Tom Segura has been doing stand-up comedy for ~25 years. He's known for his Netflix specials and a TV show called Bad Thoughts.
His stand-up sets are based in stories and simple observations around the world. The guy can look at something you've seen a thousand times but never managed to find the humor in. At one point during the interview I was laughing so hard that I could barely ask the next question.
I asked Tom how he finds jokes, develops stories for the stage, what he's learned from Chris Rock, and how to turn ordinary observations into comedy.
Transcript
0:37 How to find jokes
2:03 Why are comedians always annoyed?
7:19 Say the obvious
11:06 What makes a joke land?
13:11 The 250 rep rule
15:07 Chris Rock
19:33 The 4 types of comedians
21:44 Use the audience’s discomfort
24:39 The key to good stage presence
32:00 Mall cops and TSA agents
36:50 How to develop a joke
38:56 Stand-up vs. TV writing
49:11 Finding your way into the story
54:08 Punchlines
55:16 What a set list looks like
58:15 Word choice
59:31 Accents
1:03:50 How to start a show
1:08:01 Writing a book
David (00:37-00:48)
Do you feel like you turn your comedy radar on and off as you observe the world, or is that just how your brain constantly operates?
Tom (00:48-02:03)
It’s always there; it’s about whether you engage that muscle. You can focus on it and channel energy towards it, or you can choose not to.
It might sound silly, but I believe the best thing a comic can do is simply talk a lot. You’ll naturally say more funny things if you’re talking more. It’s a version of trying things out. You obviously try material on stage, but even off stage, you have certain friends you just bounce ideas off of. The more you do that, the more you develop a skill over time.
You’ll recognize when you’re in conversation and you say something that just has legs—something with potential. That becomes the biggest muscle of all: recognizing, “Oh, that’s something,” versus just casually shooting the shit. Sometimes, something just clicks, and you develop the skill to know, “That’s a thing.”
David (02:03-02:12)
How much of finding jokes comes from being irritated, agitated, or just generally “pissy” about the world? I think of Seinfeld and Larry David; that seems to be a core element for them.
Tom (02:12-02:47)
One hundred percent. Being annoyed is funny. My seven-year-old is annoyed all the time, and he’s hilarious. Sometimes I wonder, “Why are you so annoyed?” Then he’ll say something like, “What’s this table doing in the middle of the room? I keep running into it!”
It’s a funny perspective to be bothered by furniture. He’s naturally funny, but complaining is definitely funny. What’s not funny is total indifference. You realize that when it comes to being funny, you simply have to have an opinion.
David (02:47-02:47)
Yes.
Tom (02:47-05:23)
Exactly. You can say, “This is the best coffee I’ve ever had,” and make that funny, or “This is the worst coffee.” But if you just say, “It’s good,” that’s not funny. “It’s fine. I don’t care,” isn’t funny. It’s funny if you exclaim, “This tastes like someone peed into a cup and boiled it!” Or, “This is God’s gift to the world, I wish I could bathe in this!” You can make that funny. What isn’t funny is lacking an opinion.
Complaining also leads to humor. I love working off of things I’ve overheard—those little moments are some of the funniest things. The small chatter, conversations you overhear, or brief interactions can be gold.
I was just reminding someone of this the other day: sometimes you have jokes that no one ever brings up again, whether you like them or not. Then, there are jokes people remember for years. One of those was when I was checking into a hotel in Charlotte, North Carolina. I gave my last name, and the guy asked, “Am I checking in Segura?”
Then he said, “Oh, Japanese?” I replied, “Yes, one hundred percent.” He continued, “Yeah, we don’t get a lot of Japanese people here.” I looked at him and said, “Well, you do now.” He went on about how they sometimes get French or Spanish guests, but never Japanese. I thought, “Oh, you’re saying it is Japanese. You can say ‘Smith’ and it’s Japanese, but Segura is not Japanese.”
The guy looked at me, dead serious, and said, “You’re not Japanese.” I asked him, “Do you have eyes? There’s a look, right?” He just said, “Oh, I didn’t know.” It was one of those small interactions I brought to the stage, unsure how the audience would respond. They loved it.
The funny thing is, it’s been close to ten years, and people still yell “Segura!” at me on the street. One guy even got a fucking tattoo of my face on his leg in a samurai outfit! I asked him, “What? You want to see me as a Japanese warrior on your thigh?” He replied, “I just love that joke.” I told him, “You have mental problems, dude.”
David (05:23-05:30)
A lot of your jokes are about the awkwardness of conversation.
Tom (05:30-05:31)
Yes.
David (05:31-05:42)
It’s about someone being boring, or just not quite getting it. One of your jokes goes something like: “Where are you from?” “Seattle.” “No way, cool! I have family in Denver.”
Tom (05:42-05:44)
Yes.
David (05:44-05:44)
What?
Tom (05:44-06:24)
Yes, a guy actually said that to me! I also did a joke in a special about walking into a bank in LA. The security guard in the lobby was there, and as a courtesy, I asked, “How are you doing?”
He replied, “Well, I don’t know, man. I haven’t seen my sister in a while, but she’s in Virginia.” I thought, “What the fuck are you doing right now?” He proceeded to tell me his entire life story, all the family drama. I was just trying to walk through the lobby!
David (06:24-06:25)
I just needed a couple of twenties.
Tom (06:25-07:19)
He just kept going on about his family situation, and I had to say, “Okay, thanks.”
It’s those small things that make your antenna go up and you think, “This is funny to me.” Ultimately, in stand-up, whether you’re talking about Seinfeld or any comedian, you’re essentially saying, “This is what I see. This is what I find funny.”
Those little interactions have always been something I’ve reported. Before I was doing stand-up, I would have taken those interactions and told friends and family about them. I would have said, “I was in the hotel, and this guy did this.” I would have told people because I find it very funny.
David (07:19-07:26)
A way to think about it is that there are things we all experience, things we are consciously aware that we all experience.
Tom (07:26-07:27)
Right.
David (07:27-07:31)
For example, we’re conscious that it’s raining outside today.
