Anthony Jeselnik Is Evolving. But He’s Not Losing His Edge

The provocative, brilliant stand-up talks to Cracked about the character he plays on stage, Donald Trump, Norm Macdonald and his great new special ‘Bones and All’
Anthony Jeselnik Is Evolving. But He’s Not Losing His Edge

When Anthony Jeselnik logs onto a Zoom chat to discuss his cutting new special, Bones and All, he does something I wasn’t anticipating: He smiles warmly. 

Fans of the 45-year-old comic have come to expect a certain onstage demeanor — that combative expression, the precise delivery, those straightforward setups about family members and loved ones that lead to horrible, surprising, utterly killer punchlines. Jeselnik is celebrating 20 years in stand-up, and by now most everyone knows that the person we see up there telling jokes is a character — an abrasive, sometimes obtuse jerk who shocks us with his nonchalant tales of dead grandmothers and abusive fathers. We realize that the real Jeselnik knows that it’s not good to drop a baby. The actual guy never took his self-proclaimed chocolate-addicted girlfriend to meet a junkie so he could ask her why she’s not as skinny. Still, the pleasant man I see contentedly sitting in his L.A. kitchen is the one we don’t encounter as often. 

Jeselnik still has that edge, though. It’s the week before Bones and All’s November 26th debut on Netflix, and during our hour-long conversation, he makes it known that, yes, he thinks he’s a better joke-writer than his peers, although he does have sympathy for younger comics who have to keep producing new material to gain a following. “There are too many specials, but that’s not my problem,” he says about the glut of comedy sets on Netflix, Hulu, Prime Video and YouTube. “I look at kids now who have to film all their sets, and it’s all crowd work — I’m so glad I don’t have to do that. It used to make me mad, and then I realized I’m just old. If I started out today, I’d be doing that same thing. I don’t know if I’d even want to be a comic, but that’s just the way the business is now.”

It has been five years since Jeselnik’s last Netflix special, Fire in the Maternity Ward, a title that speaks to the gleeful provocation of his material. (That’s the special, you may remember, where he tells a detailed, brutally funny story about taking a friend to get an abortion — the baby wasn’t his — that’s partly about his annoyance that people sure get uptight in those waiting rooms.) Back then, his hair was short on the sides and spiky on top — plus, he had a beard and a leather jacket. In other words, he looked like an asshole, which played into the character’s DGAF mindset. (In the Netflix artwork for Fire in the Maternity Ward, Jeselnik is literally sneering.) 

But for Bones and All, there’s a notable change in his appearance. The hair is longer, looser. Jeselnik isn’t dressed like he just showed up on his motorcycle. And while the humor remains dark and daring — the ingenuous misdirections of his punchlines still able to give a viewer whiplash — it’s never been clearer that the character is just a character, and that its creator is using it to challenge and surprise his audience in exciting new ways. After 20 years, Jeselnik is continuing to reinvent and reconceive his onstage persona in order to keep his fans off balance.

“Even in my set now,” he says, referring to the material he’s developed since Bones and All — a special based on jokes he’s honed on tour over two years — “if there’s one joke that’s just way too hardcore, that’s okay. I just don’t want to do a set full of that. But it’s nice to know that the audience thinks that could happen at any time.”

Not that you’ll watch Bones and All and think that Jeselnik has “mellowed” or “softened.” The character remains a real piece of shit. But as a risky opening bit about trans people (and an audience member who finds those jokes “problematic”) proves, Jeselnik wants to use this fictional alter ego to question the state of modern comedy — a place where, for some reason, it’s acceptable for stand-ups to punch down at the most vulnerable communities. 

His jokes are scathing, but the targets are the ways that privileged stars like Jeselnik (but not Jeselnik) think they should be allowed to say whatever they want on stage but then cry “cancel culture” when someone criticizes them. Over the course of his five specials — starting with 2010’s Shakespeare — he has gone after what we find too sensitive or too taboo and then figured out how to make us laugh. Bones and All is his most “mature” work, even though the character is now fatally poisoning his siblings and watching porn at the most inopportune moments. As for the trans bit, it’s great while permitting the character an opportunity to talk about how much he hates pregnant women. (Yes, the character hasn’t stopped absolutely despising kids.) 

How much of the character is Jeselnik? Are any of these jokes based on actual events? He and I talked about that — and also what he thought of Tony Hinchcliffe’s notorious Puerto Rico joke, the problem with podcasts and whether Donald Trump is actually funny.

The material in Bones and All is something you’ve developed on the road for a long time. Now, the special is coming out in a week. How are you feeling? 

I feel great. It’s a weird place to be in because I did tour this for two years, I recorded it in April. I’m one of those guys, you could either watch your special a million times and edit and perfect it, or you can watch it twice and say, “Get the fuck out of here, I can’t (look at) it again,” and I’m the latter. 

