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Michelle Wolf Is Ready to Do Her Own Jokes

The stand-up comedian made headlines—and a few enemies—with her speech at the 2018 White House Correspondents’ Dinner. Now, as the host of ‘The Break,’ she’s trying to reinvent the late-night show for Netflix. Here’s how one woman landed two of the toughest jobs in comedy.

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“It started off so nice and easy!” the comedian Michelle Wolf says, reflecting on her 2018 thus far. “I was on tour with Chris Rock in England, going to all these crazy places”—including Rock’s first Israeli show in Tel Aviv, or as Wolf told the crowd, “Miami’s much older sister.” “Then I get back,” Wolf says, “and in February I got hit with a bus.”

“Hit with a bus” is as fitting an analogy as any for landing two of the toughest jobs in entertainment at the same time—three, if you count the additional burden of splitting your time between them. First, Netflix ordered the new weekly series The Break With Michelle Wolf, tasking Wolf with breaking into the crowded ecosystem of late-night comedy while also figuring out how to make an old-school format work on a 21st-century platform. Then, Wolf became the latest in a long line of comedians to emcee the White House Correspondents’ Dinner—and the first to thoroughly puncture the dinner’s chummy collegiality between journalists and their subjects. “It used to be a dinner where everyone pokes fun at each other, but it was also in a much … light-heartier time? I don’t know what word I wanna use there,” Wolf reflects. “But now, I’m not going to pull any punches, because they’re certainly not.”

Wolf is certainly aware of the backlash that followed her April speech, but she also didn’t have time to engage with all the political hand-wringing. Instead, Wolf threw herself into The Break, which launched on Sunday with an episode that combined some elements expected of a late-night franchise (a topical monologue, a pre-released sketch) and some that are decidedly not (a riff about deciding not to have kids, a parody commercial about an Amazon Echo that demands lunch meat for no apparent reason).

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I speak with Wolf in mid-May at The Break’s headquarters in Hell’s Kitchen, a Manhattan production space with a storied history: Over the past couple of decades, it’s also been home to The Colbert Report, The Nightly Show With Larry Wilmore, and Wolf’s former workplace, The Daily Show, back in its Jon Stewart era. It’s about two weeks before The Break’s first episode goes live, and there’s a palpable atmosphere of sprinting to the finish line. Construction materials crowd the entrance to the studio next door, where Wolf had taped a test show the day before. Between interviews, Wolf and her producers are coordinating the release of The Break’s latest official trailer. The following Thursday, Wolf will record the in-studio portions of the inaugural episode, allowing a couple of days for “whatever magic Netflix has to put on it to make it available in 190 countries. Which is crazy,” Wolf adds, letting just a hint of awe slip into her voice.

For the most part, however, Wolf comes across as remarkably calm in the lead-up to a brand-new, still-unfinished show. “Literally what I pitched [Netflix] is very similar to what we’re doing,” Wolf explains. To viewers who first became aware of Wolf after she made headlines for either desecrating a hallowed Washington institution or speaking truth to power, depending on whom you ask, it might come as a surprise to learn that the founding vision for The Break doesn’t include taking on the White House week after week. “I feel like right now comedy’s kind of doing the heavy lifting in the news department,” Wolf observes. “And there’s plenty of shows that are doing that, and they’re all doing a great job. They don’t need another one. So I just wanted to come in and be like, ‘These are all jokes. None of this is for learning.’”

Not that Wolf plans to ignore current events entirely. The premiere’s monologue includes potshots at the NFL’s kneeling policy, and its desk segment begins by mock-praising new CIA Director Gina Haspel for “waterboard[ing] the glass ceiling till it broke.” “We’re not going to put our hands over our ears and pretend that what’s happening in the world isn’t happening,” says executive producer Daniel Powell, who also co-created the sketch series Inside Amy Schumer. “But she definitely doesn’t want to chase Trump, or make it be like taking down this administration’s going to be the goal of the show. She doesn’t ever want anything to sound like a lecture, you know?” Pivoting away from the headlines of the day also dovetails nicely with the almost unprecedented project of making a talk show work for streaming. Netflix has made the attempt only once before, with Chelsea Handler’s eponymous series. It’s very possible a historically of-the-moment genre can work on a medium built for on-demand binge-watching, but we’re still in the early days of streamers figuring out how.

While a late-night show may or may not be able to succeed outside of traditional television, it certainly can’t without a driving personality compelling enough to anchor a show. Whether writing for Late Night With Seth Meyers or serving as a writer-correspondent on The Daily Show with Trevor Noah, Wolf has continued to hone her own persona with her stand-up, culminating in the 2017 HBO hour-long special Michelle Wolf: Nice Lady. Wolf’s comedy is blunt, lewd, and often rooted in the messier parts of the female experience, from tampon-swapping to feminist infighting; now, her point of view finally has its own showcase. “I’ve written on late-night shows for the past four years, and I really like writing for other people,” Wolf says. “But it’s so fun, and I guess freeing, to just write for myself. I would always write the joke that everyone would laugh at and then be like, ‘We can’t do that.’ It was probably too mean or too weird or gross. So I’ll just do those jokes!”