Tom (07:31-07:31)
Exactly.
David (07:31-07:34)
You know this, I know this. We both had that thought today.
Tom (07:34-07:34)
Yes.
David (07:34-07:40)
Then there are things we all experience that we haven’t consciously thought about, but everyone has, in some way, experienced.
Tom (07:40-07:40)
Right.
David (07:40-07:56)
Here’s another example that has made for so many good jokes over the years: you land the airplane, get to the gate, the pilot dings, everyone stands up, and then you don’t get off the airplane for 15 minutes.
Tom (07:56-07:56)
Yes.
David (07:56-08:03)
It was one of those things I noticed probably 60 or 70 times. Then, suddenly, someone makes a joke about it, nails it, and it’s hilarious.
Tom (08:03-10:19)
It’s hilarious. As a comedian, sometimes it’s one of the most unnerving things, exactly what you’re talking about. You think, “Why didn’t I just say it?” You had the same observation, but you never articulated it. Then another comedian does, and you realize, “Of course!” We’ve all experienced this, but that person was the first one to actually say it.
Sometimes you just have a disconnect where your brain tells you, “You don’t have to say it.” But you get a charge from hearing someone else say it. You realize, “I should be saying more.” It’s like the whole idea of just saying everything.
I was talking to one of my friends because I released a special a few months ago on Netflix called Teacher. Once you release a special, that material is done, so you have to start over again. Normally, I would take a couple of weeks off and then start writing new material.
This time, however, it was the first time in my entire career that the special came out, and then I went right into pre-production for my show, Bad Thoughts. We then went into shooting, and now we’ve been in post-production. It’s been a very demanding schedule, so I’ve never had this amount of time off from stand-up in 25 years.
I told my friend, “I have to get back on stage and try new stuff.” There’s always this familiar feeling where you think, “I have to start over again. How will I ever do it again?” But you remind yourself that it happens every time. I was there again, thinking, “How will I ever do this again?”
My friend, Jeff Tate, a great comic, advised, “Just do them all. Write down all your thoughts, even the dumb ones, and take the dumb ones on stage. Just say them all.” I realized that was the best advice: don’t try to filter through, thinking, “That’s not good enough.”
David (10:19-10:21)
The editor can’t come too early.
Tom (10:21-11:06)
Exactly. Just go say it.
The thing is, when you write down a “dumb” idea and think it’s not worth saying, something magical happens when you get on stage. Between the idea and the performance, you take it somewhere you couldn’t anticipate without an audience. The audience somehow manifests a different thing out of you.
You might think, “I wasn’t even thinking this 30 seconds ago.” But being up there, the mixture of pressure, adrenaline, and thrill all comes together, and something else comes out of your mouth. That’s the part that’s magical and truly indescribable.
David (11:06-11:12)
How much do you think good jokes are about subtext and laying out that subtext?
Tom (11:13-12:07)
It can be that, where you and the audience are heading toward the same destination. I think the simplest way to describe the best feeling of a joke is always the element of surprise.
If the audience is anticipating one thing, and then you turn somewhere else—you say something they weren’t expecting—that’s the biggest rush. Or, I enjoy the idea of upsetting them, having them shake their heads, but still managing to get them to laugh.
That’s also such a rush because they’re laughing against their own judgment. It’s very fun to know they’re thinking, “I don’t like this topic, but damn it, you’re making me laugh at it.” That’s always a fun thing to do.
David (12:07-12:11)
And as a comic, you can point that out, thinking, “Okay, there’s clearly something here.”
Tom (12:11-12:12)
Yes.
David (12:12-12:13)
You’re holding back.
Tom (12:13-13:11)
You actually like this. You think this is funny. Comics usually approach their hour-long sets by building a good rapport with the audience as they perform.
Often, some comics will open with something provocative, but typically, the most shocking material is delivered later in the set. By then, you’ve established goodwill with the audience. In the first five, ten, or fifteen minutes, they’re building trust, getting to know you, and thinking, “I like this guy.”
Then, by minute 25, you can present a truly awful thought, and at that point, they’re on your side. You can get away with more. The comedian does this within a specific bit, but you also end up doing it over the course of your full hour.
David (13:11-13:26)
At what level do you aim to land your jokes? Do you ever feel the pressure to get the words absolutely right? Sometimes I watch comics, and it feels almost like they’re reading a script they wrote long ago; it’s too refined.
Tom (13:26-15:07)
There’s no substitute for performing numerous sets. When preparing for a taping, you want at least a couple hundred runs of that specific set under your belt—literally 200 to 250 performances. This ensures it’s a finished piece of work.
If you’re not taping, part of that journey involves sets that go wrong or moments where you lose your way. I won’t even put tickets for a big show on sale if I haven’t done all that preliminary work. That work is what you remember.
Right now, in this beginning stage, it’s unnerving. You feel totally insecure, but you know that you can achieve it little by little. It’s also the thrill, because you think, “What am I going to do? What am I going to say?”
I’ve started jotting down bullet points: “What about this? What about that?” Next week, I’ll go on stage to do a ten-minute set, and I have no idea how it will go. It could go terribly. I won’t enjoy that, but I understand it’s part of the building process. Being unprepared for a big set is one of the worst feelings.
David (15:07-15:09)
What do you love about Chris Rock’s comedy?
Tom (15:10-15:54)
He is the best at deconstructing an idea. He has a formula: state the premise very clearly, and then break it down. High-level comics dissect concepts from multiple angles, leaving nothing unexamined. They state the issue and then explore it exhaustively.
Rock is incisive, honest, and brutal. People older than me often bring up Richard Pryor, and I understand he was a brilliant comedian. However, the impact of something is also tied to the age at which you experience it.
David (15:54-15:55)
It’s similar to music.
Tom (15:55-16:08)
Yes, like music. It’s even true for sports. People have the “Greatest Of All Time” debate, and everyone 35 and younger says, “Oh, it’s LeBron.” That’s because they grew up
David (16:08-16:11)
watching him. They never saw Jordan in the ‘90s.
