Anthony Jeselnik: The Dark Prince Of Comedy

Published August 14, 2014 at 10:16 AM EDT

Comedian Anthony Jeselnik takes pride in joking about the topics you shouldn't joke about. Throughout his career, he's developed a snarky onstage persona delivering material about death and disease at comedy clubs, the roasts of Donald Trump and Charlie Sheen, and on his Comedy Central show, The Jeselnik Offensive.

Jeselnik joined Ask Me Another host Ophira Eisenberg to discuss his comic style. Before earning the moniker "the Dark Prince of Comedy," Jeselnik recalls trying to win over a crowd by mimicking his comedic idol, former Saturday Night Live writer Jack Handey. "As a comedian, you start, and you start trying things, and the audience tells you what your next step is going to be," Jeselnik said. "For me, the cockier I got, and the darker I got, and the meaner I got, the more the crowd followed that. So I thought, 'Okay, this is going to be a lot of fun.' "

When asked what topics he was interested in being quizzed on, Jeselnik mentioned sharks. So in an Ask Me Another Challenge called "Sharks With Snark," Jeselnik tackled questions about the underwater predators' appearances in popular culture, like the origin of the nickname Steven Spielberg gave the mechanical shark in Jaws.

Interview Highlights

How his on stage persona differs from his off-stage persona

People are very scared of me because they've seen the stage persona, and when they meet me, they're kind of taken off guard, and I like that. I want you to be scared so that I can be seem charming. People will be like, "Oh, you're so nice." I'm like, "I'm not that nice, you just think I'm gonna be really, really mean."

Why no topic is off limits

If something made me uncomfortable, I would take it as a challenge to try and make a joke about that. That's my only goal: to find things that you shouldn't joke about, and find a way to make a joke.

Why his performance on Comedy Central's Roast of Donald Trump changed his life

If I do badly on [the roast], then everything my life has been leading up to has been for nothing. Because this was my opportunity, and if it goes well, then I know I've been on the right path and things will continue to go well. So when I did well, people thought, "Oh, you're going to get so cocky when the roast is over," because I was cocky before. But after the roast, I kind of calmed down, because I didn't have to be cocky — everyone knew.

This segment originally appeared on April 14, 2014