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Anthony Jeselnik and Pete Holmes.

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Pete Holmes Interviews Anthony Jeselnik About The Jeselnik Offensive and Dark Jokes

Stand-up Anthony Jeselnik doesn’t worry about what's taboo; in fact, he jokes exclusively about those things that other comedians might consider off limits. We saw this in his Late Night and Tonight Show sets, his Charlie Sheen and Donald Trump roasts, and his hour-long special Caligula. Now he's bringing his dark sensibility to The Jeselnik Offensive, his Comedy Central show premiering tonight at 10:30. (It's formatted like a late-night show, only in his version of the classic “Who Wore It Better?” trope, for example, Jeselnik compares President Obama's hat to the Virginia Tech killer's.) To best understand Jelesnik, Vulture got him on the phone with one of the silliest, most positive  stand-ups working, Pete Holmes. (Holmes hosts the very popular podcast "You Made It Weird" and is developing a late-night show with Conan O’Brien.) Here's how their conversation unfolded.

Pete Holmes: What’s going on? That’s my first question. What’s going on?
Anthony Jeselnik: Not much, man. Just finished editing the first episode. We taped on Thursday, and we’re getting ready for the premiere. 

Is that right? Who are the guests on your first show?
Amy Schumer and Aziz Ansari. 

Nice. Who did better? [Laughs.]
They both did great. That’s an unfair question. 

I believe you, I believe you. Did you consider having me as the first guest?
I did, I did, but the higher-ups of Comedy Central said it wasn’t a good option: “How about someone, you know, a little more well-known, a little funnier? Someone who could think on his feet?” It wasn’t an insult to you. It’s just a very realistic way of looking at your career.

[Laughs.] Pragmatic, really. I’m going to try and keep the interview as much about myself as possible. Do you think I’ll enjoy the premiere?
I think you’ll love it. Once you get past your jealousy, I think it’ll be really fun. We talk about things that no other show would talk about or make fun of. Anyone can enjoy it even if they’re just enjoying the balls of it all. 

Is that kind of what the show is? I know it’s The Jeselnik Offensive. Is it offensive?
When I came up with the title The Jeselnik Offensive, I thought of it more as a militaristic thing. Like the Tet Offensive, we’re coming at you, we’re being aggressive. A lot of these shows — shows that I think we both have worked on — so much of it is making characters likable or making the people you’re writing for likable. I don’t have to worry about that. Let’s just do what we think is funny and worry about the complaints later. We want people to complain. 

You’ve managed to do that. Look, I’m going to pay you a compliment. There are a lot of comedians that talk about taboos and things you’re not supposed to talk about, but what you’ve done is managed to remain impossibly likable through the whole thing. I know you’re a really sweet guy, but even if you’re Jeselnik onstage and you’re doing abortion jokes or whatever, people are still rooting for you and loving you. Is that something you feel like you’ve accomplished on the show as well?
Yeah, I definitely think so. A lot of that just comes from my own personality. You see my joy in what I’m talking about. I think I get away with it onstage because I come from a different kind of place. I’m not the voice of reason; I’m more the guy using these offensive topics as fodder to raise tension in a joke. 

And it is true. I think if shoplifting were a victimless crime, it’s almost when I watch your comedy, it’s like you’re inviting us to do some light shoplifting with you. [Laughs.]
Exactly. Everyone has the same kind of fears; everyone has the same big problems in the world, which is like fear of death and “I hope horrible things don’t happen to my family,” but they do. And I think people laugh at them as this great release. 

So, what was it like being a boss? Do you enjoy being the boss of the show?
I really do. I learned about being the boss from working at Late Night with Jimmy Fallon and seeing Jimmy be the boss and seeing the way he handled people. But I think not just from seeing Fallon but also starting out in this business as an accounting clerk and an assistant on TV shows. Being in the lowest rung of people, where no one knows your name or respects you, to eventually being a writer, to eventually being the star of the show, I know how everything works.

What would happen when a joke of yours would get rejected on Fallon?
On Fallon, we would have these pitch meetings. And every single time I would pitch, it would be the biggest disaster of all time. Some of the writers would laugh, but Jimmy would always stare at me as if I was trying to make fun of him, which I wasn’t at all. The producer said to me a couple times, “Listen, we all know you’re funny, but these bits you’re pitching, they’d be great for The Anthony Jeselnik Show, but they’re not right for The Jimmy Fallon Show.” And after a couple times hearing that, I was like, “God, that Anthony Jeselnik Show sounds really funny.” So I decided to make that show. One of the greatest strengths of the show is that I know you won’t see any of this stuff on something else.  