Tom (16:11-17:16)
For them, that’s old news. I understand, but that’s what I grew up watching, so the impact is different.
When I was a junior in high school, Bring the Pain came out. It’s a perfect special, so high-level; it just eviscerates every topic. Watching it, I remember thinking, “I didn’t even know someone could perform like that.”
He was such an influence on me. I was so obsessed with his comedy that I have old tapes of myself just starting stand-up, and I’m literally doing a bad Chris Rock impression. At the time, you don’t realize you’re doing it.
Now, when I watch it, I see myself crouching with my hand in a certain way, literally mimicking his cadence and rhythm. That’s what new comics do: you emulate your favorite comedian. He is fantastic.
David (17:16-17:39)
I looked up some good Chris Rock jokes. This one from the 2000s: “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?”
Tom (17:39-17:59)
It’s clever, and it’s very clean. There’s no vagueness to it. Rock’s style really punches you with the message. There’s no nuance to what he’s saying; it’s very direct.
David (17:59-18:04)
Another one: “If you can keep your son off the pipe and your daughter off the pole, you’re ahead of the game.”
Tom (18:05-18:15)
That’s so good. He’s definitely one of the best ever.
David (18:15-18:16)
Have you met him?
Tom (18:16-18:17)
Yes, several times.
David (18:17-18:19)
What have you observed from him?
Tom (18:20-18:54)
The times I’ve met him have all been in social situations, and he’s been super nice, super gracious. I saw him when he came to Austin and was backstage, hanging out.
I’ve always had this approach: if you’re a man ten years older than me, I can’t talk to you like a peer. I don’t know if it’s just how I was raised, but I simply can’t.
David (18:54-18:55)
“Hello, Mr. Rock.”
Tom (18:55-19:33)
Almost. You could tell that a number of these guys just want me to talk to them normally. I don’t think I can.
I’m a super fan in that regard, especially with him and a bunch of guys from that generation. I admire what they’ve done; they’ve inspired me tremendously. I really wanted to pursue comedy because I watched these guys. He is absolutely one of the best ever.
David (19:33-19:42)
How do you categorize the different kinds of comics? For example, there’s the Mitch Hedberg one-liner master, and you’re more of a storyteller. How do you break down these categories?
Tom (19:42-21:43)
Stand-up has never been more popular. The types of comedic communities are much broader than ever before. I remember a time when I felt like I knew the names of every working comedian. Now, it’s out of the stratosphere. I have no idea.
It’s also internationally very popular. There are huge, successful comedians all over Europe, Africa, and South America.
You can break it down. Storytelling is one category. Social commentary is another. There are comics who are really adept at that, like Chris Rock, for part of what he does, and Jon Stewart. Then there are those whose content focuses on hypocrisy, or others who concentrate solely on relationships.
If you want to simplify it, you could say there’s storytelling. Then there’s what I call the traditional American comedian, who’s a mix between a pure joke writer and a storyteller. Finally, there’s the pure joke writer—the person who delivers a clean setup, then a joke, repeatedly. Dave Attell is the quintessential joke writer. Sam Morrell, for instance, just goes joke after joke after joke. Anthony Jeselnik reminds me of that style.
So, you could say there are three main categories. But then, someone might bring up the “alt” type of comic, where you don’t expect any of it, and it doesn’t seem to fit into those established categories.
David (21:44-22:08)
You were talking earlier about having strong opinions. Brian Boltzman, more than any comedian I’ve ever seen, approaches comedy in a unique way. I’ve never met a woman who likes his comedy; whenever I see him at the Mothership with women, they universally cannot stand him. Guys, however, are divided, with about 70% finding him one of the funniest comics.
Tom (22:09-22:09)
Yes.
David (22:09-22:14)
He makes you so uncomfortable. Yet, like heavy death metal, you kind of open up to it.
Tom (22:14-23:39)
He uses people’s feelings about a topic to his advantage. He knows a statement is unsavory, so the statement comes first. You react, “That can’t be your statement,” and then he follows it up with jokes.
This is why I’ve always found it lame when people say, “You can’t say anything anymore.” I tell them, “You can. What are you talking about?” If you feel people are upset when you say something, that’s an advantage. You know they don’t like it, so you can say it, acknowledge their dislike, and then use jokes to support your point.
Even if it’s not truly your opinion, you’re crafting the performance based on knowing that what you’re saying is unlikable. He has mastered that. He knows you won’t like what he says, and he knows how you’ll react. But then he hits you with jokes that follow up, to the point where you either give in or decide to leave the room.
David (23:39-23:50)
Where do you stand on the spectrum of being a comic? Are you someone who’s all about making people laugh, or are you among those who feel a need to say what needs to be said?
Tom (23:50-23:51)
I’m definitely not the latter.
David (23:51-23:52)
Not that.
Tom (23:53-24:39)
No, I’m not that smart, and I don’t feel a strong urge to get a message out into the world. I enjoy performing, doing stand-up, and making people laugh. I also like to laugh myself.
For me, it’s just fun. There’s no thrill quite like getting on stage with an idea and making people laugh. That’s the drug, the addiction. It’s why you see comics perform into their nineties—it’s a thrill, and you just want to keep doing it. I don’t have that “the world needs to hear this” mentality. I’m not that guy.
David (24:39-24:42)
Who do you think has incredible stage presence? I saw Joey Diaz.
Tom (24:42-24:44)
Oh, my God.
David (24:44-24:44)
He just gets up there.
Tom (24:44-24:45)
He’s a tornado.
David (24:45-24:46)
A tornado.
Tom (24:46-24:47)
He is a tornado.
David (24:47-24:49)
Unbelievable. Who else have you looked at?
Tom (24:49-25:15)
The perfect stand-up, if you want to call it that, is someone who combines incredible stage presence with strong writing. That’s what makes a great stand-up comedian.
Sometimes you watch someone and think, “This person is a great writer, but their presence isn’t as strong.” Other times, people are more presence-heavy, and their writing is just okay. The ideal is a combination of both.
David (25:17-25:17)
Right.
