Michelle Wolf is preparing for her second stand-up special, her own Netflix show and the White House Correspondents’ Association dinner, where she’ll roast Washington’s elite.
“[Trump’s] terrible for comedy. He does crazy stuff all the time, but you can only make so many jokes about it before they all sound the same,” Wolf said of President Trump. “It’s gotten comedy into a place where it’s turned more into activism, and that’s not where comedy is good.”
She added, “Comedy, in my opinion, is best when it’s in the gray and you’re kind of pushing people’s thoughts that they sort of had but never vocalized. And I think a joke is not good if someone says something and immediately people are clapping because they’re like, ‘Yes! That is how I feel as well!’”
The 32-year-old Hershey, Pa., native had been working in finance and contemplating a kinesiology PhD when she first tried comedy in 2008. Ten years later, she’s headlining one of comedy’s toughest gigs, and her new weekly series, “The Break with Michelle Wolf,” premieres May 27 on Netflix. She wants to not just talk about politics, but get into sports, science and entertainment, too, with a more stand-up approach than one-off, monologue-style jokes with just a setup and punchline, plus sketches and guests.
Her ascent may seem remarkable, but Wolf’s former boss Seth Meyers said her career is just the product of pure grit and talent.
“She takes comedy very seriously as a job, and she puts an incredible hours. She was the kind of person who would do her work here, and then she would still be here when the show was over because she had to kill time before she went out to do, you know, somewhere between six and a hundred sets that night,” the NBC host said. “I don’t think she caught breaks as much as she fought her way in the door . . . She made her own luck. She created as many opportunities as possible for people to see her and be impressed by her.”
Wolf joined “Late Night with Seth Meyers” as a writer in 2014, a year to the date after quitting her job and doing comedy full-time. In 2016, she became an on-air contributor to “The Daily Show with Trevor Noah.” She wrote Oscars jokes for Chris Rock and opened for him on his comeback tour. In 2017, she released her debut stand-up special, HBO’s “Nice Lady,” praised by critics as one of the year’s best.
Her comedy also feels urgently needed, at a time when society is grappling with sexual misconduct allegations and gender inequality. In “Nice Lady,” she jokes about the rejection of ambitious women and Hillary Clinton (“We’re never going to have a nice lady run for president. Nice ladies aren’t in charge of things.”); feminism (“I’m not, like, a buy-my-own-drinks kind of feminist. It’s like, I want equal pay — and a chardonnay.”); and her own “shrill” voice (“You don’t get to choose your voice! I was never like, ‘Oh, I’ll take the voice that causes dogs to gather outside.’”).
Like last year, Trump plans to skip the dinner. Wolf will definitely tell jokes about him, but there are plenty of people that will get roasted.
There’s so much to address: the frenzied news cycle, media personalities, youth gun-violence activists and the “Me Too” movement.
“She is fearless,” Meyers told The Post. “The problem with that gig is the ability to also not care how they’re going at any given point, and she is perfectly designed for that.”
A year ago, Harvey Weinstein mansplained comedy to Wolf after seeing her perform at a charity event. Wolf had told just one Trump joke “because even then, I had total Trump fatigue.” Later, Wolf and Weinstein ended up in the same elevator after.
“You should have talked about Trump the whole time,” Wolf remembered Weinstein telling her. “I didn’t want to,” she replied. “You should have,” he continued.
“I don’t think so,” Wolf said, and then she got off the elevator (“unscathed,” she adds).