up a single thing about those guys. I don't make a. There's no invented thing about. You're literally, if you have kids, you'd be like, you know, you're like, yeah, dude, this is. This is really what happens. Like, my kid yanked a duck out of a pond by its neck. And he was like, can we take this home? And I was like, you out of your mind? Like, I just told that, like, the whole story of it. And people. People with kids go like, yeah, dude, especially with boys. They're like, yeah, I get it.
A
How much do you think about word choice? Like, yanked is a way funnier way to say that than my kid pulled a thousand percent.
B
You. Sometimes you're. It's one of those things you're heavily conscious of when you're in the mindset of, like, what. When you're thinking, like, what is funnier? Because you're. There's words and sounds that are. Yeah. Funnier.
A
It's just Yiddish things are just universally hilarious, dude.
B
It's like when somebody goes like, somebody got hit by a car. Somebody got, like, clipped by, like. It's like the. The clip is a funnier word than hit. You know, there's all these like, little. Little things that. Yeah. You start thinking about. And when you. When you're really, like, dialed in on the version that is the funniest, you That's. That's also part of the work. Sometimes you're, like, also sitting around talking with people and, like, especially offstage conversations where you. You. There's just funny people who describe things in a funny way, and you're like, oh, that's how to say that. You know, like, the guy didn't get a hand job. He got it. He got tugged. It's like, that's funnier. You know, all these. That your ears just kind of pick up on. You're like, that's definitely funnier to say that. Yeah.
A
How did you realize that accents and sort of merging into other languages real quick was so funny? Because, like, you do that with Spanish.
B
Oh, it's all the time. Yeah. I mean, from when you're a kid, you realize that an accent is. It's hilarious. Accents are hilarious. Hilarious. So I've always loved languages. Like, love languages. I love learning about languages. I. I'm on my phone doing, like, you're a duolingo guy language. I do, like, three of the apps. Really? Yeah, I do them all the time. I just. I've always liked languages. And there's something about people pronouncing things that's just funny. It also paints a picture if you're like, I was. I was in the. I don't know, I was in the store. And the first one was like, are you looking for something? It. It's different when you're painting a picture of a story versus somebody being like, are you looking for something? Like, you imagine a different person. Right. It adds color to the story. So. Yeah. I mean, doing accents and voices is, like, I think a huge part of. Of making it funny. It's. It's. Yeah. I mean, I talk about my mother all the time who, like me. And her accent is strong, you know, like, she's Peru. She's from Peru. Yeah. Yeah. She's still Howard Jew. And I'm like, jesus, I'm Catholic. You know, She's. Yeah, she's a very strong accent. There's that hilarious Hilaria Baldwin thing where it went viral.
A
No. What was this?
B
She's American, but she, I guess, spent a lot of time in Spain growing up.
A
Okay.
B
She's America. She's, like, from Boston or something. And she was doing some interview where she was like. They were like. I think it was for, like, a recipe. And she was like. They were like, how do you make this thing? You know? This is like Alec Baldwin's wife, I think. Right. And she was like, you know, you slice the tomatoes and then. And Then you slice up. How do you say in English? Cucumber? How you say it in English. Like, that's your first language. What are you talking about? You know how to say it in English. How you say. She didn't say. How do you say that? She goes, how you say in English. Like, she transported. Teleported to this other Spanish, only speaking. It was. It was insane. And I. I roasted her so hard. And then. And then this thing happened to me where I was like, there's always just, like, this karma of how this works, because you. What I forgot was if you are bilingual or trilo, whatever, and you start speaking one of those languages a lot, let's say the second one, Spanish, and you're immersed for a period of time, you literally do run into going like, wait, what's the word again? Like, of your native language. Wow. And it happened to me where I roasted her so hard, and then I went on a South America tour. So I was like, in Argentina, and then I was in Chile and Peru and Mexico City and one of those airports. Somebody came up to me and was like, hey, will you sign this? He's like, yeah, yeah. But I've been speaking just Spanish 24 hours a day for, like, I don't know, a couple weeks or something. And they were like. They gave me the pen, and I was like, oh, what's. What's the name? And they're like, oh, yeah, it signed to my son, you know, August or something. And I was like, okay. I was like, august. And I put the comma. And I was like, how you say in English, like, I wish you well? Like, I couldn't think of the words because my brain was. And I was like, oh, I'm a for. I was like, this really does happen. Like, if you are immersed enough, you'll forget basic words. You know, it was just one of those things where I was like. I had to go on, like, a podcast and be like, sorry, Floria. It happened to me, too. Sorry. I guess it is a real thing. Yeah.
A
When you. What have you learned about opening bits? Like, walking out, first thing you say, that's a great.