I’m mourning that I can’t do these jokes anymore. I just had a great run in Europe that was so much fun — the international part was great — and after two years I’m sick of the jokes but, also, I’m going to miss them. I’m excited for the special to get out there and see what the public thinks. Doing this show for two years, it’s people buying a ticket and coming to see it, but when you’re just clicking on Netflix and you don’t give a shit, that’s when you really find out how good it is. And I’m excited for that. I’ll find out if I’ve ruined people’s Thanksgivings. (Laughs) I can see a lot of people being like, “I watched this with my parents and it ruined Thanksgiving” — then I’ll know it’s a successful special.

After 20 years of touring, are there people who come to the shows who don’t understand what you’re doing? 

Occasionally, yes. But at this point… Lorne Michaels once told me — he was talking about Conan and his success — “The longer you’re there, the longer you’re there.” So, just by doing it for 20 years, everyone knows now. It’s very few people who really think that I’m a monster, and if you are, you’ve been living under a rock. My comedy is more accepted than it’s ever been, just through virtue of being around long enough for people to understand what’s happening.

How does that change the level of difficulty for you? People go in expecting that edge and that darkness. Is there a pressure in figuring out how you can keep it fresh?

It’s certainly a challenge, but in every challenge there’s an opportunity. It’s “Where do they think I’m going?” You’ve seen the special, the bit about gallows humor only works if you’ve seen Thoughts and Prayers and you think you know where I’m going with that. There are opportunities in this long career I’ve had, and all the negatives — “Oh, they’re familiar with you, they know what you’re going to do” — those are all champagne problems. There’s a lot of comics who make it five years who never have to deal with this. I’m not going to complain, but it’s certainly in my mind when I’m writing new material: “They have five hours to go on, how do I still surprise them?”

The bad version of the comic you could have become would have just thought, “Okay, I’m just gonna go darker and darker and see how much more I can push this.” So how did you navigate how to be this character once the initial novelty wore off?

The audience tells me what works and what doesn’t. There are plenty of jokes where I’m like, “This is obvious,” but that’s just because of the way my mind works. The joke about my family being addicted to pornography and being at a reunion (in Bones and All), I asked a friend, “Is this obvious?” And they’re like, “No, only to you would this be obvious.” So, it really is a conversation with the audience because something that’s obvious to me is not to them — and vice versa, where I think this joke is brilliant and they’re like, “No, no, no, we saw that coming a mile away.” 

To keep going darker and darker, that would be serving one segment of my fan base who was always going to complain that the first album was the best, was the most shocking. I’m not going to be a slave to my audience, ever — I will not do that. The only way to get through it, instead of going darker, is to become more clever and to become a little bit more flexible. Things that you think are going to go dark, they end up going more silly. And I think that’s where my future lies — in the silliness, in trying to come up with longer-format narrative, in order to hide the punchlines. Just going dark, I’m too old for that shit. I loved it at the time, but people rank my specials much differently than I do. A lot of the OG fans love the original: “I can’t believe you just tore off a baby’s head!” I like the more subtle, I-still-got-you-there kind of thing.

Fans don’t go to your shows expecting to find out what’s really happening in your life. There’s no consistency to the character’s family or anything else. 

I love that it doesn’t matter. The character is so fully formed, and you’re in good hands where, if it’s a lie, it’s a lie throughout the hour — I’m not pulling the rug out from you, being like, “You’re an idiot for believing that.” 

But sometimes, I do wonder if anything is based in truth. Like, did someone actually confront you about your trans material being problematic, as you describe in Bones and All?

That actually is a true story — I make it (sound) that it was the week before, but what had happened was, I had 15 minutes of new material before the pandemic hit, and that trans bit was the closer without the story around it. For a year, I didn’t do anything — I didn’t write, I just tried to stay sane and get a dog. My first show back was an outdoor show after I got vaccinated, and a trans comedian came up to me — in the bit (in Bones and All), I don’t (identify the person as) trans because that would make it too much of a thing. But a woman came up to me and said, “I know you don’t think that’s problematic, here’s why it is. I can tell you think it’s a pro-trans (joke)...” I was annoyed — like, “How dare you?” But on the walk home, I was like, “How am I going to use this?” And by the next night, then it was my opener, and I had the whole story, all of it mapped out. So, it is based on something, but it happened before any of the tour started.

Did you ever thank the trans comedian for the tip? Have you seen them since?

I talked to them since, but it was when they saw the bit. I got offstage and they were like, “Damn, you really roasted me, but the joke is no longer problematic.” If I thought the joke was problematic at all, I never would’ve done it, but to hear that it became less so — and it became more of what I wanted the bit to be — was great. I may have said thank you, but if I did, I said it sarcastically. Like, “Even though you helped me out, leave me alone.” (Laughs)

What’s that process like of going from being pissed off initially by feedback to getting inspired with a new, better idea for the bit?

