Anthony Jeselnik on roasting, ripping off Jack Handey, and giving the devil his own TV show

Over the course of just a few years, Anthony Jeselnik has made an indelible impression as the dark prince of comedy, a strikingly handsome, charismatic, black-hearted joke-slinger with a genius for misdirection and quotably evil one-liners. Jeselnik’s star began to ascend with the release of his brilliant debut album, Shakespeare, but it really kicked into high gear when he began appearing on the Comedy Central Roasts.

Jeselnik’s appearance on The Comedy Central Roast Of Donald Trump was a star-making moment. The comedy-roast world had lost a giant in the great Greg Giraldo the year before, and Jeselnik helped fill the massive void left by his death. More attention-grabbing Comedy Central Roasts ensued, followed by the recent DVD and CD release of Jeselnik’s latest special, Caligula, and now his own Comedy Central vehicle, The Jeselnik Offensive, which traffics in the same whip-smart misanthropy as his stand-up; a memorable segment in the first episode features Jeselnik performing brutally funny jokes in front of cancer patients. The A.V. Club recently spoke with the comedian about his quest to write the perfect joke, why seemingly all of his friends and peers snagged Comedy Central shows at the same time, and why being a “Weekend Update” anchor would be his dream job.

The A.V. Club: What’s it like to be Anthony Jeselnik right now?

Anthony Jeselnik: It is exhausting. It is exhausting right now. I feel like I’m kind of learning a whole new skill. For the last 10 or 11 years, I’ve been getting as good as possible at stand-up, and now I’m trying to figure out how it can translate into a TV show like this. You’re learning completely different skills and figuring out that some of the things that help you in stand-up do not help you as a host. I’m relearning how to be on stage and talk to cameras and timing. But it’s fascinating.

AVC: Television hosts historically have had to win their way into the hearts of audiences if they’re going to allow them into their homes every night, whereas it seems like a lot of your act is about deliberately pushing audiences away, which has to create an interesting tension.

AJ: Yeah, I always thought so. I thought it was a different and interesting way to play it. People in the audience accepted it and went with it. I had to stand my ground until people got used to that, though. Now it’s my thing, where before people just asked, “What’s this guy doing?” I want to bring as much of that as possible to the show as a host, but I still have to be a host. I can’t just sit there and bask in an applause break on my TV show because it looks like I’m just waiting for five minutes. You have to keep things moving, but I still want to bring that attitude to the show.

AVC: You can’t be the prince of darkness and a genial host at the same time.

AJ: Well, I think I can. That’s my goal on this show. My overall conception of the show is, “What if the devil had a talk show?” But even if the devil had a talk show, he’d still have to be a little more charming. If I’m doing a Roast or I’m doing stand-up, I’m a blunt instrument. The idea is to beat these people over the head. On the show, you have to be more charismatic, a little smoother, but I think I can still be that prince of darkness. You just have to learn the tricks of the TV trade as well.

AVC: There seems to be an almost sadomasochistic element to your stand-up, where audiences like to be shocked and insulted and offended. They almost demand it. Does that put pressure on you?

AJ: It’s not so much pressure; you feel it a little bit. But the driving force behind doing everything that I’ve been doing for 11 years as a stand-up is having problems with authority and not liking to be told what to do. On Twitter, when someone would die, I would write a joke. Or if there’s a tragedy, I would write a joke and tweet it. That was my thing, and then at a certain point, people started demanding it. I’d wake up in the morning and people would ask, “Where’s your joke?” Someone asking for that kind of joke makes me not want to do it anymore. So it’s kind of a game for me to see how much I can play into it and how much do I take it in a different direction just to spite people, even if it’s my own audience.

AVC: Where do you think that contempt for authority came from?

AJ: I think just being a kid and not liking being told what to do and not seeing the point of stuff. I was just one of those kids who never understood why I should make the bed. Why should I make this bed in the morning when I’m just going to sleep in it at night? And I never got a satisfactory answer as to why I should do it. Early on, I just thought, “God, as soon as I’m 18 and I don’t have to play by these rules anymore, I’m going to do everything I can and dedicate the rest of my life to thumbing my nose at this.” And I’ve been able to do that and make a living.

AVC: Were you a funny kid? A class clown?