B
It's a great. I have done every version of how you can open. And what I mean is, I've done the slow burn where you walk out and you're like, how's it going? You know, like, I'm gonna just take my time getting into, like, the show aspect of this. I've done hard. Hardest joke I can think of right out of the gate. And I've done everything in the middle. I think there's valid points and advantages to doing each one. Ultimately, I think opening on a strong joke is the best way to go. Having done it all and, like, you could ask me on a different night where I might be like, no, I want to do this other way tonight. I think it's all fine. Like, it's all supposed to be experimental and fun and trying things, but if I had to, like, go like, you can. You should do it one way. I think you owe it on a hard joke. Yeah.
A
I'm amazed, watching your sets, thinking about even dinner conversations, how funny callbacks are. Obviously, you're sharing information, but you're also kind of creating a world. And there's something about calling back to something in the world that you've established.
B
Callbacks are fantastic. What you get kind of aware of and don't want to fall into is, like, the overdoing it.
A
Yeah.
B
You know, like, anything. Like, anything. Exactly. But there's, like, comics who is just, like, callback, callback, call back. You know, I mean, like, where you're like, no, no. But when you're cleverly placing them and not over, like, the. The fine line of, like, the perfect amount of them. Yeah. I mean, you also see how much a live audience, like, love. It's also like in. In conversation, when you do a callback to, like, it just shows the person that, like, you're paying attention. Right. It becomes, like, kind of charming and smart. It's like, oh, this person's witty. They remembered what we said five minutes ago. Like, it's that kind of thing. But then you do that in the. In the presentation of an hour, having a few carefully placed ones. Yeah. It's like, it's fun. It shows, like, that you're thoughtful. And I think audiences, when they're dialed in on it, they love it. They love it.
A
Well, it gets to this deeper point about comedy that the line between extremely funny and extremely annoying is actually pretty thin. Like, we all had that friend growing up who they would make a joke, and then they'd be like, oh, my God, that's funny. And then they would never stop making the joke.
B
Yeah. Try having kids.
A
Yeah.
B
That's what kids. Because kids don't realize, like, the first time they make you really laugh, you can see in their eyes or, like, they're like, what's going on? And you're like. You're telling them, like, what did you say? And they say it, and you keep laughing, and they're like, you realize it's exciting to them. They're like, oh, I can. I can have this effect on someone. It's. It's gotta be like this. It's a new sensation to them. Like, I'm. I can say something. And somebody doubles over laughing, and then they inevitably say it like 3,500 times. And then you have to be like, hey, man, that's not funny anymore. And they're like, wait, why? You're like, because you said it too much. Like, you just. You're saying it way too much. And yet that can happen in with adults and with comedians too, of like just the same point over and over and over, and it's. It loses. That's why I think, like, the key element to all of what is funny is surprise. Like, you want to be surprised. Ultimately, you laugh the hardest when you didn't expect. Catches you off guard. Even whether it's a kid at the house or somebody that msg, it's like you want unexpected thing to be said. Yeah.
A
As you were writing your book, what was different about that kind of comedy versus the show and stand up?
B
The book was really one of the most rewarding and challenging experiences to me. And it's. It's not that deep of a book. But. But I wrote like, a lot of just stories from. From life. And what I found was, like, having a great editor, publisher was that like, standup's all alone, television and movies. It's like huge collaborative thing. The book writing is a. It's a dance. It's like a marriage. It's just the two of you. And that. That was like the. Because I had. I had no idea what I was doing. So I would just write pages, send them in, and I did. I wouldn't know. Sometimes that was the thing is, like, it was never the same. Like, one chapter I would get back and she would write, this is perfect. This is what the book should be. And you're like, fuck, yeah, let's go. You're like. You're like feeling yourself, and then you, like, see the next thing. She's like, crossed out. What is this? Need humor here? This doesn't connect to this. And you're like, what the fuck? And it felt like a math problem, you know, like. Like a puzzle you had to solve. But it goes back to, like, then I wanted to solve. Like, I'd be like, no, I like this story. I like the world. But she's right. Like, she was just brilliant. So she's right. I gotta readdress this. So I liked the challenge of it. I found it to be really a Lot of work, man. Like, even for, like, it not being this, it's not a 400 page book. I was like, man, this is a lot, lot. It's, it takes a lot. You really have to love that process to do it. As soon as, like, it came out and it performed fairly well, they were like, you want to write another book? I was like, no. Like, this is so much goddamn work. I, I, it's not that I would never do it again. I would. But I remember at the time, I was like, you gotta, I need a break from this. And I couldn't believe really how much goes. It made me appreciate, like, the authors that do it for a living all the time, so much more. Having had the experience of doing it, it was a, it was a lot. It was a lot.
A
Yeah. One of the things that I think you said about it was you just didn't have other things to lean on. Pacing, rhythm, diction, whatever else. It's, it's like all you got is word.
