In the past 35 days, Michelle Wolf has hosted the annual White House correspondents’ dinner, scandalised Washington DC, outraged the president, run a 50-mile ultramarathon, launched her own Netflix show, and turned herself into a household name. Yet “the hardest thing I ever did in my life”, according to the comedian, was none of these, but “getting myself fired on purpose.”
Five years ago, she was working for a tech company, but knew she wanted to be a comedian. The plan was to get paid for as long as possible, while she worked on her act, until they sacked her. “I don’t like being lazy, but I was like: ‘Just do less and less work.’ I was writing jokes all day, just constantly writing jokes.” She nearly lost her nerve when she received a formal warning. “It was the worst feeling. I hate disappointing people. I almost gave up then and there.” But she stuck at the plan, and “eventually I got fired, which was great”. She celebrated with cocktails.
“I couldn’t believe I went through with it. But I was like, No, you have to work for what you want. You don’t want to hurt anyone along the way, but you have to be selfishly on your agenda, and let people know what you want and that you’re going to go after it. I think it’s good to be very selfish and put yourself first, and as women we’re never really taught that. We’re taught the opposite. But it’s your life, you know. You don’t get another opportunity to do it, so you might as well get what you want out of it.”
Wolf worked the New York comedy club circuit hard, and within 18 months was a fixture on Late Night With Seth Meyers. In 2016, she was nominated for best newcomer at the Edinburgh festival, and joined Trevor Noah’s The Daily Show; last year she made her HBO debut with a standup show called Michelle Wolf: Nice Lady, and signed a deal with Netflix to develop her own show. So when her agent called her in March with an invitation to host the White House correspondents’ dinner, the 32-year-old wasn’t nervous. “I was, like, I’m going to do what I want to do for this dinner.”
Like many people in Britain, I’d never seen Wolf before she got to her feet in Washington and caused a global sensation. We meet three weeks later, in the New York offices of Netflix. If her comic persona is mildly awkward, in person she is unexpectedly glamorous – a sleek, feline column of New York sass topped with a corkscrew mane, more Debra Messing than the “grownup orphan Annie” character Wolf used to play for Seth Meyers. The cartoonish voice is unmistakable, however, simultaneously shrill and rasping. She had a joke in her HBO routine about inhaling helium only to discover her voice remained entirely unaltered, but apparently this was absolutely true.
She smiles a lot, but there is the same faintly dangerous air of menace that electrified her correspondents’ dinner performance. When I tell her that pretty much everyone I know has asked me to congratulate her on the performance, she thanks me but couldn’t appear to care less; when I ask how she felt after running 50 miles, she says: “Tired.” Although not unfriendly, the message feels clear: we aren’t here to make friends, but to work.
Tradition holds that the correspondents’ dinner host delivers a “roast”, a peculiarly American tradition whose closest analogy in British culture would be a best man’s wedding speech, minus the mutual affection. Wolf thinks she was booked because the mood of the #MeToo movement demanded a female host, and the White House Correspondents’ Association (WHCA) naively assumed: “Oh, she’ll be nice.” As Wolf joked in her speech, “They were like, a woman’s probably not going to jerk off in front of anyone, right?” With hindsight, they might have found that preferable.
An early line went: “Mike Pence is very anti-choice. He thinks abortion is murder, which, first of all, don’t knock it till you try it. And when you do try it, really knock it. You know, you’ve got to get that baby out of there.” Of the president’s daughter: “She was supposed to be an advocate for women, but it turns out she’s about as helpful to women as an empty box of tampons. She’s done nothing to satisfy women, so I guess, like father, like daughter.”
But it was the jokes about Sarah Huckabee Sanders that caused the greatest uproar. “I have to say I’m a little star-struck. I love you as Aunt Lydia in The Handmaid’s Tale,” Wolf told Trump’s press secretary, sitting just feet away, before adding, “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.” The room audibly gasped.
“Unfortunately,” tweeted a New York Times journalist, “I don’t think we advanced the cause of journalism tonight.” The president of the WHCA released a statement regretting that “the entertainer’s monologue was not in the spirit” of the group’s mission. Executives at CBS News threatened to boycott the dinner in future, Trump declared the “filthy” comedian had “bombed”, and Sean Spicer denounced her speech as “a disgrace”. Andrea Mitchell, the veteran NBC News correspondent, demanded Wolf apologise to Sanders and others “grossly insulted” by her speech, while MSNBC host Mika Brzezinski tweeted: “Watching a wife and mother be humiliated on national television for her looks is deplorable.” All of which Wolf finds baffling because, she says, she didn’t make fun of any woman’s appearance.
“I make sure all my jokes about women are about their abilities and people sometimes can’t wrap their heads around that fact. It’s like, She made fun of a woman, it must be about how she looks. No, it’s completely based on our abilities.” The only looks Wolf mocked were two men’s – Mitch McConnell’s double chin and Chris Christie’s weight, which no one seemed to mention or mind – and her own, joking of Trump’s counsellor, Kellyanne Conway, “She has the perfect last name for what she does. Conway. It’s like if my name was Michelle Jokes Frizzy Hair Small Tits.”