For Wolf, now 32, comedy was not a lifelong dream. After growing up in Hershey, Pennsylvania, Wolf majored in kinesiology at William & Mary in Virginia before going into finance after graduation. It was only after attending a Saturday Night Live taping with friends, looking up where stars got their start, and enrolling in an improv class that Wolf started to consider trying to make being funny her job. Wolf has drawn on the pre-stand-up portion of her life in her act: “Honestly, I’ve never really been sexually harassed,” she told the audience at the Washington Hilton last month. “That being said, I did work at Bear Stearns in 2008, so although I haven’t been sexually harassed, I’ve definitely been fucked. That whole company went down on me without my consent.” Wolf may have left medicine behind, but you can hear her natural curiosity about how bodies work in an extended bit from Nice Lady on choosing not to have children: “You can grow a penis inside the vagina, like the world’s scariest greenhouse. … Me not wanting to have a baby is like a bird being like, ‘I’ll walk!’”

Wolf’s background has influenced her approach beyond serving as a wellspring of material. “A lot of jokes feel like math problems to me,” she notes. “Not even math problems—it does feel like an experiment, where you’re just like, Well, let’s try this. No, that’s not the right result. OK, let’s try this! No, that’s not the right result.” Amy Poehler has said that women in comedy tend to be, in scare quotes, “good girls”—driven and focused in a way that’s more class president than class clown. Wolf fits the archetype. “I always hate saying this because it makes me feel like I’m interviewing for a job, but I am a bit of a perfectionist,” Wolf says. “I really like making sure the joke is as good as it can be.”

In less than a decade, that commitment has yielded a distinctive voice, both figuratively and literally. “I took an aptitude test in seventh grade and it said my best profession was a clown or a mime,” Wolf recounted at the Correspondents’ Dinner. “Well, at first it said clown, but then it heard my voice and was like, ‘Or maybe mime?’” The Break opens with Wolf assuring the audience, “Yes, this is my real voice, so I’d like to welcome you and I’m assuming also your dogs.” Wolf has poked fun at her natural tone, high-pitched and nasal, before; my personal favorite moment from Nice Lady comes when she complains about men calling Hillary Clinton shrill, until it becomes clear she’s really talking about herself—a wordless pivot from political to personal that foreshadows The Break. In real life, however, Wolf considers her instrument an asset: “One of the reasons I love my voice is because I know it’s annoying. When I was editing my special, I was like, ‘I cannot believe people listen to me.’ But it catches your attention.”

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Some Wolf signatures are aesthetic. She almost always performs in sneaker wedges, which she favors because they give the boost of a heel while still being comfortable enough to perform in; during our conversation, Wolf is wearing a pair of black and gold Nikes that have gone out of production. (“I’m hoping the show does well enough that they’ll start making them again.”) And there’s the riot of curly, self-described “clown hair” that allowed her to play a character called “Grown-up Annie” on Late Night, the taming of which I’m disappointed to learn can’t be replicated at home: “My biggest secret is Betty, the woman who does my hair and re-curls every curl. There’s no way to naturally attain this. I just wanna put it out there. I am so fine if people get work done, I just wish they’d admit to it.”

Like her contemporary Ali Wong, Wolf is interested in the harsh realities of women’s bodies, which pack a comedic punch in part because they’re so repressed. “Women, we go through the grossest things all the time, and then we’re prancing around like it doesn’t happen!” she tells me. “I grew up with older brothers, so we were always farting. Periods are funny and happening all of the time. They are happening all of the time and we just go about our days as if they don’t exist, and it’s one of the most baffling things.” So she tells period jokes and fart jokes and occasionally, jokes that are both, sharpened with the focus of someone who squeezed a 50-mile ultra-marathon on the Bonneville Salt Flats in between everything else happening for her this spring. “I don’t know. I love it, and I make time for it,” Wolf shrugs of her running habit. “It’s how I get ready for something and relax and at the same time feel pumped up. It does everything for me.” A treadmill desk takes up a prominent corner of her current space.

“I’ve always considered myself a very hard worker, and it’s been very inspiring to now work with someone who has just a far more intensive work ethic,” says Powell. When the producer first watched Nice Lady, “I felt the same way I felt when I saw Bring the Pain by Chris Rock and Mostly Sex Stuff by Amy Schumer and New in Town by John Mulaney. Just like, ‘This is the next one of the all-time great stand-up comedians.’” Then he learned that, after Wolf already had the set written, she resolved to run through it 100 more times before she would tape.