B
It's the most, I'll tell you this, it was the most exposed and vulnerable I've ever felt in, in any art form. Because as a standup, I know I can say something, but I know I control so much with my delivery, with my cadence, with the way I say it, with my facial expressions. You have all this power in doing that. When you are actually like, hey, I wrote this. And handing over the pages, you go through this absolute, like, crippling anxiety of like, does any of that translate the way that I intended it to be? Like, I'm not controlling the cadence anymore. It's the written word. So you feel like this, like, part of you is like someone going to be like, what the fuck is this? Like that that's how you feel when you hand it over and you're just kind of like waiting for them to be like, yeah, this is, this is funny. And you're like, oh, my God, I didn't know you think part of it.
A
So you're used to instant feedback, a thousand percent.
B
And that waiting of like, yeah, we'll get back to you in a week. You're like, it could take a week. Can you imagine, like, stay standing on stage and be like, let me know how this goes next week. Like, you know, you have immediate response. And it was, yeah, that was some of the most anxious I've ever been. And I, it was that part of like, I don't know if you're reading the words the way I wrote them in. Stand up, I know that I'm saying it this way, and I know how it's landing. And that difference to me between the two was so massive that, yeah, it was like. It was terrifying. It was actually terrifying. But I ultimately a super rewarding experience. I'm really glad that I did it.
A
It's great to meet you, man.
B
Yeah, you too, man.
A
That's fun.
B
Thanks so much.
A
Yeah.
Host: David Perell
Guest: Tom Segura
Air Date: May 20, 2026
In this episode, David Perell is joined by stand-up comedian, podcaster, and TV creator Tom Segura (known for his Netflix specials and the show Bad Thoughts). The conversation dives deep into Segura’s approach to observational and story-based comedy, the writing and revision process behind jokes, the power of subtext and surprise, and how comedic sensibilities translate across stand-up, television, and writing a book. Along the way, Segura offers practical advice, hilarious anecdotes, and candid reflections on the “meta-mechanics” of creating comedy from start to finish.
Observation as a Habit
Irritation and Humor
Everyday awkwardness and mundane conversations can be comedic fodder.
Notable Quote:
Comedy often emerges from articulating observations everyone has but few have voiced out loud (e.g., people standing immediately after a plane lands and waiting unnecessarily).
Advice from Jeff Tate: “Just do them all. Even, like, write down all the thoughts, even the dumb ones, and take the dumb ones on stage. ... Just say them all.” (09:53)
The stage is where ideas are tested and often transformed; audience response and the adrenaline of performance can change a joke’s direction or delivery in real time.
Editing vs. Output: Don’t let the internal editor come too early; getting every idea out there is critical.
The best jokes deliver surprise—audiences follow along with a premise and are caught off guard by the punchline, sometimes laughing against their judgment.
Building rapport allows deeper, edgier jokes to land; a comedian might “save” provocative material for later in a set when audience trust is established.
Hundreds of Runs: For a taping or special, Segura does 200+ sets to refine the material.
The Thrill and Terror: The process is always unnerving at first—starting over, testing material—no matter how experienced.
Chris Rock’s Impact:
Comic Archetypes:
Having an opinion—any opinion, whether positive or negative—is crucial.
Comics can use their awareness of taboo or “unlikable” statements to drive the audience into discomfort, then win them over with jokes.
Segura leans toward “making people laugh,” not driven by a compulsion to change the world or deliver moral messages.
The best sets come from being in a genuinely silly mood backstage, often with friends or crew, and carrying that energy onstage.
Surrounding yourself with the right people backstage helps foster this energy.
On Recognizing Jokes in Conversation:
“It’s kind of like the muscle... the biggest muscle of it all, I think is recognizing, oh, that’s something. Versus I’m just kind of shooting the shit.” — Tom Segura (01:40)
On Annoyance and Comedy:
“Being annoyed is funny. My seven-year-old’s annoyed all the time and he’s hilarious.” (Tom, 02:12)
On Indifference:
“What’s not funny is total indifference.” (Tom, 02:47)
On the Importance of Having Opinions:
“It’s not funny to be like, it’s fine. I don’t care. That’s not funny. It’s funny if you go, this tastes like somebody into a cup and boiled it.” (Tom, 02:50)
On Stand-Up vs. TV Writing Rooms:
“In standup... you paint your picture with words.... But a writer’s room, it’s so much fun... sometimes I say something, the other writer has something, and it sparks your own idea, which feels so exciting.” (Tom, 39:13–41:46)
On Stage Presence:
“One of the things you notice about stage presence and the performing aspect over time is that good, seasoned performers on stage are not scared of silence. They use silence to their advantage.” (Tom, 27:10)
On Overuse and Surprise:
“That can happen with adults and comedians too: just the same point over and over... it loses [its effect]. That’s why ... the key element to all of what is funny is surprise.” (Tom, 66:42)
Stand-Up:
TV/Writer’s Room:
Writing a Book:
This episode offers a masterclass in the art and lifestyle of creating comedy. Tom Segura gives listeners an intimate, practical, and sometimes riotous look behind the curtain—reminding would-be writers and comics that the magic lies in observing, experimenting, and connecting with the audience’s shared experiences and emotions.
For more:
Find “How I Write” and this episode with Tom Segura wherever you get your podcasts.