Tom (25:17-28:57)
He takes over a stage, and it’s just undeniable. Sometimes, the presence itself is what truly excites you, or what you realize you’re responding to is how comfortable the performer is. Their presence can be a powerful force that makes you think, “Oh, my God.”
A number of people come out with that kind of energy. They come out hot. Leslie Jones, for instance, projects an energy that immediately commands your attention. Dave Chappelle, while obviously very famous, exhibited this putting-you-at-ease quality even before he became a superstar. You don’t feel jumpy; you simply think, “This person knows what they’re doing.”
This is a huge advantage for a comedian: putting people at ease with your charisma or comfort on stage.
I remember seeing Jerrod Carmichael years ago. He was about 21 at the time. When he walked on stage, I couldn’t tell his age. Afterward, I asked him how old he was, and he said 21. I was stunned.
The way he carried himself during his set made me think he had been performing for at least 15 years, when in reality it had only been about four. That level of comfort is incredible.
Ultimately, the goal is to be a presence on stage that makes people feel at ease, unless your act is designed to be a tornado of energy. For me, I want people to feel confident that I know what I’m doing.
One thing you notice about stage presence and performance over time is that good, seasoned performers are not afraid of silence. They use it to their advantage. New comedians, however, are terrified of it. They become literally jittery if a few seconds pass without laughter.
You’ll see them deal with this in different ways: getting loud, becoming frantic, screaming—anything to push past the uncomfortable silence. Super seasoned comedians, though, understand that if they aren’t frantic and their words are leading somewhere, the audience will slowly lean in.
Suddenly, you realize everyone is intently watching the performer. The audience isn’t thinking, “Where are the laughs?” They’re thinking, “I’m following what you’re doing.”
Dave Chappelle is an extreme example. He’s not just a comedian; he’s an orator and a master at speaking to people, and he uses that skill set in his comedy. I’ve been in arenas with him where 18,000 people are present, and you can hear a shoe move. It’s incredible to witness.
David (28:57-29:17)
Craig Ferguson, the retired late-night host, would get on stage and say, “Want to have an awkward silence?” He’d then be completely silent and say, “Oh, it’s fine.” My sense is he probably did 20, 30, or 40 of those, became comfortable with it, leaned into the bit, and it always ended up being funny.
Tom (29:17-29:18)
He’s so good.
David (29:18-29:18)
He’s so good.
Tom (29:18-30:00)
He’s excellent at navigating moments when things aren’t working and making them work. It truly feels like he’s just not scared.
What I’ve learned about getting on stage is that you feel different emotions every night. You’re not the same person walking out there each time. Sometimes you’re confident, sometimes overly confident, scared, nervous, or angry. You feel all these things. I’ve found that the best mindset for me to go on stage with is silliness.
David (30:00-30:01)
Yes.
Tom (30:01-30:35)
When you’re backstage, literally goofing off with your friends, telling silly jokes, genuinely laughing and having fun, and you take that energy on stage—for what I do, that’s the best way to perform. You can try to manufacture it, saying, “Let’s be silly, let’s not be serious,” but when that genuine silliness is truly happening, those are always the best sets.
David (30:35-30:55)
Do you find that people can help you get into that mindset? For me, I can’t just be told, “Okay, David, be silly.” I can’t force it. But if my sister walked into the room right now, you would see a level of silliness emerge from me that I simply cannot create on my own, and it would happen instantly.
Tom (30:55-31:54)
If you were a touring comedian, I would tell you to bring your sister on tour. Seriously.
You end up constructing this whole team. When I go on tour, I have a tour manager, tour coordinator, production manager, security, a merchandise person, a photographer, and opening acts. All these people travel with you from city to city. It’s crucial to be silly with them. You want to feel comfortable with your crew.
When we’re in a good place, we’re laughing and joking around, maybe about someone working there, like, “Look at this lunatic!” We’re having those conversations backstage, and then they announce you. You take that energy onto the stage. It’s a much better energy to hit the stage with than being down or super serious.
David (31:54-31:55)
You don’t want to think, “I need to nail it tonight.”
Tom (31:55-32:00)
Exactly. You don’t want to hit the stage thinking like that. I certainly don’t anymore.
David (32:00-32:17)
You don’t really strike me as a “one weird trick” kind of guy. Are there things you consistently find funny? For example, mall cops have about five out of ten authority, but they treat it like they have ten out of ten.
David (32:17-32:20)
It’s as if they work for the IDF or something. It’s always funny.
Tom (32:22-33:36)
It is always funny. You’re right about people who want to exercise the little bit of power they have. You see it and immediately understand what’s happening. Even with TSA, you realize that some agents, who are telling you to “give me your ID” or “stand here,” are really flexing their authority. You wonder, “Are you a corrections officer? Who do you think you’re talking to?”
I had one experience where an agent tried to embarrass me in the security line. She said, “You got in the wrong f***ing line.” I just stood there. Then she asked, “Do you not read your pass?” I thought, “What do you think you’re doing right now?” A guy nearby, someone I didn’t know, tried to interject, saying, “Hey, chill, you don’t want to get in trouble.” I wasn’t worried about that person. She’s a TSA agent, a glorified mall cop. If you’re going to flex on me like you’re a special agent, I’m going to call your supervisor.
Tom (33:36-33:38)
I told them, “You’ve got to retrain this woman.”
David (33:38-33:40)
It’s the same thing with bouncers at a middling bar.
Tom (33:40-34:14)
It’s exactly the same thing. Someone with no power in the world is given three square meters of dominion and told, “You are the most powerful person here.” Then their true nature comes out. That’s exactly what it is.
It’s like crossing the street slowly when cars are coming, trying to show everyone you have control. But you can get hit by a car, too.
Tom (34:14-34:32)
The TSA agents, of all people, are fascinating. I’m sure it’s not the most thrilling job, but when they flex on you, it definitely spins me out. It’s pure mall cop energy.
David (34:32-34:33)
It is mall cop energy.
Tom (34:33-35:32)
The longer you do this, you start thinking, “Oh, I have a take on AI,” for example. Then you go to the club that night, see fifteen people doing AI bits, and think, “Okay, I’ll do mine if I feel it’s far superior to these others.” Otherwise, you don’t.