AJ: You know, I tried to be the class clown a little bit. At times I was guilty of trying too hard. It wasn’t until high school that I became more laid back about it. I always liked laughter and was interested in laughter. In the second grade, I would just get bored and a joke would pop into my head and I would have to say it. It was almost like I had some brilliant novel in my head that I had to get down, and I would interrupt class all the time and get in trouble. And then one day in second grade, I remember I made a joke. Some girl was moving to a different town and she was all excited, but it was a really bad place she was moving to and I made some sarcastic comment like, “Oh, well send us a postcard.” And the teacher laughed. And when the teacher laughed, she just laughed and kind of covered her face and then moved on and then I realized, “Oh, you can’t get in trouble if the teacher laughs. If you’re smart enough that adults gets it, you can get away with anything.” That became my goal as class clown: to make the teacher laugh.

AVC: Were you drawn to dark humor at an early age?

AJ: Absolutely. I loved trying to stay up late on Saturday nights to watch Saturday Night Live. There was something about having to stay up late and my parents didn’t approve of it that really attracted me. As I got older, there would be shows that I would discover that other people really weren’t into, like The Ben Stiller Show. On Monday mornings, I would come into school and ask, “Did you guys see The Ben Stiller Show last night? And no one knew what it was, but I thought it was the greatest thing ever. And then when I went to college, I was telling everyone they had to watch Mr. Show and nobody wanted anything to do with it. But loving that kind of stuff made me feel cool and special. Before I even thought about getting into comedy, I was drawn to that kind of dangerous, “We don’t want everybody, we just want our people” kind of thing.

AVC: What was your stand-up like at the beginning?

AJ: A guy in Santa Monica named Greg Dean taught a class. He had written a book, and when I first moved to L.A., I was working at a Borders Books and bored out of my mind. So I thought, “I’ll look at stand-up. I’ll see about that.” I looked for the thinnest book on comedy they had. It was about how to do stand-up, and at the end of the book it said he taught a class in Santa Monica. So I took it, and I’ll never forget my first attempt to do a real joke. You had to get up in front of the class and do seven minutes, and the first thing I ever tried was an impression of my dad being stung by like a million wasps that happened once when I was a kid. I remember just jumping around swearing and slapping myself. I stopped after a minute that felt like 10, and no one laughed at all. I remember thinking, “I will never do physical comedy again.” I thought I needed some other way to get into it, because this definitely was not it. Then when I first actually got on stage in front of a real crowd, I kind of just told a couple stories from when I was in college, some funny things that happened to me. My girlfriend had accidentally burned down my apartment my senior year, and I got fired from Borders. So I told stories about those two things.

AVC: Why did you get fired from Borders?

AJ: I was a terrible employee. I’ve been fired from almost every job I’ve ever had, luckily, in a good way, or else I’d be stuck. I’d still be at Borders Books right now. I would always joke around with everybody, and no one enjoyed my humor. Once you’ve stacked books all day, you never want to do it again. So I would just wander around looking at books and doing anything I could to not help a customer. Then I started coming in late and they said, “You obviously don’t want to be here. You’re gone.” But that gave me plenty of material, but after a while I got bored of telling stories. I only had the two stories. I was 23, 24 years old. And I wasn’t interesting.

I saw B.J. Novak one night at an open mic doing one-liners. And I’d always loved Mitch Hedberg and Steven Wright, but I didn’t think you could do that. So when I saw B.J. do it, I thought, “Oh my God, you can tell smart jokes like that.” That’s what I want to do. It made me think, “What’s the funniest thing in the world to me?” I’ll try to do that and try to find my own style, which I recommend to anyone in comedy. Anyone in any kind of art, the art world, does. Just try to rip someone off for a little while until you find your own voice, and for me that was Jack Handey with “Deep Thoughts.”

On Saturday Night Live, those pieces always killed me because there were so many levels to the joke, and it came out of nowhere. I thought if I could do something like that, it would make me happy. I started writing one-liners, but they were a little more bizarre. Then one day I came up with a joke with a dark twist to it. The crowd reaction was so huge that I had this light-bulb moment, this epiphany. I was about two years in at that point.

AVC: Do you remember what that first dark revelatory twist was?

