Upon taking the stage, comedian Anthony Jeselnik seems serene, composed and unaffected. His delivery is precise and deliberate. Basically, he’s a standup surgeon deftly slicing up an audience until its laughs and gasps are intermixed.

Originally from Pittsburgh, PA, Jeselnik is the first-born in a family of five kids. His comic career began in school, he says, where dark, inappropriate humor was his classroom specialty. However, it took a few years onstage to help him rediscover himself. At first he plied his trade doing old-school, “let me tell a funny story” – style comedy, but it clearly wasn’t his bag. His niche was the darker side of laughter – jokes with a sociopathic edge.

If there’s a line to cross, Jeselnik will cross it. Naturally, Comedy Central’s roasts were a perfect fit for him: His comic unkindness to Charlie Sheen and Donald Trump catapulted him to stardom, and he’s since moved on to his own TV show, The Jeselnik Offensive, which just concluded its second season.

In person, he’s thoughtful and engaging, eager to dissect the art of making people laugh. Comedy is a deadly serious business for Jeselnik, who has become a veritable master of the “gut punch,” the kind of joke that both surprises and rattles you – and makes you laugh hard in spite of your so-called “sensitivities.” But in order to succeed using that weapon, a comedian must be part psychologist, part sadist and part court jester. Jeselnik’s toolkit is full.

When we interviewed Roseanne (July ’13), we asked her whether she thought comedy has grown more mean-spirited – and we cited your comedy as example.
I think comedy just goes in waves. Comedy got really silly and observational for a long time; people coming up wanted to do something different. I know I went mean-spirited because it got a bigger laugh. It’s a harsher kind of gut punch that I really enjoy.

Woody Allen has said that comedy has its roots in hostility. What do you think?
Sure, and I think a lot of people hide that. I don’t know what people need from an audience, but I think a different class of comedians is coming up now who are ...

I don’t want to say “smarter,” but they could have done something else. I could have been a lawyer if I’d wanted to go that route. But I got into comedy.

Your comedy can be hilarious to some, highly offensive to others.
I started when I was 23 years old, and I didn’t have a damn thing to say to anybody. Who would ever want to listen to one of my stories or get something out of it? I hadn’t lived that interesting of a life. I thought that if I could just write jokes, take my act outside of myself, the world would be my oyster. And everything opened up: I could talk about whatever I wanted. I was more interested in subject matter and why things made people uncomfortable and why it was okay to make a joke about a tragedy a couple weeks later but not the day of. Could I find the perfect joke and make people laugh the day of a tragedy?

On your show, you made a joke about the Newtown school shooting. The reaction of the audience was decidedly negative.
Not every joke has to be this big winner. Sometimes you gotta throw a fastball inside just to keep people on their toes. It’s fun to approach a subject like that with complete disregard.

Twenty years ago, Andrew Dice Clay was savaged for his act. Some Saturday Night Live cast members even refused to go on if he hosted.
It was mostly Jan Hooks. It was going to be her last season anyway – she was just trying to get publicity. When you look back, it wasn’t that big of deal. But it was crazy that she would not see him as an artist. It’s like saying: “I’m not going to share the stage with Stephen King because he’s killed so many people in his books.”

Do you think you might have suffered the same treatment back then?
Sure, it’s possible. But I think that every time that kind of thing happens, everybody takes a step back. Daniel Tosh got in trouble with the rape-joke controversy, but I have three of them in my special. It’s not a big deal, because everyone kind of went crazy over him. It’s like yelling “Wolf !” – the next time, people just aren’t that interested.

What makes you laugh?
The unexpected ... and it’s got to be a smarter joke. People think I must love dark humor. Not particularly – I do dark humor, but I like the more absurd people. I hate easy comedy. If I get the punch line before you do, it’s not good.

What’s contributed more to your comedy, school or family?
I’d have to say school. I never got a good explanation for why I had to take calculus: If I don’t care about this, but I’m passionate about that, why can’t I just go do that?