It’s like “How dare you?” and then, “Oh, this is an opportunity — don’t throw away this opportunity because of your ego.” I talk about opportunity a lot: How do I subvert? How do I change someone’s mind? How do I do anything? P.C. culture is the norm and that is just full of opportunities — it’s not a dead end.

That attitude must be something that developed over time. I don’t imagine, as a young comic, that desire to embrace the opportunity happened as easily. 

It’s always hard, I never want to be told what to do by anyone. Even if it’s Chris Rock — he’s like, “Hey, I’ve got a bit for you,” I’m like, “Get out of my face, I want to think of it myself, that’s the fun part.” 

I think in the beginning, (that kind of criticism) would’ve affected me more because I had less confidence. Now, after doing five hours of comedy, it’s like, “Oh, I know.” But in the beginning, unless it was someone I really respected, that probably would’ve hurt my feelings. I don’t know if I would’ve seen it as the opportunity it was. For the most part, if you hurt my feelings and I can find a way to turn it into a bit, I’m going to do that just to make myself feel better. The Norm Macdonald story at the end of the special is me making myself feel better about taking an opportunity to work with my idol (on Last Comic Standing) and having it be a huge letdown for both of us. That was a difficult job for me, and I feel like I got it off my chest doing the special.

The Macdonald story is great in Bones and All. But in real life, was it a combination of sadness and anger that you too weren’t gelling on Last Comic Standing?

It was anger, but it wasn’t anger that we’re not gelling. It’s Norm’s a difficult person, I’m a difficult person — it’s not crazy that we’re not gelling. Honestly, it’s almost an honor — it’s like someone telling you you remind him of your dad. But Norm and I were both very angry that we took the job — we were mad that we had to be there for the amount of time we had to be there. We thought we were getting into something else, and so for those eight episodes, we weren’t mad at each other, we were both just mad. And when we butted heads, it was a lot. We both had wished we had gone back and not taken that job.

What makes you a difficult person?

I’m not the friendliest. You can work with me and think, “He was totally professional, he was great, but I don’t really have a sense of who he is. We didn’t really hang out.” I’m not trying to bond with everybody — let’s just be professional and do our jobs. People who are on the road with me are like, “He’s professional, he does his job, we don’t hang out much.” But I’m not mean. Norm wasn’t mean — he was just aloof, and when you’re trying to go and connect with that, it becomes difficult. And when it’s two of us going back and forth on stage, I was looking forward to it and he was not, and that was difficult.

What’s that about, this desire not to hang out when you’re working? Are you somebody who’s more introverted?

I’m more of a writer than I am a comedian in terms of temperament, in terms of behavior. There’s a lot of comedians whose set is the least important thing of their night — it’s the hangout, it’s who you’re going to go see, “We’re going to go to this other club and go watch someone’s set.” I’m not doing that — I’m never going to do that. I’m like, “I’m going to do my work and go home” — that’s the job to me. The fun part is the writing, it’s doing the act. Even before I stopped drinking, I was never a go-out (person). I don’t want to meet people after the show — I want to go back to my room, relax, read a book. That’s the job. 

Is there any ideal scenario for you in the future where you’re just writing the jokes but not performing? 

I love being up there, obviously. There’s an adrenaline that comes from that. Also, these are my jokes — most people wouldn’t tell them. Not just wouldn’t tell them the way I tell them — they wouldn’t tell them at all. 

Early in my career, if Sarah Silverman had said, “I want to buy you for life, just write jokes for me,” I would’ve happily done that. Watching her tell my jokes, if I thought a joke was great, Sarah Silverman always thought it was great. Jimmy Kimmel always thought it was great and did his best to do it. I would’ve been happy writing for them, for a while anyway. This was in my 20s when I wrote for them — jokes here and there — but I enjoyed that. When you got into Jimmy Fallon — and this is not a knock against Jimmy Fallon, but Jimmy Fallon couldn’t tell my jokes, he wouldn’t have the job he has today if he had told any of them — in that case, I was like, “Well, I have to go do this.” (Editor’s note: Jeselnik was hired to write on Late Night With Jimmy Fallon in 2009.) That kind of (writing) job, where it’s “Hey, this is funny, but we can’t use it,” that kills me. So then I have to do it myself. 

I hate the travel. I hate the sound check. But I love being on stage with 1,000 people who were there to communally laugh at this darkness — that’s something that I’ve grown into and that I wouldn’t want to give up.

Comics get tired of being asked, “Hey, now that Trump is back in office, does that make your job easier?” But because your humor leans toward the darker aspects of life, is there an element of us hurtling toward national and global disaster that plays into your style? 