AJ: Yeah, it was a joke that’s on my first album called “My Girlfriend Loves To Eat Chocolate.” I say, “She is always eating chocolate, and she always likes to joke she’s got a chocolate addiction. She’d be like, ‘Keep me away from those chocolate bars. I’m addicted to them.’ And it’s really annoying. So one day I put her in the car and I drove her downtown and I pointed out a crack addict and I said, ‘You see that, honey? Why can’t you be that skinny?’” And I remember comics just went, “Ooh!” and it was the best sound you could hear from a comic when you tell them a joke, and the audience was just screaming with laughter. I thought, “Oh, that’s all I have to do. Everything should be focused toward that.” I couldn’t have been happier.

AVC: You were getting the response you’d always sought.

AJ: Getting that response made things click for me. Dark humor appealed to me because it was a bigger laugh than you could get with anything else. Seeing people laugh at something inappropriate with their whole bodies, a guttural, visceral laugh beyond a mere “hah.” I thought, “If I can do that to people consistently in my act, I would be unstoppable.” It seemed like the way to go.

AVC: It’s interesting you mention Jack Handey, because his jokes are almost like haikus in their precision and their economy, which is not terribly dissimilar from your work.

AJ: Absolutely. I was obsessed with getting the perfect joke. Did you ever watch Fraggle Rock when you were a kid? I wasn’t a big fan of the show, but I remember seeing one episode where there was one Fraggle who didn’t have a sense of humor. He didn’t get anything. So he went and made a wish and somehow found the funniest joke in the world. Someone told it to him, and he didn’t get it. But he would tell the other Fraggles, and they could not stop laughing. It was like, “I’m going to kill everybody because they’re all just going to laugh themselves to death.” And he had to journey to find some way out of it, and I thought that that seemed to me to be the perfect joke. I thought, “Let’s try for that with every single one, to really swing for the fences.”

I thought a lot of that was the economy of words and getting the tightest, shortest joke you could. I was always cutting words. I even would write my jokes in my notebook. I still do this today, almost like a poem. Like a Jack Handey joke, where the pause in my delivery would be the end of the line because then I can look down, and even a joke that’s two sentences long might be eight lines in my notebook, and I can see exactly what words I can cut out and exactly how to make it as short as possible. Something about that really attracted me as a writer and as a performer.

AVC: Much more than most stand-up comedians, you seem comfortable with silence, with pauses. It had to be a little terrifying as a young comedian, deliberately going for long stretches of silence.

AJ: I just feel like silence is good. Silence means they’re paying attention. Even if I drop bombs and they’re dead quiet, it’s still okay. If they start talking, that’s when you’ve lost them. I want people to just be paying attention even if they’re not necessarily laughing at something, or if it takes them a while to get something, I don’t mind that. If half the crowd gets the joke and the other half is sitting there scratching their heads, that’s just as good for me if I like the joke, because I feel like it just brings people in more. I loved Dennis Miller when I was a kid. I loved the black-and-white specials. I loved him on SNL, and if you only got half the references, you still felt really smart. You don’t need to [keep] everyone entertained [for them] to still like you. I really enjoy those pauses and those awkward silences. It doesn’t play as well on TV as it does live, but I really enjoy them.

AVC: It’s also a form of control over an audience: “You will laugh when I allow you to laugh.”

AJ: It was important to me to be cool as a comedian. I didn’t want to be a crowd-pleaser who sent out the vibe of, “I need you guys.” I wanted to be so cool that the audience could leave and I would still be killing, that I didn’t want to have to rely on them or need them. That really appealed to me.

AVC: Most stand-ups are eternally seeking validation and approval, whereas you’re deliberately pushing them away.

AJ: Yes. Yeah. It’s fun to do. I have that need in me, I want everyone to love me, but I’m embarrassed by that need, so I wanted to cover it up in my persona. I felt like I wouldn’t be able to do stand-up for a career if I was needy. I didn’t want to be complaining or whining onstage. I wanted to be cool and do exactly what I wanted to do. That way I would never have to change for anybody.

AVC: How did you come to enter the world of roasts?