This led me to do so much storytelling about my own life: stories about my kids, my mom, my friends. You tell these stories because you realize no one else has that exact story or perspective. It stems from my love for storytelling, coupled with the knowledge that this specific experience is unique to me.
David (35:33-35:38)
It’s like the In-N-Out Burger bit where they humiliate you for eating in the car.
Tom (35:38-36:14)
They’re basically asking, “Are you fat? Do you want to eat in your car like a fat boy?” And then they hand you an open pig trough. You think, “Okay, I guess I’ll eat out of that.”
I almost feel like when they first ask if you’ll be eating in the car, you want to say, “Hell no, I’m not a f***ing loser.” But then you actually think, “Yeah, I kind of do want to eat in the car.” When you have observations like that, specifically the In-N-Out one, you realize you have to get it out there. Someone else is going to say this; it’s inevitable, so I have to do it.
Tom (36:15-36:50)
You know other people are clearly experiencing this, too. I remember sometimes on tour, even with that bit, I’d be doing it and it would be clicking with audiences. You think, “Man, I’ve got to get this special out.”
You feel this relief when you get it out there, because some observations feel so universal that someone else has to be making them. There’s an urgency to get it out.
David (36:50-37:04)
You’ve got me thinking about the connection between shared frustration and the core of a joke. What is the joke here?
The thing that has frustrated me to no end is how every concert opener just sucks.
Tom (37:05-37:06)
Do they all suck?
David (37:07-37:12)
In my experience, perhaps that’s too harsh to say, but concert openers are just terrible.
Tom (37:12-38:12)
As we were saying, complaining is part of what’s funny. Your observation is valid. Keep talking about how bad it usually is; that’s where the joke lies. Sometimes the too-obvious thing isn’t the joke because it’s simply too obvious.
The joke lies in digging into the feeling of what’s bothering you. As long as you keep expanding on why it upsets you, the joke will reveal itself. What upsets you? Is it wasting time, or that you showed up early? The joke is in there. You just have to keep digging in.
Didn’t you ever think, “Just show up later”?
David (38:12-38:16)
But if you miss the main thing, the whole night is ruined.
Tom (38:16-38:22)
But if the show starts at eight and you know the main act isn’t going on until nine?
David (38:22-38:25)
No, if it’s till eleven, I’m not showing up till 10:30.
Tom (38:25-38:28)
And even that 30 minutes bothers me. Bullshit.
David (38:28-38:30)
Of course it bothers me.
Tom (38:30-38:55)
The joke is that you’re bothered by hardly any time. That’s what’s funny. You’re not spending three hours watching some bullshit; you’re spending 15 minutes and you’re annoyed. That’s what’s funny to me.
What are you talking about? You can’t sit through 15 minutes of something? It’s like somebody yelling at the trailer before the movie. You’re like, “Bro, just eat some popcorn. What is your problem?”
David (38:57-39:13)
How do you feel you’re able to tell a joke in the Bad Thoughts TV show versus stand-up? What do the different mediums afford you?
Tom (39:13-41:46)
It’s so dramatically different and so fun. In stand-up, it’s “here’s a thought,” “here’s an observation,” or “here’s something that happened,” and you paint your picture with words. You tell it. As I said, 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 a few drafts and we’ll read it in the room. You’re there with other comedy writers, which is exciting because this is something you don’t do in stand-up. You don’t go, “Here’s my stuff,” and then sit with six comedians asking, “What does everybody think?”
Sometimes they’ll tell you, “I think this,” or they’ll give you a tag you should say at the end. You think, “Oh, that’s a good idea.” But it’s not a fully collaborative process.
A writers’ room, however, is so much fun because you’re sitting with these other comedy minds, hearing things from all different angles. It becomes an “Oh, my God, I didn’t think of it like that” moment. Sometimes I’ll want to tell a story a certain way, and one of these people will either find a hole in the story or bring up something else that sparks a new direction for my mind.
That’s the biggest thing about a writers’ room that people might not realize. Yes, sometimes I can say, “Here’s an idea,” and somebody goes, “I have a take on it,” and they’ll take it somewhere else. But other times, I say something, another writer says something, and it sparks my own idea, which feels so exciting. You realize that without them having said something, your mind would not have gone to this other place. That’s a really exciting dynamic.
Specifically with Bad Thoughts, we get to do mini-movies, like little crazy short films. The fact that you get to come up with this concept, paint a real picture, have it shot cinematically — we have a very cinematic look — and then bring in other actors that just elevate the whole thing, it is one of the most fun experiences I’ve ever had.
David (41:46-41:54)
What kind of TV did you look at the same way you looked at Chris Rock? Where you thought, “I like that, I want to incorporate this, they’re really inspiring me.”
Tom (41:55-43:24)
From the early onset, I grew up in the era of many sitcoms, so I watched Seinfeld, Cheers, and Roseanne. Then I got into more dramas as they improved, shows like The Sopranos and Breaking Bad, which were so great.
When we were pitching Bad Thoughts, I actually funded and made the pilot so I didn’t have to just pitch an idea; I could say, “Here it is.” One of the lines we used was, “This is like Black Mirror, but a messed-up comedy version.”
What I loved about Black Mirror is how they take these ideas, twist and turn them, but also immerse you in this world and make it very cinematic. To me, the visual look is a huge factor in the show. You really want that.
The fun thing about Bad Thoughts is that Netflix also just says, “Make what you want to make. Do your thing.” They give us suggestions, like, “What if you did this?” or “What if you leaned more on this?” but they don’t say, “You can’t do that.”
David (43:24-43:37)
As I was asking that question about what you can achieve in stand-up versus a sitcom, I think the ability to act something out, to take something small and make it a little bit more ridiculous...
Tom (43:37-43:37)
Yes.
Tom (43:38-45:51)
My favorite from this season is one of my favorites, I should say. It came from an idea I had while sitting in the van after a show. We were being driven from the venue to the hotel, and Kirk Fox, a comedian and actor, was with me.