I could be wrong about this, but I believe that most of my audience who buys a ticket — not just watches on Netflix or listens to the podcast, but who buys a ticket — are conservative people. My family are conservative people. I’ve got no problem with that — if you’re wearing the fucking hat, then it might be different. But if you just voted for the guy, I’m okay with that. It does make it a little easier in terms of people laughing at the dark stuff — my (conservative) audience thinks, “Well, we won, we’re not mad. We’re celebrating, so we can laugh at all this stuff, that’s fine.” 

When Trump got elected the first time, I had a TV deal on Comedy Central to do a weekly show talking about the news, and I said no, and they couldn’t believe it. I was like, “Watch, everyone who does this is going to embarrass themselves,” and that’s exactly what happened. You had a couple people come out of it unscathed, but for the most part, it was humiliation. Everyone was doing the same jokes, and I wanted nothing to do with that. Whereas, if Hillary had won, I can be the evil character — Jordan Klepper’s show was supposed to be an evil version of The Colbert Report, and then evil shit started actually happening and they had to abandon all of that. But as far as stand-up, it’s just more opportunity for me, having Trump in office. I can start sentences differently than I would have before, but nothing changes for me.

Obviously, you don’t like Trump. But do you think Trump is a funny person?

I dislike his hypocrisy. I dislike his personal greediness for his own wealth. But I think he is way funnier than anyone gives him credit for. In these speeches, these rallies he’s doing, which I’m not a fan of, I don’t think he’s even trying to be funny — I think (it) just happens to come out. If he wanted to be funny, he can be.

I remember doing that roast, someone’s doing a joke — they kept saying, “Winning,” it was right after Charlie Sheen had done the “winning” thing, and people kept doing it. It’s done five times throughout the roast, and then Trump does it, a joke kills, and he goes, “Winning,” and they laugh, but a little bit less, and he goes, “I think that’ll be a little less funny in two weeks, no?” He knew it was airing two weeks from now. I’m like, “Oh, you’re smarter than all of this.” I think he is legitimately funny, yes.

Being part of the Comedy Central roasts was a big boost to your career early on. Were you roasting your friends as a kid?

I think all kids are roasting friends, and those (celebrity) roasts had started to air around that time that I was in high school or college. I wanted to be on a roast more than I wanted to be a stand-up — my jokes were like, “Hey, roast, notice me.” But, yeah, we were very roasty with our friends. It was the kind of thing where you would roast and we’d be laughing, and then when you told a bad roast joke that made no one laugh, that would be the funniest one of all of them, and then you would move on. 

Growing up, were you the funny friend?

I was among funny friends, and when I’m starting out — maybe 10, 11, 12 years old — I’m the unfunny friend of the funny older brother. That’s who I looked up to: “If this guy in high school thinks this is funny, great.” And then as I started to get into high school, making kids my own age laugh — and then making older kids laugh — was huge. And by the time I got to college, there were three of us — Gregg Rosenthal, my best friend to this day, was one of those, we were neck-and-neck — and then I just went professionally and they became normal people. But they were all still funny, nothing changed, I just kept on trying to go deeper.

Even back then, did you think of your comedy as performing as a character?

I thought of it as a character — I think other people did not. (Laughs) They were like, “You’re just mean” — it was so mean that some people laughed but were more afraid of you. I think I probably wasn’t that pleasant to be around in college, after college, because I was always going for the joke at someone else’s expense. Now, I’m a little more savvy. I know how to be a little more charming and make fun of the third thing (about you), if you will, but I can absolutely just go right to someone’s face. But I thought of it as a character. I think a lot of people now, if they make a mean joke, (they’re) like, “I was just joking” — what they mean is “I was in character,” but the character’s not performed well, and you still hurt someone’s feelings.

Authors and screenwriters sometimes create backstories for their characters, even if we never learn those backstories, just so it’s clear in their own minds. Does your stand-up character have a backstory? 

I love a no-backstory villain. I love “We don’t know what’s happening here, we don’t know what their problem is.” My character was like the devil’s son — it was like Jesus Christ as the devil, where there is no motivation other than just being evil. I didn’t want to get into “Here was my upbringing — if I had had a better babysitter, maybe I wouldn’t be like this.” I wanted none of that, because that stuff always sucks. You don’t know why I’m like this — you don’t have to know — and I love that. I’m very interested in villains, and what makes someone a good villain — a lack of an origin story is always preferable to me.

Every new hour, I can resurrect everyone. The mom dies in the last special, she’s back alive now. I’ve got five brothers and sisters, now I’ve got one, (now) I’m an only child. The audience doesn’t care. They recognize me, but they’re just in for the story — it doesn’t really matter what’s true and what’s not. And I don’t write a whole new hour until the special hits, because I don’t want any of that old stuff in my head. I don’t want to think about the grandma I killed or the grandma who is still alive — let’s just go from scratch and do it that way.

