Chasing the Last Laugh

Apr 23, 2019    12 min read

A year after her infamous White House Correspondents dinner, Michelle Wolf is ready to do it again

Written by
Stephen Rodrick
Photographed by
David Urbanke

Michelle Wolf is not a fan of Donald Trump humor. She thinks it’s all a bit hacky. “I personally hate Trump jokes,” says Wolf, who a year ago vowed to burn down the annual White House Correspondents’ Association Dinner and then did so in such definitive fashion nothing was left except scorched tuxedos. She doubles down: “I have not heard a good Trump joke in years.”

Alas, on a recent frozen night at New York’s legendary Comedy Cellar, three of the four comedians who take the stage before Wolf unleash Trump jokes. They are all lame. Then Wolf makes her way to the mike through a maze of tables occupied by drunk accountants and couples on first dates. She’s wearing blue jeans, a gray sweater and a muted pair of Nikes. (The long-distance runner has become known for performing in glam high-topped sneaks, her collection being her concession to consumerism.) Her trademark voluminous curly red hair—which Wolf once described on The Daily Show With Trevor Noah as a hybrid of classic Annie and modern African American Annie—has been straightened.

Wolf is working on new material, which means her routine is semi-embargoed. Suffice it to say, there are no Trump jokes. Her 2017 HBO special, Nice Lady, featured bits on period farts, the impossibility of the modern woman having it all and a theory that men’s testicles resemble a goblin’s coin purse. Her new material is in the same unfiltered vein.

At one point she seems to suggest—in a high-pitched voice she jokes often attracts stray dogs—that men don’t need to worry about the women’s movement because women have a tendency to devour their own. For anyone who paid attention to the aftermath of Wolf’s Correspondents’ Dinner set, it’s obvious why sharing this is not in breach of the embargo.

When Wolf finishes a few minutes later, she leaves the claustrophobic basement to applause exponentially louder than the combined clapping for all the dudes with the Trump jokes. It was her 10th show of the week.

Before April 28, 2018, you may have recognized Michelle Wolf only from bits she did on Late Night With Seth Meyers and The Daily Show. She’d written jokes for Chris Rock’s 2016 Academy Awards monologue and nabbed her HBO special a year later. But last year’s Correspondents’ Dinner propelled her into a different orbit, one filled with Fox News condemnations and finger-wagging from professional women who thought she’d been too harsh on White House press secretary Sarah Huckabee Sanders, a proven serial liar. Some even suggest the WHCA’s decision to have presidential biographer Ron Chernow deliver this year’s keynote was in response to Wolf’s polarizing set. It’s the first time a comedian hasn’t performed at the event since 2003.

There’s just one thing: Michelle Wolf does not give a fuck. She knew exactly what she was doing.

When Wolf was first approached to speak at the dinner—D.C.’s chummy get-together between plush talking heads and the plutocrats and politicians they’re supposedly holding accountable—she thought there must have been a mistake. “They were like, ‘We’ll get a woman,’ ” she tells me backstage at another of her shows, this time at Nashville’s Zanies. “I’m sure they thought, She won’t do anything crazy. She’ll be nice.” Wolf smiles. “They should have done more research on me.”

Before she took the stage, a comedian friend slipped her a note: “Burn it down.”

While Wolf is wary of her comedy epitaph becoming “The Girl From the Correspondents’ Dinner,” she’s happy to set the record straight and settle some scores. Before accepting the gig, Wolf talked with Meyers, her ex-boss and mentor, who had given the dinner keynote in 2011, and asked if she should do it. He told her yes but warned about performing in a room with bad acoustics and drunken robber barons barely paying attention.

“I made the decision to not cater to them,” Wolf tells me. “I don’t like what they’re doing right now. I don’t think it’s the right time for them to have a chuckle at the way things are going.”

Before she took the stage, a comedian friend slipped her a note: “Burn it down.” Another texted, “If they’re cringing, you’re doing it right.” Shortly before the ceremony started, she ran into Margaret Talev, a Bloomberg reporter and WHCA board member. That’s when she realized the organizers were in for a shock. Talev asked if Wolf would be wearing a gown. She told Talev she was going to wear a suit.

“Margaret said, ‘Oh, I’m wearing pants too. It’s like my little stick-it-to-the-man.’ I thought to myself, Oh, you have no idea what is coming,” Wolf says.