Does she think Huckabee Sanders was genuinely hurt? Wolf looks wearily doubtful. “I mean, I can’t imagine. You can’t get up and lie to people every day and then get upset by this.”
The press secretary’s relationship with the media is not famously happy, so I wonder why Wolf thinks journalists leapt so indignantly to her defence. “I think they were distracting from the end of the speech when I called them out for making money off of Trump.” Wolf had accused them of pretending to hate the president, adding: “But I think you love him. I think what no one in this room wants to admit is that Trump has helped all of you. 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.” This explains the press’s censorious disdain for her roast? “Yes, they were just maybe trying to distract from that.”
I’d like to explore this theory, but Wolf’s body language is closing the conversation down. She looks faintly bored by talk of the dinner, as though it were of only very minor significance and already firmly in the past. When I ask how she felt before giving the speech, she shrugs.
“I really wasn’t nervous about any of the jokes. I knew everything else I had coming up after it, so in my head I was like, I’ve got to get through this because I’ve got to write those jokes for Tuesday.” Due to record the first test show of her new Netflix show on the Tuesday after the dinner, then fly to Utah to compete in the 50-mile ultramarathon on the Friday, “I was like, I have so much to do,” and she starts to chuckle, “Can we get on with this, OK?”
Afterwards, when she checked her phone, “A lot of my friends were texting me, and I kept seeing things on Twitter. But then I thought, I’m not going to look at this any more.” The following day she defended her performance with three brief tweets, but says she’d stopped following Twitter closely more than six months ago. “What I like about standup is that you tell a joke, and people laugh or they don’t. On Twitter it’s like, you tell a joke, and people try to either correct your joke or complain about it. You know, we’re all spending way too much time on social media, and I thought, ‘This isn’t good for my brain, I’m just going to work on the jokes I’m going to tell in front of people.’”
She didn’t consider the correspondents’ dinner the biggest performance of her career? She looks puzzled. “Oh, no.”
The nonchalance seems so implausible that at first I’m tempted to think it disingenuous. Fellow comedians were quick to come to Wolf’s defence, with Trevor Noah observing sarcastically, “Comedy isn’t just about jokes. It’s also about being polite and respecting authority. Unfortunately, it seems that some comedians, like Michelle Wolf, don’t understand that.” While Judd Apatow mocked the outrage with: “It’s like going to a Billy Joel concert and being shocked he played Piano Man.” Wolf concedes that she found their support “heartwarming”, so I wonder if she was more shaken by the furore than she cares to allow – or even frightened. After all, I point out, most people who find themselves at the centre of a blazing global controversy feel pretty jittery. She gazes at me with a cool, blank stare.
“I don’t mean to keep saying it, but I was so busy that I really wasn’t paying attention.”
Keeping busy has always been Wolf’s strategy. “I kind of just bog myself down with all the work,” she grins, “then I don’t have to worry about anything.” She grew up in a modest Pennsylvania town, a high-school athlete and straight-A student. “I always did really well at things. I was very competitive with my grades, I did really well at track. I was always a very nose-to-the-grindstone, head-down person.” She watched “a ton of Saturday Night Live, and The Carol Burnett Show, and Mary Tyler Moore, and on Mondays at school I would act out SNL sketches. So I always loved comedy. But in my head it never seemed like a viable career path.”
With no family connections to showbusiness – “God no, my uncle’s a sheep farmer” – she studied exercise science in a tiny town in rural Virginia, after which most of her college roommates were hired by banks. “Just get a job on Wall Street, too,” they urged Wolf. “We’ll live in New York for a couple of years, it’ll be fun.” So she did – but it wasn’t.
“I almost immediately hated it. I really was very bored by finance. There’s a lot of yelling. There’s a lot of competitiveness. I’m totally fine with competitiveness,” she adds hastily, “but if there was a problem it wasn’t like, OK let’s fix it and learn how not to do it again. It was more, ‘How many people can we get mad at for this?’ That’s no way to live.”
Everything changed when a friend and Wolf went to see a live recording of SNL. “After that I was like, How did these people get this gig?” She Googled the SNL cast, discovered they’d all stared out in improv, and promptly signed up to lessons. Within five minutes of her first class, she knew what she wanted to do with her life. “It sounds very corny to be love at first sight, but it was 100% love at first sight. This is it.”
She continued to work on Wall Street while taking classes, and in 2011 moved to the tech company, “basically doing admin”, while she honed her standup act. Comedy sounds not so much like a vocation as a compulsion for Wolf, and when she talks about its role under the Trump administration, she becomes intently serious.