We started discussing, “Wouldn’t it be really funny if a comedian’s merchandise was something unconventional and ridiculous to sell, something inconvenient for both the seller and the buyer?” We laughed so hard in the van, tears streaming down, doubled over, just kept riffing on it. I laughed so much that I decided to write it. I thought, “I’m going to take our make-believe hypothetical thing and write a draft of it.”
So I wrote a draft and brought it to the writers’ room. People reacted, “This is insane.” I clarified, “Is it good insane or bad?” They said, “No, it’s funny, but we play it like this is the most sincere thing.” That’s the most fun thing to do: take an absurd idea and play it seriously.
There are moments like that in the writers’ room where you question if you’re actually going to do an idea or not, because you always have more ideas than you can shoot. I kept putting this one on the “we’re doing this” side of the board. Sometimes people would move it, and we’d bring it back. Eventually, we ended up doing it.
It still makes me laugh almost as much as it did that first day. It’s so fun to take something hypothetical and actually put it on screen as a real thing. To me, that’s the equivalent in stand-up of having an idea and taking it on stage. You think, “Oh my God, what a thrill that I got to say it on stage.” In Bad Thoughts, you can have these silly ideas and actually shoot the scene with the dialogue and setting, making it a tangible thing. That one truly makes me laugh so hard.
David (45:51-45:53)
I love when a bit...
Tom (45:53-45:53)
Yes.
David (45:53-46:00)
...gets in your head, and then you start seeing it all over the place. That bit lives with you. That’s what’s so fun about a skit.
Tom (46:00-46:01)
Yes.
David (46:01-46:03)
Or a sketch. You can just bring it to life.
Tom (46:03-46:04)
Yes.
David (46:04-46:17)
It’s the perfect amount of exaggeration. How do you exaggerate enough to make it funny and absurd while also retaining the reality of the situation? It feels like something that could happen in your life and probably has.
Tom (46:17-47:20)
For me, the formula for taking those ideas and putting them on screen is to emphasize that it’s grounded and real. In casting, for instance, we’d look at potential actors. You have great comedy actors and then you have dramatic actors. We would go for the dramatic person. Get the dramatic person to deliver this material because it gives it weight, grounds it, and makes it real.
The more ridiculous an idea is, the less I’d want a comedy actor; I’d want a drama actor. That’s the most fun: taking the craziest idea and making it seem like you’re doing Shakespeare or something. That’s the most enjoyable part.
David (47:20-47:24)
It’s funnier if they’re not trying to be funny.
Tom (47:25-49:10)
That’s the key to it all. It’s funny if both characters are playing it super real. The longer you hold onto that real amount of time, the funnier it becomes.
It’s similar to how comedians get nervous with silence. In television and film today, you’ll notice fast edits happen so much. If you watch European films versus most American studio films, American studio films have an edit every three seconds. Sometimes you’ll watch a European film where a guy making coffee is captured in a single shot. It shows him putting water into the thing, you watch the whole thing fill up, and then he presses the button.
You watch it, and then you realize, “Oh, I’m not anxious watching this. I’m watching somebody make coffee.” That’s how it is; it’s real. The comedy of that moment relies on you actually having the time where the guy is waiting. The waiting makes it feel real, and then you think, “God, that’s so long.” You have to hold that. You want to sit in the real tension of a 25-second door hold, which is so long to watch. That’s why it’s funny; if she doesn’t try to make it funny, or if he doesn’t do this, it becomes funnier because it’s real. The realness of it is what’s funny.
David (49:11-49:17)
When you’re telling stories on stage, what have you learned about setting the premise?
Tom (49:18-52:14)
One of the big things people always talk about when doing standup is having a story but wondering about the “way in.” The reason for telling a story is often as important, if not more so, than the story itself. It gives it weight; people think, “Oh, this is a funny story, but the reason for telling it is just as important.”
That’s where much of the work in standup comes in. It becomes a puzzle: Why am I telling this story? Am I just stating that something happened, and maybe it’s funny?
For instance, I told a story on my last special about when I almost booked the campaign to be the spokesman for Subway years ago. I booked it, and I was going to do it with Jared from Subway. I tell the whole story.
You could just say, “One time, I was almost the spokesman for Subway. Here’s what happened.” You could tell it that way. But on stage, I started by saying, “I’m so grateful to be performing here, doing this show. I never thought this was in the cards for me, being able to do arenas, amphitheaters, and huge theaters. I thought the highlight of my career was when I booked the campaign to be the spokesman for Subway.”
Right there, you give yourself a reason to tell the story. It’s different from just saying, “I was almost a spokesman for Subway one time,” because then people might just think, “Oh, that’s cool.” But if you connect it to, “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 booked this,” then you have a reason. They’re engaged before you even start.
I feel that’s a lot of the work, especially for storytelling. You have a story, but you need to figure out your way in. Figure out a reason for saying it, even if it’s something like that. You want to dig and not get lazy about those moments; you want to figure out why.
David (52:14-52:59)
I talk to a lot of storytellers about how I write, and they’ll say something similar: you want to set the stakes to show people why what you’re doing is important. A lot of the art in more baseline stories lies in making those stakes clear.
For example, if I were to say to you, “My apartment was a mess. It smelled like weed,” you might think, “Okay, that’s fine. That happens to a bunch of single guys.”
Now, imagine if I said: “I just moved to New York. My parents were a little worried about me, and we fought a lot about the move. This was their first time visiting, and I wanted to show them I’m a real adult now, that this was the right decision.”
Tom (52:59-53:00)
Yes.
David (53:00-53:08)
“Now they’re visiting. They just texted me, ‘Hey, we’re here to surprise you. We’ve just landed at Newark. We’ll be there in two hours.’”
My place is a mess.
Tom (53:08-53:09)
Smells like...
David (53:09-53:10)
...weed.
Tom (53:10-53:10)
Right.
David (53:11-53:12)
That’s a whole different scenario.
Tom (53:12-54:07)
That’s exactly right. You’ve created stakes and pressure. Now the audience knows you could really disappoint your parents. The stage version of that is figuring out your “way in.”