Other comics joke about their personal lives. You don’t — or maybe you do, but it’s woven in there so deftly that we don’t know what’s real or not. Are there parts of you that are actually hidden in those jokes?

Not at all really. Maybe in terms of my morality — I think you can probably get a sense of what I think about the trans issue. I think you get a sense of what I think about pro-choice or pro-life. I think you can get a sense of what I think about cancel culture. But otherwise, no. 

It’s not like I feel like I need to hide something — if you listen to my podcast, you get all of that stuff. So, there are fans who have different levels: “Oh, I want to know him.” I have people come up after the show and they’re like, “Can I meet Anthony?” And my tour manager will say, “Oh, sorry, he doesn’t meet people,” and they’re like, “Oh, yeah, I know, he hates people,” and they’ll walk off. I’ve kind of gotten that reputation with my fans that, if they’re a good fan, they want to leave me alone — they’ll come by and say, “Hey, that was really funny, I don’t want to bother you,” gone. If you want my personal life, you can find that through the podcast. But I think personal stories on stage in stand-up are boring. Unless you have some amazing story, I don’t want to hear it, and I think a lot of it becomes the same, and my stories would be the same. I’m not special — I would rather have something more creative on stage.

You’re never tempted to get more personal as you get older and experience more of life?

Oh, I’m tempted because it’s so much easier. I try it, and then I get sick of the story. I’m just like, “You know what? It is easier, I’m eating up 10 minutes, but why?” I didn’t only not tell stories in the beginning because I didn’t have much to talk about — it was because I was bored telling that same story. 

I told a story in Ryan Sickler’s podcast about bringing a knife to school when I was in the eighth grade — sell(ing) the knife and getting in trouble for it — and people love that story. I told it one night on stage and it killed, people were going nuts. I’m like, “Oh, okay, now I’ve got this 10-, 15-minute thing I can do to really get something off my chest,” and by the third time I told it, I was like, “I’m never telling this again, that’s over.” I just get bored, where like the abortion story from Fire in the Maternity Ward, it’s based on something that happened, but every single detail is a joke. I would much prefer to work in that format.

You’ve just toured this Bones and All material for two years. Why do those jokes never get boring for you?

I got to think it’s because (they’re) short. The jokes are very short, and the payoff, it’s not just the payoff for the audience, it’s the payoff for me. I like those laughs — I like those bursts of energy. If I’m telling a story, it’s not like I’m bombing, but it’s just there’s five minutes without a laugh — I start to feel anxious, and I don’t like feeling anxious. I don’t want that — I want to have those hits. Which is why the stories that I do have are just joke, joke, joke, joke, joke, because I don’t want to have that explanation period. And even if the audience is locked in (on a long story) — “We love this, and we are just focused on you” — I’m not comfortable. I would rather have the laughs. Maybe at some point, I come up with a story that I enjoy enough that will be like that, but I’ve tried it. I understand why people want it from me, and I also understand why it’s better that I don’t do it. There’s plenty of people who do.

Tony Hinchcliffe got a lot of blowback for his Madison Square Garden appearance at the Trump rally — specifically, for his offensive bit about Puerto Rico. Do you watch that and think, “I know how to make that joke work”?

I never would’ve put myself in that position, firstly — on either side. A political rally at Madison Square Garden, it was just the wrong joke to tell. I don’t have a problem with the joke — and listen, I love Puerto Rico, I’ve given money to Puerto Rico for earthquakes and hurricanes. I didn’t find it distasteful — it was like, “I get what you’re doing, but they’re constituents. You are trying to get them to vote for you, so what the fuck are you doing?” That was my big takeaway: You’re roasting the wrong things. 

If I had been hired by Donald Trump to do that, I would’ve roasted his opponents. I would’ve roasted states he was definitely going to lose that we could all laugh at. I think he just misjudged his audience, and that was the greatest sin. I think the joke is fine — I don’t think it’s a good joke, but I’m not as upset about it as some people were, unless you put it in the context of the opening of a last-minute political rally that, of course, didn’t change anything.

If your audience is more conservative, do you ever worry that they’re enjoying your jokes but not in the way that you intend?  

Sometimes it doesn’t really matter to me. I have one joke where I say I’m against cancel culture, and the audience cheers — I think they’re playing along. I think they know that I’m making fun of people who say that — they’re going to cheer because that’s what a hack comedy audience would cheer for. Sometimes I think they’re cheering because they know what’s about to happen — I rarely think they’re cheering because, “Yes, he’s on our side,” because they know I’m going to pull out the rug from them. If they’re coming to buy a ticket, they’re like, “I’m happy to have the rug pulled out from underneath me.” My audience is smart enough to not have to agree with everything I say and still enjoy themselves.

