Anthony Jeselnik and how to get away with being offensive

Nikki Glaser: “My favorite game to play when I watch his specials is, after the setup, to try to predict the punch line. I never can.”

In this Vulture profile, Anthony Jeselnik discusses how he gets away with joking about taboo topics.

The secret to saying a bunch of offensive stuff: Make the punchline legitimately surprising.

Something that helps with that: Being a narrator that’s “effortlessly cruel for no reason.”

The mistake other comics make: Leaning into the cruelty without offering genuine surprise.

The moment his comedic voice really clicked, he says, is when he wrote a joke he’s talked about repeatedly in interviews. “My girlfriend likes to joke she’s got a chocolate addiction,” the line goes. “So I put her in the car and I drove her downtown, and I pointed out a crack addict. And I said, ‘See that, honey? Why can’t you be that skinny?’” He taped it for the Comedy Central Presents special, and while the crowd hollers in shock when the punch line arrives, Jeselnik pulls what will become a characteristic expression throughout his career: a shit-eating grin. Jeselnik describes this as “a mean, smart joke you couldn’t see coming.” He was not making a conscious choice to try a specific personality onstage or carefully craft an identity; instead, it was his discovery that the unexpected punch lines he liked best required him to become a certain kind of narrator — to be, as he puts it, “effortlessly cruel for no reason.”

…

The end of the joke is designed to outrage an audience, and it does that job well. But the reveal of it, the twist, is not that the girlfriend in that joke is annoying or that cocaine addicts are idiots. It’s that the teller of the joke is a jerk, even more of a jerk than the setup initially suggests. Offensiveness is often so predictable, following along rote, well-worn pathways of racism, sexism, homophobia, and other fears. Jeselnik’s art is in finding ways to be such an astonishing asshole that the nature of the insult is legitimately surprising. His punch lines are cartographic: His material lives along the lurking boundaries of cultural taboos, and the act of crossing them makes those lines brightly visible. Comedian Nikki Glaser, who started in the L.A. comedy scene not long after Jeselnik, was drawn to his work because of its similarity to her own sensibility. “My favorite game to play when I watch his specials is, after the setup, to try to predict the punch line. I never can,” she says. “So many of us feel pressure to reinvent ourselves, or to get more honest, or reveal more about ourselves. He’s kept it … You know, you can’t pin down what he’s about.”

Photo: Ryan Pfluger

Up ahead: Why Jeselnik hates one-man shows and a bunch of Jeselinks on how he writes jokes, Norm Macdonald, and more.