You could simply say, “My place is dirty, smells like weed. My parents aren’t going to like it.” People would understand that. But if you tell them the backstory first and then get to that point, it becomes much more impactful. You have a clear reason for the story.
I try to spend time figuring out that reason. You know when you get it wrong because you just told the story without that setup. It might get laughs, but you realize that if you had done the work to set it up properly, people would be far more invested in the story.
David (54:08-54:12)
When I think of jokes, I think of punchlines. Do you think of punchlines a lot?
Tom (54:12-55:16)
The way I approach storytelling is, the first time I tell it, I go with the super long version. I don’t go into it thinking it has to be a certain way.
You realize the story is “fat”—let’s say it’s seven or ten minutes long. Then you begin the editing process. You identify what information isn’t needed, making it tighter.
After that, you go in and think, “I need something here, something here, something here,” which means adding jokes and punchlines throughout. Ultimately, you love to end one of those stories on a big punchline. That’s more rewarding when you finally solve it, because sometimes you know there’s something there, and then one day, you find it.
However, there’s also something soothing and pleasing about the times you just go on stage the next day, say the stuff, and it all works. It all comes together with tension, rhythm, and punchlines.
David (55:16-55:17)
So, what does a set list look like?
Tom (55:18-55:21)
It’s usually just one word for each topic.
David (55:22-55:25)
Augusta. Mansell. Blackout drunk. Hitler.
Tom (55:25-58:15)
I was fascinated by the Hitler thing. I watched a documentary that detailed his drug use. Everyone with World War II knowledge knows the Germans used methamphetamines, but the documentary revealed he was also doing cocaine, given to him in the mornings by his personal doctor.
I just went on about how that made more sense. He’d wake up, and his doctor would give it to him. He’d do a rail and say, “Juice!” If you have a heart full of hatred and cocaine, it’s not a good formula. We talked about how his “coked-out” behavior made sense. He’d be like, “You guys, my new I shaves the sides off,” showing his mustache, “You guys want to see my art?” Just ranting and raving.
That’s one of those jokes where you watch something, talk about it on stage, and then realize it’s a bit. The idea of turning it on or off is that you just talk about things that enter your mind.
I also talk about my kids. I’ll talk about what literally happened with them. Audiences will tell you what’s a bit and what isn’t. Sometimes people say, “Oh, I know you made that up about your kids.” I tell them I don’t make up a single thing about those guys. There’s nothing invented. If you have kids, you’d understand this is really what happens.
My kid once yanked a duck out of a pond by its neck and asked, “Can we take this home?” I was like, “Are you out of your mind?” I just told the whole story, and people with kids, especially boys, go, “Yeah, I get it.”
David (58:15-58:22)
How much do you think about word choice? “Yanked” is a way funnier way to say that than “my kid pulled” a thousand percent.
Tom (58:22-58:36)
Sometimes you’re heavily conscious of it when you’re in the mindset of what’s funnier because there are words and sounds that are funnier.
David (58:36-58:37)
Yeah.
Tom (58:37-58:37)
Funnier.
David (58:37-58:41)
It’s just Yiddish things are just universally hilarious.
Tom (58:41-59:31)
It’s like when somebody says someone got “clipped” by a car instead of “hit.” “Clipped” is a funnier word than “hit.” There are all these little things you start thinking about. When you’re really dialed into the funniest version, that’s part of the work.
Sometimes you’re also sitting around talking with people, especially in offstage conversations, and funny people describe things in a funny way. You realize, “Oh, that’s how to say that.” Like, the guy didn’t get a hand job; he got “tugged.” That’s funnier. Your ears just pick up on these things, and you’re like, “That’s definitely funnier to say.”
David (59:31-59:40)
How did you realize that accents and sort of merging into other languages real quick was so funny? Because you do that with Spanish.
Tom (59:40-1:00:40)
Oh, all the time. From when you’re a kid, you realize that an accent is hilarious. I’ve always loved languages, learning about them. I use three Duolingo-type apps all the time. I’ve always liked languages, and there’s something about people pronouncing things that’s just funny.
It also paints a picture. If you say, “I was in the store, and the first one was like, ‘Are you looking for something?’” versus “Are you looking for something?” you imagine a different person. It adds color to the story. So, doing accents and voices is a huge part of making it funny.
David (1:00:40-1:00:40)
It’s.
Tom (1:00:40-1:01:04)
Yes, I talk about my mother all the time; her accent is strong. She’s from Peru. She’s still Howard Jew, and I’m like, “Jesus, I’m Catholic.” She has a very strong accent. There’s that hilarious Hilaria Baldwin thing that went viral.
David (1:01:04-1:01:05)
No, what was this?
Tom (1:01:05-1:01:11)
She’s American, but I guess she spent a lot of time in Spain growing up.
David (1:01:11-1:01:11)
Okay.
Tom (1:01:12-1:03:44)
She’s American, from Boston or something. She was doing an interview for a recipe, and they asked her how to make something. This is Alec Baldwin’s wife, I think, right? She said, “You slice the tomatoes, and then you slice up... how do you say in English? Cucumber?” I thought, “How do you say it in English? That’s your first language! What are you talking about? You know how to say it in English.” She didn’t say, “How do you say that?” She said, “How you say in English?” as if she had been teleported to a Spanish-only speaking world. It was insane, and I roasted her so hard.
Then something happened to me that showed me there’s always karma. I forgot that if you are bilingual or trilingual and you start speaking one of those languages a lot, especially a second language like Spanish, and you’re immersed for a period of time, you literally do run into moments where you think, “Wait, what’s the word again?” for your native language.
It happened to me after I roasted her so hard. I went on a South America tour, so I was in Argentina, Chile, Peru, and Mexico City. At one of those airports, somebody came up to me and asked me to sign something. I had been speaking only Spanish 24 hours a day for a couple of weeks.
They gave me the pen, and I asked, “What’s the name?” They replied, “Oh, it’s for my son, August.” I wrote “August,” then I put a comma, and I thought, “How do you say in English, ‘I wish you well’?” I couldn’t think of the words because my brain was stuck.