AJ: I always loved roasts. I remember watching it in college with my friends and thinking it was the funniest thing ever. Just watching people make fun of each other with these really smart jokes, and everyone was laughing and having fun and you could say things you couldn’t say otherwise. You could get away with things on a roast that you couldn’t get away with in stand-up, but I always loved them and thought that it was a format that was great well before I even thought about becoming a stand-up. I call roasts “The Super Bowl of comedy,” in that that casual comedy fans will all get together and watch a roast, whereas they won’t do that for stand-up or late-night sets or anything like that.

That had always attracted me, and I had always tried to get a gig writing for them. I knew I wasn’t going to be on them for quite some time, if ever, when I started out, but I thought to write for them would be great. And I finally got to write for them for the David Hasselhoff roast. Comedy Central brought me in for a couple weeks and it went really well, and they said, “We like you. We want to put you on the next Roast.” So I think before even that Roast taped, I knew I was going to do the next one, which ended up being Trump, and that was the biggest moment ever. I remember being so excited for that and knowing it was my big moment, that I didn’t want to blow it.

I wrote so many jokes for everybody. I was running them everywhere. It was fun to run them because I would go up on stage and I would say, “Listen, I’m doing the next Roast. Here’s the Roast jokes I’m going to try out for you,” and no one believed me. They thought I was doing a bit and said, “Well, you’re not on the Roast. We’ve never heard of you.” And when I got on the Roast, I remember just realizing halfway through the show, because I was going up late, that I was just so much meaner and harder than everybody else. My biggest fear was coming off weak or not strong enough, so I really overdid it and went up and just… that was one of my favorite moments of my life was doing that Trump Roast, because no one knew who I was and it just really caught everybody by surprise. And the next day, my life was completely different.

http://www.youtube.com/watch?v=lgdVpWeE0Ow

AVC: What’s the process of writing for a roast like?

AJ: As a writer, what you do is you come in and you write mostly for the celebrities or for the host and definitely the person being roasted. You don’t really write for the other comedians. You come in, and they give you assignments. They say, “All right, for the next hour, everybody write jokes about Pamela Anderson that anyone can say.” And then after an hour, they’ll ask, “Okay, now write jokes just that David Hasselhoff could say about Pam.” And then it’s, “All right, tell jokes that Pam could say about other people.”

You get your assignments to turn jokes in, and then they are all read on a big screen.

The head writer reads through them and if the room laughs, it goes in. If they don’t, then it’s gone. You keep doing that until you have a script ready for each celebrity, because a lot of people don’t want to do the Roast. You have to come to them and say, “Here’s what we’re giving you to say. If you think this is funny and you want to do it, then do it.” And that’s how we got Snoop, I think, on the Trump Roast. They said, “Here’s the script. We got you a really funny script. You should do this because we have this for you.”

Whereas, if they would have just asked him, he would have said no. When you can give them something, they’re always happier. But that was a fun time, because you’re writing for 12 hours a day with a group of people who are just the biggest assholes in the world, who write on these roasts all the time. I’ve never laughed so hard in my life. My head writer and executive producer on The Jeselnik Offensive is Tom Johnson, who I met writing on that first roast. But when you’re writing for yourself, it’s a little different. You find out the names; they’re adding names and subtracting names up until a couple days before the show. So the most stressful part is wondering, “Who do you have? Who’s the offer out to? Let me start working on somebody.” You have to make a joke about something everybody already knows about a celebrity. That can be tough, because you can’t go up there and say, “When you were in college, you studied this.” You can’t go too deep into Wikipedia. … For example, it’s a fact that Charlie Sheen shot Kelly Preston. He was playing with a gun or something, shot her in the arm, and they broke up. You could not make a joke about it because you would say it and the audience would think, “We don’t believe that, that’s too crazy.” No joke worked about that, which really fascinated me. So it had to be surface-level, but then you had to have a crazy twist on it.

AVC: With roasts, you have to make the obvious jokes, whereas your challenge as a writer and performer is to somehow transcend that.

AJ: Exactly. I just feel like I’m competing against the other comics. A person like Jeff Ross or Lisa Lampanelli or Amy Schumer or Whitney Cummings, who are going to have really smart jokes, too. You just want to have different smart jokes. You’ve got to go at least a little deeper than, say, Jon Lovitz or Kate Walsh would go.

AVC: Another challenge would be to write for someone like Mike “The Situation” Sorrentino, who is not exactly known for his comic gifts.