“A lot of people say, when they do specials, ‘And then a week later, you think of a new tag!’”—a sort of grace note on a joke—“and I didn’t want that to happen; I wanted to explore every possibility,” Wolf explains. “And I never thought of a new tag! I feel like I explored every option on those jokes. I would never not do it that way.”

Wolf has likened booking the Correspondents’ Dinner to “a homework assignment,” and the preparation she describes is fittingly rigorous. “I hadn’t been writing for The Daily Show in two months, I hadn’t written a political joke in two months, and I was like, ‘Do I still have it?’ So I immediately sat down and wrote as many jokes as I could.”

The resulting speech rose to one of the toughest occasions in comedy: mocking a pack of self-important politicians and journalists to their faces. A friend texted Wolf shortly before the event: “Remember, if they’re cringing, you’re killing,” which proved prophetic for some attendees. With the strange logic that sometimes accompanies online outrage, critiques zeroed in on a handful of swipes at White House press secretary Sarah Huckabee Sanders. Wolf posited Sanders burns facts and uses the ashes to create “the perfect smokey eye”; she also compared the official, sitting just a few feet to her left, to Aunt Lydia from The Handmaid’s Tale, an enforcer who assists in other women’s oppression. The jokes led The New York Times Maggie Haberman to tweet in Sanders’s defense, while the overall performance prompted former Koch lobbyist Matt Schlapp to angrily walk out … and promptly report to an after-party. (The final section of Wolf’s speech, in which she took the media to task for profiting off the Trump spectacle, went largely unmentioned in postgame dissections.)

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Wolf mostly found the umbrage amusing; after Dennis Miller promised “a few brutally mean jokes about her by Wednesday,” her writers decorated the office for “Dennis Miller Wednesday,” though the jokes never came. She was nonetheless disappointed by a letter from WHCA president Margaret Talev that called her speech “not in the spirit” of the dinner’s mission. “I do think it was a shame that she felt pressured and then caved to that pressure,” Wolf told me. “Because I don’t think that’s in the spirit of the Correspondents’ Association.”

The event itself Wolf found “icky” and “gross,” a sentiment echoed by the staffers who accompanied her to Washington. “It was disgusting,” says head writer Christine Nangle. “People you would otherwise respect falling all over characters from the circus as if they were celebrities. Which I guess they are, but you would just hope people would have more dignity than they were.” Powell backs Nangle up: “We saw Michael Avenatti working the room like he’s a groom at a wedding. You’re seeing Jeff Zucker getting really chummy with Kellyanne Conway. It just made the entire media look like a charade and a farce, a sort of grand hypocrisy. Everyone thinks they’re Woodward and Bernstein, and they’re making all this money.”

“At one point they were like, ‘Do you wanna meet Kellyanne?’” Wolf remembers. During her time at The Daily Show, Wolf dedicated an entire segment to Conway’s falsehoods; at the dinner, she likened the name Conway to if she were called “Michelle JokesFrizzyHairSmallTits.” “I was like, No! Not even a little! I’ve never watched anything she’s done and thought, ‘I’d love to meet that lady.’”

Wolf closed her speech on a more somber note, by reminding the public figures in attendance that the city of Flint still doesn’t have clean water. “It’s that kind of stuff that actually angers me,” Wolf explains. “It’s like, yeah, sure, we can talk for three hours about what Trump tweeted, I’m sure it’s very important. But also, there are people in America that don’t have water.” The Break is not intended to be apolitical; a show that includes an unabashed critique of police brutality and institutional racism in its first 10 minutes is not a show afraid to pick a side. But Wolf doesn’t like feeling obligated to pick up her critics’ slack: “It’s kind of unfair that all of a sudden comedy has this responsibility to do the things the news should be doing. There’s a lot of shows that have taken on the responsibility, but they shouldn’t have had to.” Her Flint remark was sincere, but it was also a pointed rebuke to what her captive audience had let slide. “We’ve spent the last several years just talking about all this Trump nonsense and there’s actual, real things that are happening that are affecting people. That’s what journalism should be. It should be shining a light on the important things. And instead, they’re just gobbling up ratings.”

On Netflix, there are no ratings to chase, at least in the Nielsen sense. There are no sponsors, either, a perk Wolf gleefully takes advantage of in her first monologue: “Fuck you, Geico! Pick a mascot, ya hoarders!” There are also no commercial breaks or hard time limits or a nightly slot—many of the tried-and-true signals that tell late-night viewers how or when to watch. Fans of The Break can tune in as soon as an episode drops, at 12:01 Pacific time on Sunday mornings; they can cue it up over breakfast on a weekday; they can even binge a few episodes or skip around the catalog months down the line.