You appeared on Theo Von’s podcast, and you talked about successful comedy being about getting away with something. The clip went viral — how did you feel about that becoming such a big thing?

I was fine with it. I don’t love doing podcasts in general — Theo asked me to do it while I was in Cleveland, on a day off, and I was like, “Why am I doing this?” That clip, it was like, “Okay, this is good. If this went on my tombstone, I’d be happy.” 

But what I’m talking about more in that instance, I don’t think it’s bad to have jokes where the audience doesn’t laugh — you just can’t fucking complain about it. I have plenty of jokes where the audience doesn’t laugh and I have a backup joke to make them laugh at that, and then keep the show going. People who (tell) a joke that’s just a bad joke and then complain that you can’t say anything anymore, that to me is embarrassing as a comedian. Other comedians, it’s become the go-to space — “Cancel culture’s bad, we’re above it, come to this special comedy club we’ve invented where everyone laughs at our shit” — and that is weak. People are like, “Come play in the sandbox with us, we have our own little sandbox” — I want to play on the beach. 

If comedy’s not dangerous, if there aren’t consequences… a lot of these people want to take the consequences out. They want to be edgy, but they don’t want to get yelled at for it — and it’s just getting yelled at. People might lose a job here or there — in show business, people lose their jobs for different reasons all the time. Shows get canceled, actors get replaced, writers get replaced, and you can see that as being “cancel culture” — I think that’s just you chose a career in show business, and now what are you going to do with it? Are you going to be up here complaining about it the whole time? Because that to me is embarrassing, and I get mad as a fellow artist.

Have you lost any showbiz jobs because of your material?

I was always surprised that I was able to get on TV at all with five minutes of the jokes that I tell. I was doing my act to try to audition to have someone hire me to write for them — I never thought I would be a stand-up of this magnitude just because I thought, “They’re not going to let me on TV with this.” And this is before Netflix — it was like, “Could you get on Conan? Could you get on Premium Blend?” And I wasn’t sure in the beginning. 

I bought a watch (recently), and someone was like, “Oh, would you think about being a brand ambassador?” And I’m like, “No one’s going to make me a brand ambassador for anything. Half of my jokes are about killing children.” I’ve always been this person. I’ve never been in a commercial, I’ve never been in a movie, I’ve never really done any acting. I just like to do this.

I was gonna say: I was struck by how few acting credits you have on your IMDb page.

I would enjoy it because I enjoy the camaraderie. Stand-up is all on your own — (with acting), you’re working with people, I like that, I’m just not asked to do it very often. And, frankly, I’m surprised I'm not asked — I’m a good-looking guy, I have a very distinctive voice that I think (they) would use me in voice stuff. I think at some point people will start asking me. 

But I’m spoiled as a comic. I see comics who are making huge movies — huge movies — and I talk to them afterwards and they’re like, “I lost money. If I had just toured the whole time I was doing this movie, I would’ve done so much better.” It’s not something that I feel like I’m missing out on. And I’m not that good — the interesting characters, I wouldn’t be able to play. I would be thinking, “Oh, someone else should be doing this,” and that’s a bad thing for an actor to be thinking.

In this new special, I noticed that your hair is very different from your past special. The older, spikier haircut seemed more in keeping with a villain. Now, it’s a little softer, not as threatening. I assume you think about how the character looks on stage, so what prompted the change?

It’s something I don’t think about onstage, but it was something that I became very aware of after the last special, when there was a huge debate about beard versus non-beard. And (not just) as (what’s) better-looking — which is better for the character? The character seems more like a psychopath clean-shaven, but I’m like, “No, I like the beard.” (I decided) to grow my hair a little bit longer on tour — I just thought, “What would this do? Does this make me more of an asshole or less of an asshole?” And to be honest, I think that having more of a styled haircut seems a little bit scarier. It’s more of like “We’re putting on a show,” whereas the spiky haircut was easy to do. Anyone could do that — it seemed like I’m just walking out here doing this. 

This (new version) seems more like a performance to me. I’m curious to see what the reaction is to having a different-shaped beard and a different haircut — it was very much “Let’s see if this is scarier or less scary.” I feel like I’ve gotten more famous in the past couple years because of clips, and all the clips are short hair. The beard was something I can have a little bit of anonymity for a little while — growing my hair longer was like, “Okay, I feel like I have a little bit of anonymity in public,” and that’s helpful.

Steven WrightRodney Dangerfield and Mitch Hedberg are often cited as major influences. When did you first discover those guys?

It must have been late-night TV as a kid, waiting for those last five minutes of Carson to see who would show up — they would usually have a comic at the end. I’m sure I saw Steven Wright’s HBO special at some point, but I must’ve been introduced through late-night sets. Hedberg, I didn’t find out about until I’d been doing comedy for about a year. But Steven Wright was the first — and then Dangerfield was like, “Oh, okay, I’m into this guy, too” — but Steven Wright to me was huge. 