AJ: I was on that Roast, but I remember for him, it was a thing where he came on last-minute and a lot of the best jokes go to the first people on board. You need to get their script together, because if you’ve got a great joke it’s going to them. So he came in last-minute, and they thought they had good stuff on him. They really did. But it was stuff they wrote specifically for him last-minute, and he just did not know how to tell a joke. They had to work with him to say, “Here’s how you say this.” Then you get up there, and it’s like everybody has a plan until they get punched in the face. That crowd started booing him, and to his credit, he stayed up there. But it was not good. But he wasn’t set up to fail by any means. They want everyone to do well.

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AVC: It felt like that was the exact moment Sorrentino’s star started to plummet.

AJ: Sure, but it’s so interesting that it happened now, because if you watch old Roasts, there’s always these moments right before a commercial. They used to have so many people in the day, like 20 people up there, and most of them would never perform. You would just see, like, Big Pussy from “The Sopranos” in the corner just laughing. And then right before a commercial break, you would see Big Pussy at the podium telling a story or something. They would just do a couple seconds, and then get out. And what happened was he did a set, and it wasn’t that funny. So they protect him by showing him just a tiny bit. But now with Twitter—and it was really just literally Twitter—as soon as The Situation starts doing badly, everyone in that room is tweeting out that The Situation is bombing. They almost had to market the whole show based on that instead of protecting him and cutting him out or making him look better. They had to show him eating it. And that’s why I think the Roast has become a lot more difficult to do now. Most people don’t want to come on a Roast because they don’t want to be mean to someone else they don’t know. Now the fear is, “I don’t want to bomb. I don’t want to look bad because I know it’s a possibility, and people kind of almost want you to eat it on those things.”

AVC: What effect did the Trump Roast have on your career?

AJ: It completely changed my life. I had been headlining for about a year before that, but I would go to these clubs and people would be coming to see comedy. I’d have a couple fans from my album, which had just come out and who were there at each show, but mostly it was people who either got free tickets or got a deal. It was a tough slot to get through, because every time you began you wondered anew, “Are these people going to like me or not?”

AVC: You have to prove yourself every night.

AJ: Exactly, every single night. And then after the Roast, people knew who I was. I wasn’t selling out right away, but I was getting much bigger crowds and people just knew what they were in for, which changed everything for me. I got so much more comfortable. I could go a little deeper into my act and do things that I think are really funny. And the crowd, even if they didn’t laugh so hard, they enjoyed seeing me have fun. A lot of the jokes in my act are very similar to my Roast jokes, and after the first [joke] they’re thinking, “Oh you’re that guy from that Roast.” And then you do two and then you’re the guy from the Roasts. Doing two is the same as doing 10 in the public imagination. After that, you just keep on snowballing and you keep getting bigger and bigger. Now with a TV show, it’s a totally different world.

AVC: How did the television show come about?

AJ: I never really considered a sitcom. I thought that Comedy Central is a great place to be able to do whatever you want. I would love to do a network show at some point, but I knew that Comedy Central would give me the absolute freedom to do what I wanted. They believed in me and said, “If you’re going to do a show, just do a show you want. As long as you’re happy, we think it’ll be a good show.” At the time, I kind of got that deal right after the Trump Roast. They gave me this big deal to do an hour special and develop my own show with a pilot.

At the time, Comedy Central was looking for a half-hour to go on four nights a week after Colbert. They said, “Okay, this is what we’re interested in developing.” And they were developing with a lot of different comedians. A lot of people took a shot at this. And they liked the show. And [for] the show, I wanted to tell jokes. After writing on Jimmy Fallon for a year, I had a lot of ideas that they didn’t want or they couldn’t do in that format. But I thought if I ever had my own talk show, I would want to do this. I liked the talk-show format because it was this classic format that you could break out of. I wanted to do a monologue, but I wanted to do my monologue, the jokes that I would want to tell. I wanted to do like a weird kind of late-night desk-piece sort of thing that Conan would do, but I wanted to do my version of it. I didn’t really want to interview celebrities. I remember we had them for the pilot; I had a test interview. We brought in someone and I interviewed them, and I hated it. It’s weird for me to go from “I’m the biggest badass of all time” to “So tell me more about your movie. That sounds great.” I just didn’t have it in me. It was so wrong. It just fit me like a bad suit.