“We thought about all that stuff, even down to ‘Well, is it OK to have a show that feels like it’s happening late at night, but people could be watching it at noon?’” Nangle says. (“Late night” connotes a genre as much as a time of day, but The Break might nonetheless become the first late-night show to largely not be seen … late at night.) “We would be crazy not to [think about timing], especially for covering topical stuff.”

If one of the purposes late night serves, especially over the past couple of years, is to help viewers digest the events of the day or the week, The Break faces the unique challenge of crafting comedy that can accomplish the same thing without the shared reference of a news cycle. “You’re getting a take on current events, but there are other things in there that are probably more evergreen in nature,” says Brandon Riegg, Netflix’s director of alternative programming. “One of the sketches we released earlier, ‘[Featuring a] Strong Female Lead’”—where Wolf plays a gruff cliché of Olivia Pope–like hypercompetence who grunts catchphrases like “I have no time for emotion in my sex!”—“something like that can be consumed and appreciated at any time, and you’ll see elements like that within every show. It’s not super topical in the sense that it has a short shelf life.”

Ultimately, Powell recalls, the writers stopped trying to parse how well particular pieces would hold up over time and started abiding by the simple dictum of “Funny is funny”: “I grew up on early-’90s Saturday Night Live. I remember vividly watching reruns six, seven, eight months later. They would be hyper-topical when they came out, like a presidential debate that was months in the past, but it was still funny to watch Dana Carvey’s impressions.” There might not be breaking news about allegations of sexual assault against Mario Batali in the future, but the concept that Batali might be charged with “a pinch of misconduct, two tablespoons of making women uncomfortable at work, and three cups of having a ponytail and not playing the jazz saxophone” plays regardless of context.

In the absence of built-in structural guidelines, The Break imposes some on itself, like the fake, pre-taped Amazon ads that took the place of real ones. “We’ll have little interstitials instead of commercials because there’s no commercials on Netflix and we need a way to get from place to place,” Wolf says. “And for people’s brains. We’re so used to watching in a certain way.” Mostly, though, The Break’s creative team seems to enjoy the latitude they’ve been given. “Almost all of the stuff I’ve produced through the years has been for Comedy Central, and they have a very specific demographic,” Powell offers by way of contrast. “But because Netflix is for everyone, it’s not like, ‘You need to do more to service the male 18-24 demographic,’ which is so much of what I’d had to do throughout the years. This is more about, ‘What’s the best way to frame the show for success with the people we know would like Michelle?’”

Netflix releases so many series, features, and specials that it can prove difficult for individual projects to break through the noise, let alone stay present in viewers’ minds week after week. During Chelsea’s first year on the service, the show released three new episodes a week, but based on my own algorithm-curated homepage, I’d have had no idea it existed after the first few installments. Netflix has since released other talk-adjacent shows, like David Letterman’s interview series, My Next Guest Needs No Introduction, or the recently launched The Joel McHale Show With Joel McHale; these concepts are more specific than Chelsea’s Tonight Show–for-Netflix swing, though they also present similar challenges. “I think from a technical standpoint, we’ve gotten better at ‘How do we distribute these shows to all 190 countries?’” Riegg argues. If the algorithm works the way it’s designed to, whether you’re a Wolf fan or a likely convert based on your existing preferences, “the show will get promoted to you every week, whether you necessarily watch every week’s episode or not.”

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The benefits and drawbacks of Netflix as a distribution platform are admittedly wonky, and their intersections with The Break may not become clear for some time. For now, Wolf and her writers are focusing on what’s under their control. They’ve excised some classical talk show elements, like the one-on-one interview: “I’m just not great, in my mind, at conversation,” Wolf says. “Especially because this is more like a variety show, so I want [guests] to come on and do a bit that is just funny rather than have to tell a story they came up with their PR person or something.” (Plus, the less schedule-bound a show is, the less utility there is in movie stars coming by to plug their new vehicle’s opening weekend.) Wolf also enjoys shoring up her skill set by hiring writers with different comic backgrounds: “I’m definitely not the strongest sketch writer. I can write a billion jokes, but arc is hard. So we got some great sketch writers.”

But above all else, The Break is an opportunity for Wolf to play to her strengths. From the beginning, Wolf wanted her monologue to be styled more like a stand-up set—longer, looser, with the camera following her as she paces the stage with a microphone. Though she’s handling the transition to all-purpose host gracefully, Wolf is first and foremost a stand-up; true to her astonishing drive, she tells me that as soon as she gets used to The Break’s schedule, she plans on resuming weekend drop-ins at local venues like the Comedy Cellar. The format suits her. It also furthers the jokes-first mood she’s trying to create. The first thing The Break viewers will see every week is one woman, mic in hand, trying to make people laugh.

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