It’s impossible to listen to Wright’s material and not start mimicking his speaking style. Did you when you were starting out?

No, surprisingly not. You could say Christopher Walken, for sure, has had an impact on how I speak, even though my dad gets the same comparison. But Steven Wright was almost too much of a departure from my character. Maybe there would’ve been a couple years in college when I was smoking too much pot that I could have had a Hedberg kind of personality, but I never really had that burnout thing, either. It was more of just “How did they think of that crazy twist?” — it never really entered into my persona with my friends in the beginning.

Does your character evolve? Has he changed over time?

I think of the character as an aging punk rocker at this point in my existence. In the beginning it was, “There are no lines, fuck everybody, offend everyone, let’s fucking go,” and I’m glad I did that in my 20s, and that helped me out a lot. My idols who have softened as they get older, I find that to be interesting, and as the world changes, you find yourself going from the villain to the hero. 

I think a lot about my friend Steve Albini, who passed away this year, and his come-up through the punk scene and then coming out on the other side — not anti-punk, but he really hated a lot of stand-up comedy. One of the reasons we were friends is what he thought stand-up comedy had become. He was always on the side of the downtrodden, and he was never on the side of the winning team. Now, it seems like the jocks have taken over the school, and that drove him so crazy.  

My past is my past, and I’ll never apologize for it or try to whitewash it. But I think I’ve gained a lot of wisdom, a lot of knowledge and life experience — I like that I have softened, and that the act isn’t as hardcore as it used to be. I think that’s good, and I think that’s more interesting.

I don’t think of the character evolving, but as I write, I’m reacting to what’s popular around me. If the biggest comics in the world started getting real family-friendly, maybe I would go darker and would go harder, but there’s plenty of comics now that are just as dark and hardcore as I used to be. I think they lack my writing talent. Now, I just see a lot of cult of personality. I think having a popular podcast is more important than having a good act, and I think the second comedy boom, that has been unkillable, that’s how it dies, with the podcasting.

Podcasting has gotten really, really big in terms of selling tickets — you don’t really need to do anything else other than have a popular podcast to sell tickets. And you’ll have a great show because the audience loves it, and you’re never really testing anything out. That’s why you see all these podcasts put out a special. (They’re) immediately savaged by critics and forgotten about — to the point that people don’t want to write about it, because there’s no point in writing a negative review of something that’s just friends hanging out, which is what comedy is becoming.

With younger comics, they really need to pump out so much material to get noticed — and then chop it up into clips on social media.

I understand why the clips are popular and why they help. YouTube used to be the thing, now it really is TikTok and Instagram. Everyone says, “I love your clips,” and I think I’m uniquely suited to that (format), just through sheer luck, where you can use all my back catalog. Even though I haven’t been doing anything but touring for the past two years, I’ve had a social media team that’s gotten me close to a million followers on these platforms through just old things. 

I don’t know what I would be doing (if I was starting out today). I don’t know if I would have tried to get into more of multimedia, maybe tried to write more. Maybe I would’ve started my own podcast earlier on. I just always wanted to be a stand-up, and now it seems like the top thing you can do in stand-up comedy is not stand-up comedy — it’s podcasting. 

Podcasting is its own TV show now, and it’s gotten a little weird from my taste. It used to be “We’re just hanging out, fucking around, who’s listening to this? We’ve no idea.” And now it’s about money. Now it’s like, if I show up and I’m not in a good mood on your podcast, I’m costing you money. If I say something bad about your podcast, it’s affecting someone’s bag. I think that’s changed the art. I think talking trash about other comedians — comics being like, “That joke sucks, watch what I can do” — it’s like in hip-hop when everyone’s feuding all the time, it’s good for the art form. Whereas in stand-up now, where there’s so much money in podcasting, you just can’t say anything — otherwise you’re a hater, or you’re jealous of someone’s Patreon, which is insane to me that’s even a real thing. 

If you had told me that (I) would become a stand-up comedian, it would be my greatest dream. I don’t have a boss — I don’t have to listen to anyone. But if they’re like, “You better pay attention to what Joe Rogan thinks and what he says, because Joe Rogan can really help your career,” I’d be like, “What are you talking about?” And Joe’s fine, but I don’t want to live my life in a way that I have to worry about what he thinks. I’m sure as fuck not going to move to the city he lives in. I’m embarrassed by what a lot of comedy has become.

After the election, you made a joke on The Jeselnik & Rosenthal Vanity Project about becoming the “liberal Joe Rogan,” making fun of pundits wondering about the possibility of such a person emerging. Do you think a “liberal Joe Rogan” could happen?