And I thought, “Enough of this.” I immediately knew and everyone was thrilled that I came to that conclusion after the first one. I love comedians, and I like all different kinds of comics. People think, “Oh, you must just like the dark guys.” No, I do dark. I like people who are silly and weird and people who are surprising and good at what they do. And when I bring on a couple comics and do a panel, [we] just more hang out and get weird and laugh together. So I decided just to have two comics on each show, because it takes the pressure off of one. Then people can relax a little bit. You try to get two people who are friends with each other, that helps a lot and just brings them into my world a little bit, but they don’t have to necessarily be dark. The stories will be dark, but they can be silly and weird and I can do my own thing. That really appealed to me. It’s the version if I had my own Late Night With Jimmy Fallon. This would be that exactly.

AVC: Are there any bits you might have pitched for Fallon but done on your own show?

AJ: I don’t think that we’ve done any of the actual bits that I pitched, but “Who wore it better?” from the first show was something that if I would have pitched on Fallon, they would have just stared at me. My specific job that was to do monologue. My favorite jokes never came close to being on, because they were jokes that were going to make somebody hate Jimmy. And I totally understood. I never thought he should be doing these jokes. I said, “This is what I would want to do,” and I couldn’t fake it. I couldn’t be like, “Okay, I’ll just write things that I think Jimmy will like.” I had to do what I thought was funny. One of my favorite things on the show was just getting to do my own monologue and talking about someone who killed themselves, or making a joke about some horrible tragedy—that I love, being able to fight for and get on TV. I just think it’s so different.

AVC: At the beginning of your career, it seems like you had more of an element of surprise, in that audiences didn’t know what to expect, they couldn’t see the dark twist coming. Now they do. Does that make your job a whole lot harder?

AJ: Yes, but I want it to be. I can’t just go out there and say something offensive or talk about something edgy without being able to support it with intelligence. It’s got to be either a good-enough surprise or a smart-enough take on it or something that you just don’t see coming. These days, during that pause, or before the punchline, everyone in the audience is trying to figure out what I’m about to say. And people are getting better at it the longer I’m around. Things that would have blown people away on my first album are now the norm on my second album. Not just with the show, but with developing my new hour, it’s got to be that much smarter. The bar is that much higher because people are starting to figure it out, and I need to stay one step ahead.

AVC: There’s a segment on the first episode where you perform stand-up for cancer patients. Some of the jokes are pretty harsh. When you’re doing something like that, is there some part of you that wants to pull a Don Rickles at the end and assure the audience that you’re really a nice guy?

AJ: No. I feel like that kind of ruins it. For me, whenever I see a commercial, where there’s some crazy-violent thing that happens, like two guys are talking about the new hamburger at Wendy’s, and one of them gets hit by a bus. You get that shock moment, and then right before the commercial ends, it comes back and the guy says, “I’m okay.” They feel like they have to do that to not upset people. That drives me crazy. I’m not an idiot. I know that this is a commercial and that somebody didn’t just get killed by a bus. In comedy, I hate that cop-out where you say, “Just kidding.” I know you’re just kidding. Don’t insult my intelligence by spelling it out for me that much. I think just by making them laugh and making a cancer patient laugh with an edgy joke makes me laugh. I remember going out to do that segment and we had talked about whether we’d get actors, extras, to pretend they were cancer patients, or whether we’re going to actually get them.

We decided for it to be real and not a case of us paying people. We put a thing out to a cancer support group and asked, “Would you want to come and do this?” And they said yes. They were excited about it. It started out awkward. But by the end, they were having a blast. I think they were just grateful that I wasn’t talking down to them. I said, “Here are the jokes.” People who have cancer never get to hear cancer jokes. They really had a good time, and afterward I talked to them for maybe half an hour and they were just thrilled to be a part of something like that. That was great. I had to fight with Comedy Central to put that on the first episode. They really didn’t want it on the first episode. They were like, “Uhh, I think the rest of the show’s strong. The panel’s so strong. Why not cut that out and just leave the full panel?” And I said, “Absolutely not. This is our first episode.” For me, it was like when Chappelle’s Show first came out. That first episode was really funny, but I’ll never forget the blind Klansman speech. That was one of the edgiest things they ever did, and they put it in the first episode. I felt like we were throwing down the gauntlet of what the show is going to be. And people like Jay Leno called me to tell me how much he loved the cancer segment. People really responded to that, and now Comedy Central’s like, “Oh well, we need more stuff like the cancer segment now.” And it was just something that nobody wanted for a while and now people really respond to.