I was in a public school that really didn’t have a creative outlet for me. I’d make jokes in class, and they were always kind of darker and more inappropriate. That freaked people out, so they kind of made me feel I was wrong for a long portion of my life.

So how did you find your voice as a comedian?
I think a lot of comedians kind of just take their influences. I like Mitch Hedberg and I like Steven Wright. I started telling stories, and one day I saw a comedian – B.J. Novak, who’s now a rich, famous person – doing one-liners, smart jokes. Some hit and some didn’t, and I was like, “Wow! I can do that!” Steven Wright’s a genius, but I thought, “I can’t do that – I have to do something else.”

So I thought, “What’s the funniest thing in the world to me?” And it was “Deep Thoughts by Jack Handy” [from Saturday Night Live]. I loved those so much, but I found that deep thoughts, if said out loud, didn’t always get a big laugh.

But I kept playing with the structure. And one day I told a mean version of a Jack Handy joke – and just the sound the crowd made, it was like a light-bulb moment. Everything fit, made sense to me. I started chasing that, and as I started chasing those jokes, my persona had to fit: I couldn’t really be a nice guy.

There always seems to be a small glimmer that says you’re just joking – maybe a slight smile.
Absolutely, and I don’t try to hide that. But it’s got to be natural. I don’t smile just to let the audience know I’m laughing that they’re laughing at this shit. I don’t feel the need to be like: “I’m just joking. We’re all just having fun.” I hate when comedians do that – I just hate it.

You have to cope with failure as a comic: You’re either funny or you’re not.
If you’re not failing, you’re not getting better. If I have a great set, and I kill with a standing ovation, I walk offstage thinking, “I know comedy!” But when I have a bad set, I think, “How can I fix this? What can I do to get better so that it never happens again?”

If I’m doing crowd work like, “Hey, what do you do for a living?”, and they say, “I’m an obstetrician,” and I don’t have a joke ready, that haunts me. The next time I’m in that situation – even though maybe it never happens again – I’m ready for it. Success doesn’t teach you anything.

Have you ever regretted any of the jokes you’ve told?
No.

Not a one?
No, not one. If the joke fails, it doesn’t matter; people are still being entertained. I’m still doing a good job, but I’m trying different things that might not work. But I’ve never been like, “Ah, that went too far.”

Back to the Newtown joke: You were on really delicate ground, and the audience didn’t buy into it at all. That’s not a problem for you?
Not at all. Why does everything have to hit? Again, it’s a fastball inside. Why not keep them kind of off-guard? That way, they don’t know what’s coming next. A joke can fail, but it can still set up the next joke. I don’t worry about that at all.

So you’re not concerned with displaying sensitivity toward current tragic events – about crossing that invisible line?
Everyone’s got their own line, and I don’t care about any of them. I’m trying to go over that line and still make the joke work. I’m not doing it just to be a jerk; it’s mostly wordplay, and I know little tricks of the trade, how to make someone laugh. Like the day of the Aurora shooting, I tweeted a joke: “Other than that, how was the movie?” [HT laughs.] Exactly. It didn’t make you think of the victims or anything – it just made you laugh on that horrible day. But that was like a perfect version. I thought that I had nailed it.

But when the Boston Marathon bombing happened, I tweeted: “Guys, today there are just some lines that should not be crossed – especially the finish line.” And people went crazy.

Crazy good or bad?
Bad. During Aurora, I was just a comedian. Now that I’m kind of a celebrity, people saw my name and the joke during the Boston Marathon. The joke isn’t really offensive to anyone who was there, but it makes light of the situation, and that really turned people off. At Comedy Central, my bosses made me delete the tweet, which I didn’t think was right. I felt it would have gone away and people would forget about it. The joke itself isn’t about the victims; it’s just about the event.

People say, “My thoughts and prayers are with you.” I’m a comedian – you don’t need my thoughts and prayers. Let me try to make a joke, and if it doesn’t work, I don’t need applause. I also don’t think I should be punished for that. It’s what I do. I don’t feel the need to be extra-careful. I’ve created this persona so that I can talk about these horrible things; sometimes it works and sometimes it doesn’t. But if I didn’t try, that would be a failure.