What has been forgotten in the swirl of post-dinner contretemps is that Wolf was an equal-opportunity slagger. She went after Al Franken, who had been forced to resign after allegations of groping: “Things are changing; men are being held accountable. Al Franken was ousted. That one really hurt liberals. I believe it was the great Ted Kennedy who said, ‘Wow, that’s crazy. I murdered a woman.’ ”

The room grumbled at the reference to a character who delights in oppressing other women. Wolf pressed on.

She threw a zinger at liberal saint Rachel Maddow, calling her “the Peter Pan of MSNBC, but instead of never growing up, she never gets to the point.” She went after MSNBC’s Morning Joe hosts: “I watch Morning Joe every morning. We now know Mika and Joe are engaged. Congratulations, you guys. It’s like when #MeToo works out.”

Wolf also nailed the Trump Industrial Complex wherein the media wrings its hands over the president while gleefully amping his every movement for profit: “He’s helped you sell your papers and your books and your TV. You helped create this monster, and now you’re profiting off of him. If you’re going to profit off of Trump, you should at least give him some money, because he doesn’t have any.”

But a year later, the post-game analysis remains critical of Wolf’s purported woman-on-woman comedy crimes—not against Maddow or Mika Brzezinski but Sanders.

“We are graced with Sarah’s presence tonight,” said Wolf. Sanders sat a few feet away. “I have to say I’m a little starstruck. I love you as Aunt Lydia in The Handmaid’s Tale.” The room grumbled at the reference to a character who delights in oppressing other women. Wolf pressed on. “I actually really like Sarah. I think she’s very resourceful. She burns facts, and then she uses that ash to create a perfect smoky eye. Like maybe she’s born with it; maybe it’s lies. It’s probably lies.”

Wolf left the stage to a confused reception. Then the social media monsters began breathing napalm.

The Hill called her “fame-hungry” and The Hollywood Reporter pushed out the headline MICHELLE WOLF GOES LOW WITH RAUNCHY HUMOR. Trump trashed her—which was to be expected—but then women in the press began coming to Sanders’s defense. NBC majordomo Andrea Mitchell said Wolf owed Sanders an apology. New York Times reporter and Trump whisperer Maggie Haberman tweeted, “That @PressSec sat and absorbed intense criticism of her physical appearance, her job performance, and so forth, instead of walking out, on national television, was impressive.”

Haberman’s remarks earned the biggest eye roll from Wolf. “She’s part of the problem; she’s 100 percent access journalism,” Wolf says, taking a sip of her drink (prosecco mixed with Aperol) and shaking her head in wonder. “Like Andrea Mitchell, Mika Brzezinski—they all came out and said things, and I was like, No, you guys just want to maintain your access—especially Maggie. She’s working on a book. They also had to say it to take attention away from my calling them out for using Trump to make money.”

Wolf points out that Sanders didn’t stand earlier in the ceremony when reporters received awards. She explains that she wasn’t making fun of Sanders’s appearance; if Wolf regrets anything, it is not adding an extra beat expressing her sincere appreciation for Sanders’s makeup. (Sanders politely declined Playboy’s request for comment.) She also notes that no one complained about her jokes citing Paul Ryan’s lack of balls and Chris Christie’s weight.

“What still bothers me is the way so many in the press criticized her,” Meyers says. “She wasn’t a contest winner. She was a comedian they hired based on her body of work. Why should she tamp down her style to fit some weird idea of decorum most people don’t care about?”

A month later Netflix premiered The Break With Michelle Wolf, which she executive produced. Some say Wolf’s set was designed to drum up excitement for her show, but with only a 10-episode order—consider how many shows Conan O’Brien needed before he got good—The Break had little chance to succeed. It has some bright moments, however, including her roast of the comedic political lectures popularized by John Oliver’s Last Week Tonight and Meyers’ Late Night segment “A Closer Look.” On The Break, Wolf skewers the format, calling hers “Segment Time.”

“It doesn’t necessarily make you think more or change your opinion at all,” says Wolf of the format. “It just reinforces what you think, and we’re living in a climate right now where things are so off-balance that people just want someone to say a logical thing. I don’t think that’s the right way to do comedy.”

She starts to laugh.

“But they still have shows, so what do I know?”