I don’t think so. Conservatives have what works for them and a lot of that is conspiracy theory and “We’re ultra-masculine.” Joe Rogan doesn’t work without MMA. It used to be, like, he was the weed guy — now, he’s the weed guy and the MMA guy, and he’s perfectly suited to this role of the conservative Joe Rogan. 

A liberal Joe Rogan is just a pussy. I have people come to my shows and they say, as a progressive, “I hate progressive comedy because it’s so lame, and that when I’m watching your show, I know you’re progressive, and I know I'm in good hands, that I can laugh and enjoy it.” I don't know what a liberal Joe Rogan would look like, but it sounds like shit. It sounds like a children’s drawing of God — it has no bearing on reality. 

After Trump won, I thought, “So many of my friends and I are sad, but Jeselnik’s character wouldn’t be. He doesn’t get sad about anything.” I cannot imagine such a thing occurring, but was there any part of you that thought after the election, “I need to drop the mask. I need to talk sincerely about the problems affecting our world”? That just so doesn’t sound like you. 

Not only that, but it made me mad when anyone else would do it. Immediately after he got elected the first time, I was like, “Trump is president, we get it, we don’t want to hear about it.” My last special, I had that whole bit where you think I’m about to talk about politics — and it’s about dropping babies, because then that was my reaction to the embarrassment I felt coming off of comedians who felt like “My voice matters, I have to say this.” 

The one time I did feel like I had to get involved was when I started to see my name on lists of “top conservative comedians” and that people confused being against political correctness with being against correctness — I had to shut that down. I really don’t want to hate my fans, and there are plenty of very popular artists and comedians who despise their fan base, but I thought, “If I can just nip this in the bud…” I don’t have to be insulting — I have anti-gun jokes that aren’t insulting. I understand who my audience is. I’m going to speak my mind, but I’m not going to make it part of my art, not because I’m worried I’m going to upset you. I ended my last special with the 15-minute abortion story — that’s going to upset somebody — but if you’re like, “You must love Trump,” then I have to correct the record.

Throughout your career, you’ve often talked about being a great writer. You’re not modest about it. What makes you better than your peers?

I would say, as politically as I can, that I have a higher bar. I write more jokes and I fail with more jokes in order to get to that great one, where some people just say, “That’s good enough.” Some people are like, “I’m just going to go up there and talk,” and they get a laugh and that’s okay. I think some comics, they say something backstage and their friends laugh, and they’re like, “Oh, great,” and they go out and they say it on stage and the audience doesn’t laugh, and they’re like, “Huh, it’s still a good joke” — that’s not the way it works. 

I don’t think I’m more talented — I don’t think I’m smarter — I just think I have a little bit of a higher bar. That’s why it takes longer in between specials — I choose fewer projects because I really want to make every little bit of it great. But I think some people are like, “You know what? Let’s just make that wall look good and we’ll ignore the rest of the room.”

Earlier, you mentioned comics having to watch themselves in terms of talking shit about other comics because of this new “Don’t piss off anyone in the industry” mindset. Have you caught yourself holding your tongue for that very reason? 

There’s a subculture on YouTube where they collect clips and then put them together, and they’re making just as much money as everybody else. There was one where I was making fun of Bert Kreischer and Tom Segura for a lot of the stuff they were doing, but it was very subtle — in every episode (of my podcast) I would do a little thing. Then I run into Bert Kreischer at the Comedy Store, and he’s acting a little weird — he’s just not as gregarious as normal. And I get home and I see they put together all of these clips into one thing, and when you put it in without context, it looks like I’m trying to bury the guy — and it’s like, “No, I’m just fucking around.” 

I think I’m just too well-versed in what’s going on in comedy. I shouldn’t know anything about what Tim Dillon did last month, and I know so, so much. If I didn’t, would I be angry? Would I ever think about it again? Part of it is, I need that — the trans bit doesn’t exist without being very familiar with the road Chappelle’s been going down these last few years. I need to be a little bit involved in comedy to be upset about it, but I sometimes think it gets me a little bit too upset.

I was just thinking about your trans bit in Bones and All — it’s such a clear commentary on Dave Chappelle without ever saying so.

It’s more powerful to not use his name, but I can’t imagine you watch that bit without thinking that’s exactly who I’m talking about — and talking to. He’s considered the greatest stand-up comic alive right now, and he’s been riding this wave of bullshit for so, so long that I think it would’ve done the bit a disservice to actually say his name. But I don’t know how you could watch that without understanding it.

I hope that, in the same way that I think that Thoughts and Prayer stopped people from saying, “thoughts and prayers,” I would hope that (my trans bit) squashes 99 percent of trans material. I think, obviously, make fun of these people, but you can make jokes about race without the racial slurs — that’s something that I will never condone in comedy. I’m hoping that maybe people will up their game a little bit, especially in terms of trans material. It doesn’t have to be this lightning rod — it can just be a subject.

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