Timing is critical to what you do. Do you labor over the construction of your jokes?
It comes naturally to me. I couldn’t tell you the rules of grammar, but if I’m reading a book and the sentence is grammatically incorrect, I’m aware of it right away. I know what should be switched, but I can’t tell you why. It’s like that with the joke. I write it almost like a poem, like a deep thought that Jack Handy would write. The end of the line is where I might pause in the joke, to keep the audience just off-guard enough. When you slow the joke down enough, it invites them to try to guess the punch line. But then you take it away.

I was an English lit major. I think just by reading so much, the construction of a joke became second nature.

Does political humor interest you?
I don’t like political humor because you’re preaching to your audience always. I’m a staunch liberal, but if I made a joke about being a liberal, the liberals are going to laugh, the conservatives aren’t, and that’s all you’re going to get. I want everyone to laugh at human conditions, not just the political.

How is doing The Jeselnik Offensive different from standup?
The first show was a tough situation. You’re doing your best and you’re excited. I didn’t feel nervous, but I felt unsure – you’re trying to look as comfortable as you can, but it’s a losing game. I didn’t know how everything worked then. Now, by episode 10, it’s a much different person up there.

It’s also a completely different skill set than doing stand-up. If I’m doing standup and tell a joke, people laugh for 30 seconds – and I let them laugh for 30 seconds. But on the show, I’ve got to cut them off because I’ve got to keep it moving. That took a couple of episodes to get used to.

Do you ever write pot jokes?
I try to have a couple, but it’s tough to write a good marijuana joke. You can joke about it – the silly stuff, the “I’m a stoner and I smoke pot” kind of thing. But I wouldn’t consider myself a stoner in the way the culture does. A guy like Doug Benson can be goofy and talk about it and everyone loves it, but it really doesn’t jive with my persona. But if I thought of something great, I’d be thrilled to have it.

Are you a medical patient here in California?
I have a medical card ... for anxiety or something.

Do you suffer from anxiety?
Occasionally. Everyone does. But if I didn’t smoke, would I be okay? Of course.

I lived in New York for a few years, where they don’t have a medical marijuana program; you had to use a delivery service or something. When I came back to LA, I thought, “I’m a known person now. I’m famous as being a comedian. Who the hell is going to bust me for marijuana? I don’t need to get my medical marijuana card; I’ll just get it where I get it.” Then, within a week, a cop came up to me. I was smoking after a charity show I’d done – like backstage, it wasn’t even in public – and the cop asked if I had my medical marijuana card. I lied and said I didn’t have it on me. He gave me some crap, but let me go. I went out the next day and got my card, just to be safe. Why not?

Do you use marijuana at all to create?
I can’t use it to be creative – I’m creative without it. I just think it gives you a different angle. You build a sculpture and you think it looks pretty great, but then you smoke and you look at it from a different angle and you can see little things you can shave off or take in a different direction. Sometimes I’ve written jokes while high and think, “This is really funny.” But the next day, I find it’s just way too long and doesn’t make sense ... why did I think this was so good? It’s just a tool you can use, but to get the most out of it, you’ve got to use it effectively.

What misinformation about pot annoys you the most?
I hate that people call it a “gateway drug.” I’ve done a lot of different drugs in my life – and if it wasn’t for marijuana, I think I’d be doing heavier stuff. I enjoy drinking and I enjoy smoking. I think that smoking almost keeps me safe, you know what I mean? I drink less because of it. It helps me to medicate without doing too much damage to myself.

You know the quote “The answer to all your questions is money”? I think when people realize how much money can be made, what legalizing marijuana can do for the economy, but also turn away from the misinformation about it, then I think it will be generational breakthrough. People are getting smarter about it, and as the older generations pass on, I think marijuana will be everywhere in the next 20 years. I think it’s weird what’s going on – but I think we’re moving towards something better.

Visit anthonyjeselnik.com.

This article was featured in the December 2013 issue of HIGH TIMES magazine. Get a digital download of HIGH TIMES, or subscribe today!