The great irony in Wolf being trashed by powerful women is that she has built her entire career highlighting, in a sometimes graphic manner, how unfair life can be for women, whether it’s working mothers or Hillary Clinton. On her HBO special, she says, “If you’re a woman in power and think you’re well-liked, you are so wrong. There are e-mails to prove it.” She has described HRC as unlikable—the kind of person you run to the bathroom to avoid at a party. But she believes that’s how a woman in power has to be. She will never come off like a good old boy.

“I would have loved if Hillary had been like, ‘Hey, you guys are being real sexist talking about my smile, and yeah, I fucked up on the e-mails, okay, but I’m a grandmother, and I know what I’m talking about. I’ve been here forever. I’m super qualified,’ ” she says.

I ask Wolf if she’s had feminist mentors. “That’s an interesting question. I don’t think I’ve ever been asked that,” she says. Instead of naming a comedian or an author, Wolf focuses on her childhood in “the middle middle class” of Hershey, Pennsylvania. She idolized her two older brothers and wanted to go wherever they went, which meant pretending she was one of the dudes. “I don’t even think my brothers knew I had a period,” Wolf says. “It was one of those things where I was just trying so hard to fit in with the boys that it was like, They can’t hear about this.

We fell in love with her lilting, almost hypnotic voice.

Unlike Chris Rock, who was doing stand-up in his teens, or Judd Apatow, who interviewed comedians at the comedy club where his mother worked before his testicles had dropped, Wolf came to comedy later. She grew up a track athlete and cites that as a source of motivation when trying to write new jokes. (“You might have set a personal best, but they just move the bar higher until you fail,” she says.) She went to the College of William & Mary, joining a track and field team there, but injured herself; that ended her sports career.

It left her wondering what to do next. The first thought wasn’t comedy. “I knew I wanted to make money,” she says, citing a comfortable childhood during which she was surrounded by friends who were supremely more comfortable than she. After graduating with a kinesiology degree, she went to work at Bear Stearns during the Great Recession and saw older colleagues lose everything. To this day, Wolf doesn’t trust the stock market; her money sits in a noninvested Schwab account.

She went with friends to a taping of Saturday Night Live and was hooked. She started taking improv classes and switched to stand-up about seven years ago. She eventually got noticed by Meyers. “Everything about her path to comedy seemed like it would be a plus for us—passionate, hard worker, risk-taker,” he says. “Plus we fell in love with her lilting, almost hypnotic voice.”

Wolf worked for Meyers for two years before Trevor Noah poached her. While she takes pains to point out the men who’ve helped her, she recognizes it wasn’t a level playing field.

“There are plenty of male comics who have kids and go on the road. Women wait to have kids later, when they’re more successful and can afford help,” says Wolf. One of the other double standards that chafes her is what she perceives to be a woman’s need to answer for a man’s behavior. Recently, Wolf encountered picketers after appearing on a bill at the Comedy Cellar with the dethroned Louis C.K., someone Wolf once opened for on the road. She endured women asking how she could call herself a feminist and have her name on the same show as the serial masturbator.

“Journalists just want a headline about Louis, and to me, that’s not helpful and definitely not my responsibility,” says Wolf. This is the only moment during our interview that she gets testy. “It’s not my job to clean up the mess of something a man did. I’m not going to sacrifice my spots at a place where I’m most productive just to prove a point that’s not going to go anywhere.”

This year, Wolf has indeed not sacrificed her spots. She’s touring the U.S. through May and hops overseas this summer. She has auditioned for a few acting roles, but most of her time is spent working on her next special and tour. She recently ran a 50-mile ultra-marathon and found herself turning jokes over in her mind until mile 42, when she nearly passed out. “You have to keep moving or it can all go away,” she says.

I’m not supposed to be your moral compass. I’m not supposed to be your philosopher.

And she watches the 2020 presidential race with trepidation. While her comedy features support for abortion rights and improving living conditions for mothers, she dreads any female candidate making that her platform when so many families struggle to put food on the table. “I hear Kirsten Gillibrand is going to run on gender,” she says. “That’s a terrible idea, because you’re going to get only the people who care about that. You can’t eat equality. You’re going to vote for the candidate who can get you a job.”

Wolf knows this sounds bad—perhaps slightly anti-woman. She faces her palms out in the universal “Who knows?” pose.

“I’m not supposed to be your moral compass,” she says. “I’m not supposed to be your philosopher. I’m not supposed to be your religion. I’m just supposed to be the person who says the thing that makes you laugh. And maybe makes you think differently.”

Wolf pauses for a moment, pushing back her straightened hair.

“But most of all, makes you laugh.”

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