“Trump jokes bore me. I think the problem is that we all keep confusing humour with facts, or with just pointing things out. People will say, Trump tweeted this, and then he tweeted this – it’s hypocritical! And people will be like, That’s hilarious! I’m like, That’s not hilarious, it’s just a pointing out of two things. There still needs to be a punchline. There still needs to be some sort of twist, or something. I always think of comedy as: it’s not what you want to hear, it’s what you didn’t know you wanted to hear. You should be surprised by what people say, and hopefully delighted, but it shouldn’t be the thing that you’d already thought of. Yet there’s this whole section of political comedy that’s just saying the thing that we want to hear, rather than pushing our brains.”
Wolf’s self-image seems to be firmly that of an outsider. She doesn’t have political friends in Washington, or inhabit the paparazzi-ed world of public celebrity; her social circle consists chiefly of New York comedians, such as Dan Soder, and revolves around work. There is no boyfriend, her name does not trouble the gossip columns, and there is nothing elite about her biography. Likewise, there was nothing cosy or clubbable about Wolf’s correspondents’ speech, so I wonder whether she worries about humour creating a comfortable illusion of subversion, while actually functioning as a safety valve. By laughing at Trump, are we enabling him?
“I think there’s never a bad time to make a joke.” She laughs mischievously. “I mean, there are definitely times where I’m like, I know I shouldn’t make a joke right now, but I’m going to remember this joke I have and tell it to my friend later. You know, when someone just said something really sad and you’re like, I’m going to comfort them as a person – but later I’m going to tell them the joke that this made me think of. So I don’t think it’s weird that we’re making jokes. I think it’s weird that Trump doesn’t have a sense of humour. It’s so alarming never to see someone laugh. It makes me feel sad for him. Just have a go at it! But I just don’t think he would understand a joke.
“So it’s fine for us to laugh, and it’s fine to make jokes and stuff. But also: vote, you know? Remember why we got into this, and how we can get out of it.”
It’s a signature segue, from playful teasing into political earnestness. She deployed the technique towards the end of her correspondents’ dinner speech, when she accused the media of profiting from Trump, and she wasn’t joking. “I mean, yes, we’re all addicted. The news makes money off the ratings, and I think we’re all partly responsible, too, because we keep watching it, and so it’s this vicious cycle. Of course they’re going to keep talking about everything outrageous that is happening, because we keep tuning in. But they’re not doing it to present the news; they’re doing it to present a show of some sort.” Would that be true of The Daily Show, where she worked until last December? After a brief hesitation: “Yes, totally.”
It’s partly because of this that Wolf’s new show on Netflix will not be particularly political. “I feel like everyone is doing politics right now, which is exactly what I’m trying to avoid with this.” The Break is a weekly blend of sketch shows, monologues and studio guests, the title advertising its intention to give viewers a break from the relentless commentary about political headlines. “It just feels we keep talking about the same thing, when there’s other stuff we could be talking about.” One of The Break’s test shows, she offers as an example, covered the Cannes film festival. “And I haven’t seen any other comedy shows really do that this week, so it was fun. There’s so much out there to joke about.” A whiteboard on the wall behind her is plastered in Post-it notes, alluding to topics The Break will cover, but security around the show is so tight that I’m forbidden to report them.
I ask Wolf about Louis CK, a comedian and friend she used to support on tour, before his career was derailed last year by sexual harassment revelations. In one of the weirder chapters of the #MeToo story, multiple female colleagues described CK engineering encounters where he would masturbate in front of them. Does she hope his career can recover? “I would like to see him come back and see if he’s evolved,” she answers carefully. Should he be able to joke about what he did? “I hope so, yes.”
Opinion is divided within the comedy world whether the #MeToo movement can be joked about, but Wolf is very clear. “I know there’s always people that say you can’t joke about this, or you can’t joke about this. But that’s always until you hear someone do it well – and then you’re like, Oh, they could joke about that. When you’re making jokes about hard subjects, the bar is very high. I equate it to an exercise metaphor, like a gymnast landing a really complicated vault. It’s going to take a lot of time to come up with a thing that the majority of people find funny – it’s a very high bar of difficulty. But if you can get it,” and a hungry smile slowly spreads across her face, “that’s pretty great.”
I sense Wolf growing impatient to get back to work. I’ve seldom met anyone more formidably focused, and find myself reflecting on a line from her Michelle Wolf: Nice Lady routine. “Nice ladies aren’t in charge of things,” she observed. “And if you’re in charge of something, and you think you’re a nice lady – no one else does.” Having loved her correspondents’ speech, I’d been a little disappointed to find Wolf difficult to like, but now see the absurdity of this.
I ask if she thinks nice and funny are mutually exclusive. She considers the question carefully. “Well, I think comedy needs to be honest and a lot of times people say they want honesty, but when they hear it they’re like, Oh, that was a cold slap of honesty. You know, being honest isn’t being nice.” So she doesn’t mind if people say she isn’t nice, as long as they think she’s funny?
“Totally, yes, yes,” she nods. “If you think I’m nice, great – but I don’t care.” She allows a throaty laugh. “My job isn’t to be nice. It’s supposed to be funny.”