Michelle Wolf Trusts That the Joke’s Not on Her

Before she became a comedian, Michelle Wolf was a high school track star whose experience as a high jumper taught her a lasting metaphor about life.

A high jumper, Wolf recently explained, must leap over a bar raised to increasingly greater heights until she inevitably fails to clear it.

“You could have the best jump of your career, and then you still end on a failure,” she said. “It’s like, ‘Yeah, that was your best — but you could do better.'”

That nagging insecurity has gone hand in hand with the rapid accomplishments of Wolf, a 32-year-old stand-up who has contributed to “Late Night With Seth Meyers” and “The Daily Show With Trevor Noah.”

Among her latest career high points: On Saturday, she will be the featured entertainer at the White House Correspondents’ Association dinner, the annual, increasingly fraught Washington gathering of news media figures, politicians and celebrities.

Then on May 27, her new topical comedy series, “The Break With Michelle Wolf,” will make its debut on Netflix.

These are opportunities that Wolf sees as sources of both prestige and anxiety — the fruits of her hard work and obligations to make herself work even harder, while she waits for the bottom to drop out.

“I think I’m a good joke writer,” she said. “I’m also very scared that the last joke I wrote is the last joke I’ll ever write.”

On a Friday afternoon earlier this month, Wolf was in her office at the Manhattan studio where “The Break” is being produced. Stretched out on a velvet couch, she was explaining the sensibility that she is shooting for at the dinner and in her Netflix show.

Wolf is no fan of President Donald Trump’s, and was relieved when it was announced that for the second year, he would not be attending the dinner.

“I thought, oh, thank God, I don’t have to hear him eat,” she said.

Still, she said there was limited value in standing in front of a crowd and cracking a bunch of knee-jerk jokes about Trump.

“The audience cheers, but that isn’t comedy,” she said. “It’s just a rally.”

Wolf said she was not interested in what she called “cool-teacher comedy — we’re going to learn and have fun at the same time.”

“You don’t want to say what people want you to say,” she added. “You want to say what people didn’t know they wanted you to say.” Wolf, who grew up in Hershey, Pennsylvania, has been following her own muse since she quit her career in finance (where she’d worked at banks like Bear Stearns and JPMorgan Chase) to take improv classes at Upright Citizens Brigade Theater and the Pit in New York.

“Eventually people in improv were like, ‘You’re more of a stand-up,'” Wolf said. “I think they were gently trying to tell me I was selfish.”

In performance, Wolf can be her own harshest critic, then suddenly turn that scathing sensibility on her audience and its unexplored assumptions.

In a riff from her 2017 HBO special, “Nice Lady,” she takes aim at her least favorite qualities about herself — a speaking voice she says is shrill; her lackluster commitment to feminism — and mocks Hillary Clinton for losing the 2016 election “because no one likes her.”

But Wolf also laments the expectation that women must surrender their likability to attain power. “If you’re in charge of things and you think you’re a nice lady, no one else does,” she says in the set. “There are whole email chains about how much you’re not a nice lady.”

Her stand-up shows attracted the attention of producers at “Late Night,” where Meyers hired her when he became its host in 2014.

“She’s self-deprecating, yes, but very good at deprecating others,” Meyers said. “She’s either the meanest nice person I know or the nicest mean person I know.”

Though she was hired primarily to write comedy sketches and jokes for Meyers’ monologue, Wolf often appeared on camera, performing her own stand-up and playing characters like a grown-up version of Little Orphan Annie.

When “The Daily Show” hired her away in 2016, Meyers said he did not begrudge her departure.

“Her whip-crack of a cackle was a fun thing to hear when my jokes were bombing,” he said. “I wish she’d take more pleasure in my successes, but she really seems to enjoy when I fail.”

At “The Daily Show,” Wolf delivered riffs about Harvey Weinstein and the #MeToo movement, the implications of Clinton’s loss to Trump and the cultural impact of the “Wonder Woman” movie.

She also worked relentlessly on her stand-up outside the show, performing as many as 15 or 20 sets a week, by her estimate, at clubs like the Comedy Cellar and Village Underground. Neal Brennan, the “Chappelle’s Show” co-creator who directed Wolf in “Nice Lady,” invoked her history as an athlete to describe her work ethic.

“She is competitive, without being competitive against specific people,” Brennan said. “She is competitive against the track and the time. And she really pushes herself. I know some very hard-working people, and you’re not going to outwork her.”

The White House Correspondents’ Association dinner has previously been hosted by late-night stars like Meyers, Stephen Colbert and Jimmy Kimmel, but its emcees can expect to come under intense scrutiny and have their monologues picked apart on a joke-by-joke basis.

When Wolf was approached about the gig, she said she was ambivalent.

“It’s a weird time, if you’ve noticed,” she said with a laugh. That same day she sat herself down and wrote “a ton of jokes,” just to prove to herself that she could do it. The Correspondents’ Association dinner, she said, is “really a homework assignment.”

Having to prepare her set at the same time she is readying her Netflix show was “not the dream timeline,” Wolf said, but the side-by-side assignments were helping her to focus.

Wolf is just one of many “Daily Show” alums who are stepping out with new comedy programs. In addition to the many late-night shows already on broadcast and cable TV, HBO recently introduced “Wyatt Cenac’s Problem Areas,” and Netflix is preparing a weekly talk show starring Hasan Minhaj for later this year.

Still, Wolf’s peers and admirers feel that her voice is distinctive enough to break through.

Seth Rogen, who cast Wolf in his “Hilarity for Charity” comedy special on Netflix, said she was a rare stand-up who could tackle timely subjects without sounding tedious or didactic.

Watching Wolf perform, he said: “It doesn’t feel like you’re eating your vegetables. It never feels like you’re patiently sitting through her ideology to get to the joke.” Having seen and appeared on every late-night show of the modern era, Rogen said, “I’m much more inclined to watch things that are not traditional talk shows, rather than a person on a super-glitzy stage in some theater that’s been used for the last 250 years.”

At her Manhattan office — whose previous occupants have included Jon Stewart, Colbert and Larry Wilmore — Wolf was getting ready to tape her first episodes of “The Break,” which she said would mix stand-up monologues with comedy sketches.

She was also trying to figure out how to strike the right balance between breaking the mold of late-night TV and carrying on its familiar traditions.

A few days earlier, she had taken her first look at the set she will use on “The Break.” Initially, Wolf had told her set designer that she did not want it to have the familiar element of a city skyline in the background. Nonetheless, the designer showed her two options: one with a skyline, and one without.