AVC: That’s a little like when The Dana Carvey Show famously opened with Louis C.K.’s written sketch with President Clinton breast-feeding puppies. It was certainly a way of throwing down the gauntlet.

AJ: Yeah. I remember Louis C.K. drawing the line, and then whoever’s with us is with us, and that was what ruined that show. It was a huge mistake, but that’s a show on ABC starring Dana Carvey that people thought about very differently. I think that show probably could have survived a lot longer. I wish. I mean, it was such a great show. My expectations are way lower than Dana Carvey’s were. If my show got half the audience The Dana Carvey Show did, it could last forever.

AVC: With Adult Swim and FX and Comedy Central and HBO, this seems to be a very good time for weird, quirky fare on television.

AJ: For sure. And I think the people who want that, there might not be a lot of them, but they’re that perfect demographic for advertisers. You don’t need to get huge ratings if you’ve got the 18-34 male demographic watching your show, then you don’t need a lot of them. You just need to get a good concentration of them.

AVC: How much of your real self is there in the Anthony Jeselnik persona?

AJ: There’s certainly more of it in my television show than there is in my stand-up. I basically act like I’m the devil onstage. There’s not much of [me] in my stage persona, but a little bit is there, and the more of me that comes out, I think, just comes with getting more comfortable onstage and getting more experience with that. Ten years in, I’m certainly a professional comedian, but getting that 20-year mark, I can’t even imagine what my act will look like. It’s there. It’s like a suit of armor I put on. The more of my own self that comes out, I think the better things are, but it has to be natural. I like going up there like I’m Darth Vader and killing everybody. It just seems like I’m trying not to waste anyone’s time and just cut right to the chase. I think people appreciate that. But with this show, there’s a little more of me in there. There’s a little more of the guy who’s enjoying what I’m doing.

AVC: Is the persona constricting? Is there ever a part of you that goes onstage one night and just wants to spend 20 minutes talking about some shit you’re going through?

AJ: You know, I thought there might be. I remember when I was putting out my first album, I thought, “Maybe I’ll do this and then be finished with one-liners and just go on and talk about whatever I want.” But I hate that. I like being very efficient onstage, and if I went up and started talking about getting in a fight with my parents, I would just immediately feel whiney. I would feel like no one gave a shit, because if I was in the audience, I don’t ever care if someone’s talking about their life like that. Unless, like, if Louis C.K.’s talking about his daughters, I’m on board. He’s brilliant at it. But I wanted to be brilliant, too, and the only way I can be brilliant is by doing what I’m doing now.

It wouldn’t be satisfying to me to talk about myself like that onstage with my real personality, when I feel like I can present these jokes. And then it’s fascinating to me not just to present jokes, but to be able to pace that for an hour and have everything run to the persona. I’m fascinated by this character I’ve created, and the jokes I can come up with. That just becomes the challenge for me instead of trying to get more open and real onstage. That doesn’t appeal to me at all.

AVC: It seems like a lot of your friends and peers are getting Comedy Central shows at the same time—Nick Kroll, Amy Schumer, Key & Peele, Jeff Ross. Is that a coincidence, or do you think you’re all riding the same cultural wave?

AJ: I think it’s a couple of things: I think it’s partly coincidence. But I think Comedy Central’s just gotten bigger and they’re figuring things out more that they have to give shows more room to breathe instead of canceling things right away. They’re finding comics they believe in and giving them total freedom and then seeing what works. I think that they’re giving more and more shows a second season right away without just canceling them immediately if they believe in them. And I think with the Roasts, I think a lot of it happened because of Whitney Cummings. I think that Whitney became a huge star after that Roast and Comedy Central let her get away, and now she’s making a ton of money for NBC, for CBS, for E!, and they just really felt like, “We blew this.” Now when I came off the Roasts, “We’ve got to tie him up. We’ve got to tie up Amy. We’ve got to.” And the only thing they really have to offer— because they don’t have the money—is to say, “Here’s the freedom. Do what you want.” And since [they’ve] given you such a high profile from the Roasts, they almost have to put you on the air. So this is my first pilot I’ve ever done. I know it’s the first pilot Amy’s ever done. And they picked them both up. They are putting a lot of weight behind us because they’ve learned from their mistakes. It’s almost like a brave new world for Comedy Central. I’m so glad that I have this show now as opposed to even a couple years ago, where I don’t think they would have given me nearly as much rope to try to hang myself.

