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Behind every great roast joke is a writer who just wants to make you laugh. While the millions who tuned in to the The Roast of Kevin Hart saw a star-studded dais skewer the uber-famous comedian, Madison Sinclair was one of the behind-the-scenes writers supplying the faces of the event—such as basketballer Draymond Green, Grammy winner Lizzo and Dwayne “The Rock” Johnson—with their hilarious, and often cutting, words.
You might know Sinclair from her viral fame: Across TikTok and Instagram, videos featuring her tormenting her dog with “Walks Into a Bar”-style jokes have wracked up hundreds of thousands of views. But she’s also been a huge part of the “event television” roast ecosystem for some time, having worked on The Roast of Alec Baldwin, as well as The Roast of Whitney Cummings for OFTV, the network owned by OnlyFans.
Her favorite kind of roast joke, she says, is a puzzle—one that has multiple layers and can act as both a compliment and an insult. And while roast jokes are meant to go a little too far, even veering over the line of political correctness, that’s the point. In fact, she said, it’s a little bit “impressive” when a joke can still make her squirm a bit.
“I never want to be at a roast where I’m comfortable with every joke I hear,” she told Playboy. “That’s kind of the fun of them.”
In an interview with Playboy, Sinclair spoke about why jokes that go hard have to be smart, why Dwayne Johnson wanted Kevin Hart to suck on his nipple and what Caitlyn Jenner said when confronted with a joke about her vagina.
You’ve written for a lot of roasts. How did you get the gig to write for The Roast of Kevin Hart?
It started with doing a roast battle when I first moved to LA. I used to have really bad stage fright and roast battles terrified me more than anything because you didn’t know what kind of insult someone was going to come at you with. It’s a mix of joke writing and improvising, and I’ve always really favored joke writing. From there, I just fell in love with it because it’s one of the two forms of straight joke writing. When you watch, it’s just nothing but one-liners.
What goes into a good roast joke?
My favorite roast joke is if it’s a puzzle, and if you can compliment someone while insulting them. Like if you’re going to do a fat joke about Lizzo, I like the one where they said, “Kevin has two Grammys, Lizzo has 8 — everything ever put in front of her.” It highlights her accomplishments and includes really high praise, a compliment and an insult together.
Or if you can get two people at once, like when someone said, “Chelsea Handler looks like she could be Shane’s mom,” and you just assume it’s going to be an old joke and it’s “because he looks like he has fetal alcohol syndrome.” You can call someone old, an alcoholic and you can say someone looks like they have a disease all in one sentence.
What do you think makes roast so popular? I feel like they’re, they’re even more popular now than they were a few years ago.
People like jokes, and it’s fast paced. Some people are up there for only three minutes. It helps with people’s short attention spans. The Netflix ones in particular, even though the live element is a producing and logistical nightmare, there’s such a risk of things going horribly wrong that people like to watch. There’s no event television anymore. Having any kind of event television is really fun. I know very little about sports, but I enjoyed the Tom Brady roast just because it was live. People are drinking, too. It’s risky. I think you will tune in to see what can go wrong as much as they go to see the jokes.
You had shared with Variety some of the jokes that you had written that were cut. At what point in the process do you learn something has been cut? Is it very early or day of?
It’s a mix of both. Some people are really close with certain celebrities. The best example would be Lizzo, her boyfriend’s a comedian. So that’s the comedian that’s going to be working really closely with the talent. Dave Sirius works really closely with Pete Davidson. Mike Lawrence works very close with Pete Davidson; they’re very close friends. It’s assumed the script is going to be a collaboration between them and their very close-knit writing team.
I’m someone who’s more of a joke machine. There was no one on the dais that I’m particularly close with. I’ve worked with Jeff [Ross], on like 12 projects or something. I’ve known him since I was 21. So I was just writing general jokes and the head writer marks them as “A jokes” or “B jokes,” and then divides them and then offers them to certain people. Some people need more jokes than others. Like I would say that Draymond is a good example, an athlete who’s never done comedy before versus someone like Chelsea Handler who, even though she’s not a big roast person, she’s been a comedian for so long. She’s a veteran comic and she has her own writers that she works with. She doesn’t really need a bunch of jokes from someone she doesn’t know.
In roasts, people go hard, and it can be really going for the jugular or “un-politically correct.” What do you say to people who might think roast jokes go too far?
I will say, sometimes people are right. Personally, I don’t love colorism jokes. They just don’t make me laugh. But if you’re able to tell a joke and people laugh, it’s undeniable. And you really do have to go for it. Most of the people I disagree with. I think that it’s fun to have a joke that is so awful. I think it’s kind of impressive when something can make you that uncomfortable. But at the same time, there’s definitely a lazy route.
I don’t think they’re trying to censor people, but they are just asking for a more interesting angle. They’re not saying that you can’t go for racism or homophobia, but if you’re going to do it, you better do it correctly. If you’re going to make fun of a sensitive topic, you better have a really smart joke about it. And the punchline isn’t just that — you’re saying a slur!
You also wrote for OnlyFans roasts.
It was a really cool experience because OnlyFans TV was trying to make content that was just kind of like their own TV channel and trying to have event television. They were censored like crazy. It’s really ridiculous. The way that social media comes after and censors people who are doing any form of sex work, I think is insane. And even when we were just doing comedy, everyone’s clothed, they still had to fight with censors with how we were promoting it.
But OnlyFans is great, they gave the keys to Whitney for two roasts and she just ran the room in such a fun way and she’s a really talented joke writer. Every day we’d just go in and we had a room that was a little bit chaotic where we would be writing all these jokes.
One day, she’s like, “Hey, Rick Rubin’s going to come in.” And I was like, “To pitch?” And she’s like, “No, he just wants to experience a joke writing room.” He comes in without any shoes looking like a vagrant, sits on her dog bed, closes his eyes in a meditative state and listens to us pitch and he ends up falling asleep. Then he said “Thank you,” and he left. And we all just kept writing jokes.
Did anyone this time around present any particular problem to you as to figure out how to make it funny or how to make fun of them?
People came in with insane ideas this year. Lizzo pitched her having the flute and pied pipering out a bunch of little people that are dressed as Kevin Hart. And we were just like, “Oh!” Because if anyone pitched that, they would be like, “We’re not going to call Lizzo and, with all she’s accomplished, ask her to do that.” We would never pitch that.
It’s really fun when people come and pitch things to you because you’re able to do things that usually the executives would never even try to touch. Dwayne Johnson wanted to try to get Kevin Hart to suck on his nipple. We could never pitch that to him! We’d be fired. It’s insane. But when they come and they’re really willing to go hard with something and do things that are a little boundary pushing, it’s really exciting.
So people come into the writers’ room and interact?
For this one, I’m not sure if they actually came in person because now everything is on Zoom, but that’s how it used to be. For the Alec Baldwin roast, Caitlyn Jenner came in. Caitlin is an interesting person because she’s conservative and she’s trans. And she also claims she doesn’t have sex. There’s certain things that she’s very off limits about, but then there’s also some things she’s very open about. So you don’t really know what her sensitivities are going to be. We removed a joke about her having a dry pussy, but they had already sent it to her. When she came in and saw the script, she’s quietly reading and she goes, “Where’s the joke with my dry pussy?”
People’s skin is a lot thicker than I think people anticipate. Everyone just expects celebrities to suck. And one of the things that’s really exciting at roast is you find out that they’re a lot cooler than you thought they would be — or they’re as cool as you’d hope.