I realized, “Oh, I’m a hypocrite.” This really does happen. If you’re immersed enough, you’ll forget basic words. It was one of those things where I had to go on a podcast and say, “Sorry, Hilaria. It happened to me too.”
David (1:03:45-1:03:46)
Sorry.
Tom (1:03:47-1:03:49)
I guess it is a real thing.
David (1:03:50-1:03:56)
What have you learned about opening bits? When you walk out, what’s the first thing you say?
Tom (1:03:56-1:05:04)
I have done every version of how you can open a show. I’ve done the slow burn, where you walk out and say, “How’s it going?” taking your time to ease into the show. I’ve also done the hardest joke I can think of right out of the gate, and everything in between.
There are valid points and advantages to each approach. Ultimately, I think opening with a strong joke is the best way to go, having tried them all. You could ask me on a different night, and I might prefer another method. It’s all about experimentation, having fun, and trying new things. But if I had to recommend one way, I’d say open with a strong joke.
David (1:05:04-1:05:15)
I’m amazed watching your sets, thinking about even dinner conversations, how funny callbacks are. You’re sharing information, but you’re also creating a world.
David (1:05:15-1:05:20)
There’s something about calling back to something in the world you’ve established.
Tom (1:05:20-1:05:30)
Callbacks are fantastic. What you become aware of, and want to avoid, is overdoing it.
Tom (1:05:31-1:06:21)
You don’t want to overdo anything. Some comedians use callbacks constantly. When you cleverly place them, however, and find the perfect amount, it works really well.
You also see how much a live audience loves it. It’s similar to a conversation where a callback shows the other person you’re paying attention. It comes across as charming and smart; you think, “Oh, this person is witty. They remembered what we said five minutes ago.”
When you apply that to an hour-long presentation, having a few carefully placed callbacks is fun. It shows you’re thoughtful, and audiences, when they’re dialed in, absolutely love it.
David (1:06:21-1:06:39)
That gets to a deeper point about comedy: the line between extremely funny and extremely annoying is actually pretty thin. We all had that friend growing up who would make a joke and then say, “Oh my God, that’s funny!” They would never stop making the joke.
Tom (1:06:39-1:06:40)
Try having kids.
Tom (1:06:42-1:07:59)
Kids don’t realize that. The first time they make you really laugh, you can see it in their eyes. They’re like, “What’s going on?” You ask, “What did you say?” They repeat it, and you keep laughing. It’s exciting for them. They think, “Oh, I can have this effect on someone.”
It’s a new sensation for them, to say something and have someone double over laughing. Then they inevitably say it 3,500 times. You have to tell them, “Hey, that’s not funny anymore.” They ask, “Why?” and you say, “Because you said it too much.”
That can happen with adults and comedians, too. Repeating the same point over and over loses its impact. That’s why I think the key element to what is funny is surprise. You want to be surprised. You laugh the hardest when you didn’t expect it, when it catches you off guard. Whether it’s a kid at home or someone sending a message, you want something unexpected to be said.
David (1:08:00-1:08:06)
As you were writing your book, what was different about that kind of comedy versus the show and stand-up?
Tom (1:08:07-1:10:30)
The book was one of the most rewarding and challenging experiences for me. It’s not a particularly deep book, but I wrote many stories from my life.
I found that having a great editor and publisher was crucial. Stand-up is a solitary endeavor, and television or movies are huge collaborative efforts. Book writing, however, is a dance, like a marriage between just the two of you.
I had no idea what I was doing, so I would write pages and send them in. The feedback was never consistent. One chapter might come back with a note saying, “This is perfect. This is what the book should be.” You’d feel great, thinking you’d mastered it.
Then, the next chapter would be heavily edited, with comments like, “What is this? Needs humor here. This doesn’t connect.” It was jarring.
It felt like a math problem or a puzzle I had to solve. But I wanted to solve it. I’d think, “No, I like this story, I like this world,” but she was brilliant, and I knew she was right. I had to readdress it.
I enjoyed the challenge. It was a tremendous amount of work, even though it wasn’t a 400-page book. It truly takes a lot; you have to love the process to see it through.
As soon as it came out and performed fairly well, they asked if I wanted to write another book. My immediate thought was no; it was so much work. It’s not that I would never do it again—I would—but at the time, I needed a break.
I couldn’t believe how much goes into it. It made me appreciate authors who do this for a living so much more. Having had the experience, I can say it was a lot.
David (1:10:30-1:10:39)
One thing you said about it was that you didn’t have other things to lean on. No pacing, rhythm, or diction. All you had were words.
Tom (1:10:39-1:11:48)
It was the most exposed and vulnerable I’ve ever felt in any art form. As a stand-up comedian, I control so much with my delivery, cadence, facial expressions, and the way I say things.
You have all this power, but when you hand over pages of something you’ve written, you experience crippling anxiety. You wonder if any of it will translate as you intended. I’m not controlling the cadence anymore; it’s the written word.
A part of you feels like someone will say, “What is this?” That’s how it feels when you hand it over. You’re just waiting for them to say, “Yes, this is fun!” You’re surprised when they do.
David (1:11:48-1:11:51)
You’re used to instant feedback, a thousand percent.
Tom (1:11:51-1:12:35)
The waiting was agonizing. “We’ll get back to you in a week.” A whole week! Can you imagine performing stand-up and asking the audience, “Let me know how this goes next week”? You expect an immediate response.
That was some of the most anxious I’ve ever been. It was that uncertainty: “Are you reading the words the way I intended them?” In stand-up, I know how I’m saying it, and I know how it’s landing.
The difference between the two art forms was massive. It was terrifying, truly terrifying. Ultimately, it was a super rewarding experience, and I’m really glad I did it.
David (1:12:36-1:12:37)
It’s great to meet you, man.
Tom (1:12:37-1:12:37)
You too.
David (1:12:37-1:12:38)
That’s fun.
Tom (1:12:38-1:12:39)
Thanks so much.
