Michelle Wolf didn’t plan to sleep within steps of the White House. She just likes old hotels.
Wolf also didn’t plan a life of comedy. Growing up, telling jokes never occurred to her as viable career path. Yet here she was, 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 — including the man who lives across the street.
“He’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.
Late-night shows are “kind of telling the news with jokes along the way, and there’s clearly a space for it because there’s like seven shows that do that,” she said. “But I want to go back to where it’s like comedy first, jokes first. I’m not trying to make a point. I’m just trying to make people laugh.”
She added: “You’re never going to learn about the TPP on my show.”
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 in 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.
“I’m sure to her, it doesn’t feel meteoric at all,” Meyers continued, “because she did it one step at a time, and particularly in New York doing these stand-up clubs where there’s so much competition. You kind of just have to grind it out.”
She also worked hard at the College of William & Mary, where she got good grades, competed in track and field and majored in kinesiology. Looking for a change after graduation, Wolf joined her fellow track teammates in New York City and worked in finance, getting a Bear Stearns job around the time of the financial collapse.
Then she went to a “Saturday Night Live” taping in 2008: “Always being such a big fan, I was like, ‘How did they do that? How do you get here?’ ”
A quick Google search revealed that most of the cast started in improv. Wolf promptly signed up for a class at the Peoples Improv Theater Comedy School. There, people would say, “‘I think you should try stand-up,’ ” she recalled. “Which I think is a nice way of saying, ‘You’re very selfish.’ ”
“I kept telling jokes onstage rather than reacting,” she said. And while improv disappears after the show, stand-up lets her build up a body of work over time.
So she threw herself into stand-up the way she did any other kind of training, and soon was performing nearly two dozen times a week. She tweeted constantly, which taught her economy of words and joke-writing.
“Very early on, I met this one comic who said if you’re not doing stand-up every night, you’re not doing it,” Wolf said. “And so I just kind of believed that and worked off that.”
Over the years, Wolf refined her comedic voice. In both her stand-up act and on “The Daily Show,” her jokes “might be sort of politically based, but I look at it from more of a social perspective,” and “from more of a macro level,” she said. For instance, a segment about an all-male Senate panel on health care became a bit about men being clueless about menstruation.
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.’ ”).
Wolf’s slightly chipper demeanor has a caustic edge to it. “It’s really fun to have someone who is mostly nice but also a little mean and enjoys her own meanness,” Meyers said. “But then she enjoys her meanness in a way that, because she’s so charismatic, convinces you to also enjoy the meanness.”
When performing stand-up, she’ll try to find the kind of person in the audience that she’s making fun of, so she can see their reaction. “I don’t want to alienate anybody,” she said. “If you’re making a joke about men and men are laughing at it, it’s a good joke.”
She operates on the “if you offend everyone, you offend no one” approach, which will apply to both her Netflix series and her WHCA dinner act. “We all deserve to get made fun of. I mean, I think we’re all idiots trying not to die, essentially,” she said. “Some of us are bigger idiots than others.”
Like last year, Trump plans to skip the dinner. Wolf will definitely tell jokes about him, but there are plenty of people who will get roasted.
There’s so much to address: the frenzied news cycle, media personalities, youth gun-violence activists, the #MeToo movement.
In fact, just 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.
“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).
When she was asked to perform at Saturday’s dinner, Wolf called up Meyers. Should she do it? He performed at the infamous 2011 dinner, where he made fun of Trump.
Wolf said he told her to make her jokes very specific and directly address particular people in the room. The room — a cavernous ballroom containing people with fragile egos and wearing uncomfortable clothes — is notoriously difficult for a comic.
Meyers encouraged her to take the gig.
“She is fearless,” he 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.”
Cowering from a challenge isn’t in Wolf’s disposition. For her, the bar always gets raised. She was a high-jumper, after all.
“The thing about high jump is that you can jump your very best, the best you’ve ever jumped, and they’re still going to raise the bar until you get out,” she said. “So you have days where you jump the best you’ve ever jumped, and they still raise the bar so you always end failing.”
“It’s kind of, I don’t know, sort of a philosophy for life?” she continued. “Like, yeah, you did great — but there’s another thing.”