This is not Chelsea Lately.
No, I have a joke where I go, “Welcome to the panel. The panel that’s just like Chelsea Lately, only better, because are you fucking kidding me?” That is almost the mission statement of the show. 

So tell me a little bit about the show. You have panelists on and you talk about news items that maybe other shows aren’t covering.
Sure, I wanted it to be my version of a late-night show. Pretty much all the things that I couldn’t do on Fallon, I get to do on my own show. So I come on and I do monologue jokes about things that you wouldn’t even think as a topic to do a joke on. Like, we have a joke about this guy on Storage Wars who killed himself. That’s the setup of the joke; we make fun of that. No other show would ever do that joke. I’m like, “Oh my God, this is so perfect.” And we have what we call in the business a desk piece, like something Conan would do, either at a desk or standing there — just a random comedy piece but just much, much darker than the normal show would be. Then we go to commercial, and when we come back, we either have a shorter bit or a longer piece we call a Sacred Cow. We take a subject that people usually don’t find funny or that you can’t make fun of and do a whole bit making fun of it. In the pilot, we chose cancer. I go talk to an oncologist and I make fun of her and make fun of cancer. At the end, I go to a cancer support group and do stand-up for people who actually have cancer. People get offended by cancer jokes, but cancer patients don’t ever get to hear them.

What it sounds like you’re doing with your show is letting people in on the sort of jokes that we don’t normally get to see. The hardest laughs comedians have backstage come from making cancer jokes. You’re bringing that to the show.
Comics always hold things back. And I thought, Why keep that away from people? I like seeing what the comedian thinks is funny, not just what they think I’ll think is funny. 

We did the pilot together, but I understand the show’s changed a little bit. Before it was everyone trying to do your voice and be darker, but now you want people to do their own thing.
It’s very much everyone does their own thing. It’s always funny if someone does darker stuff, but I’m the dark one, so I want people who are so different from me. Like, we’ve got Kristen Schaal coming up on an episode, and Billy Eichner, and they couldn’t be more different from me, but I want them to be able to come on and do what they do. 

Honestly, even though I think it’s so fun to have someone like Kristen Schaal on the show, who is so different from you, I have to imagine in the safe space of The Jeselnik Offensive that she’d probably be more comfortable letting those colors show. You and I both know that the sweetest comedian can have some of the meanest and most hilarious sense of humor offstage.
Yeah, and I think they’ll have that opportunity because we’re talking darker and weirder stories. I think it’s hilarious when Kristen Schaal occasionally says something biting, but I also want them to feel free to just be absurd. A lot of the panel is just really absurd, weird things. Like, we’ve got a bit called Latino Voices where I ask the panelists questions in a Latino accent, and they respond in a Latino accent. It sounds like it would be an offensive, awful thing, but to watch Aziz make the decision to commit to the bit and do this accent that he knows is offensive and almost hates doing it is great television. 

Yes, yes, yes. So Aziz can stop doing his Ross Perot impression.
[Laughs.]

It’s so funny that there’s that caramel swirl of silliness in your dark-chocolate ice cream. That to me is what makes you work and what will absolutely make the show work. It’s like we’re in Jeselnik’s basement. We’re in high school and we’ve just kept ourselves laughing all night, like playing video games and watching movies and just joking around. It’s dark but it’s still our friend Anthony.
Yes, I feel like the entire audience is a bunch of little kids tied up in my basement.

[Laughs.] Will you please do the joke I wrote you on your show.
Of course. And you didn’t write it for me. You wrote it, decided you were too pussy to do it, and then tried to give it to me. Don’t feel like I inspired you to do it. 

That’s exactly right. I wrote a joke that was very funny but it was too mean, so I gave it to you and you were like, “I don’t do other people’s jokes.” But that’s exactly the whole point of the show, to be like, “Why not just do that joke?”
Well, when I have you on, when you’re part of the panel, we can bring that up in the interview part of it. 

Oh my God, I would love to give that joke a home. 

Photo: Getty Images, Comedy Central