AVC: Did you watch the Academy Awards?

AJ: A little bit. A little bit. I kind of just watched it to see Seth. But I thought he was great.

AVC: When you watch something like that, are you watching it with your writer’s eye, thinking how you would do it?

AJ: Oh, yeah. It’s impossible not to imagine it while you’re watching it. I never go see live comedy shows because I just sit in the audience thinking, “Here’s what I would say. Here’s what I would do if I got up there right now.” It drives me crazy. But I don’t know. It’s a very thankless job hosting the Oscars, but I would never turn it down. It seems like and I’m sure Seth is thrilled that he did it, but that he never wants to do it again. About that, I thought he was phenomenal. I thought he really brought himself to it and just did his version of the Oscars, which is all you can hope for. I’d certainly rather watch him do it and watch the audience kind of turn on him and come back than watch Anne Hathaway and whoever the hell else hosted the year before. That was bad.

AVC: That would be James Franco.

AJ: Yeah, James Franco. That was awful. I just want to see something interesting, and he certainly brought it.

AVC: You mentioned Dennis Miller before. It seems like your persona would be ideally suited to being a “Weekend Update” anchor, since they kind of have permission to be mean and aloof. Is that something that would appeal to you?

AJ: Dream job. Absolute dream job. Always has been. I would give away everything that I have to be a “Weekend Update” anchor, and I don’t think it will ever happen. It’s one of those things that would have been my dream job, but as I was coming up, SNL never called me. They never asked me to submit a packet or come on board, and I think they’ve gotten away from having stand-ups on the show. I think probably Norm Macdonald was the last pure stand-up they had. I’ve always told agents and managers if that job is ever in play, I want to be in the conversation, even if it’s just to have my name brought up in the room. But I would throw everything away to be the “Weekend Update” anchor.

AVC: Just so you can have an awkward conversation with Lorne Michaels you could tell your grandchildren about?

AJ: I actually got to meet Lorne when I was on Fallon for one of those 10-minute meetings, where it was me and the rest of the monologue team. It was one of those meetings where you’re very aware that you should not say a word, but he said a couple things in there that I’ll never forget, that are just these comedy nuggets that were so great that just stuck with me forever. I don’t think there’s anyone more knowledgeable about comedy than Lorne Michaels. It was really interesting.

AVC: Was there anything in particular that stands out that he said?

AJ: There were two things he said: I remember one was just talking about jokes. He was saying that in a late-night monologue, it’s not just about being funny; you have to come off as knowledgeable. You have to cultivate a persona of trust and intelligence and likeability. I remember a specific example was, if you make a joke about a retarded person, the audience might laugh, but as soon as they’re done laughing, they don’t like you. And you’ve got to worry about the long game and not just that five-minute monologue in tonight’s show. You’ve got to worry about the next 15 years. That really stood out to me. And he said something about how—this was right before they announced Jimmy Fallon for the show—critics had their knives all ready and we knew that people were going to be coming for us right off the bat. He said, “Don’t worry about that. With a show like this”—and I think he referenced Conan specifically—“the longer you’re there, the longer you’re there.” So when your TV show comes out, everyone attacks it because it’s something new and they want to compare. And I’m seeing that now. It’s like, “Oh, you’re just trying to be like Tosh. Or you’re just a rip-off of The Burn [With Jeff Ross].” Or, “You’re trying to be like Dane Cook.” I get all these different things, and it’s just people who feel the need to attack something new and different. After a season, after a year, after six months, you’re just there. You’re just there every night. And no one would ever think to make fun of Jimmy Fallon now, because it seems like he’s been there forever. He’s just part of the TV landscape. You just have to take your lumps and just keep on churning it out. Eventually you’re a cultural institution. That’s just a good way to look at things.