Michelle Wolf Knew Exactly What She Was Doing At The White House Correspondents' Dinner

As she ambled towards the podium for her stand-up set, those in attendance at the 2018 White House Correspondents' Dinner may have assumed Michelle Wolf’s enigmatic expression was merely down to nerves. With the benefit of hindsight, we now know that this was the look of someone preparing to whip up a worldwide shitstorm. It’s a tradition of the annual event to invite a comedian to throw a few satirical zingers in the general direction of the incumbent administration. But instead of the mild roasting most were expecting, Wolf lit the fuse on a blitzkrieg of white-hot burns that made headlines around the globe.

It also unleashed a torrent of outrage from both ends of the political spectrum, most pointedly directed at a quip about Press Secretary Sarah Huckabee Sanders: “She burns facts and uses the ash to create the perfect smokey eye.” In the days following, Wolf was forced to play damage control on social media, defending herself against confused accusations that she was attacking Sanders' physical appearance: “Those jokes were about her despicable behaviour, not her looks,” she says.

But in the hours before this now infamous blowtorching of Trump and his acolytes, only Wolf knew what lay ahead. “I went to do a soundcheck that afternoon, and the woman who was coordinating everything wanted to know what my gown was going to be like. And I was like, ‘Oh, I’m wearing a suit.’ And she replied, ‘Oh yeah, me too, I’m wearing pants too. It’s kind of like my little stick-it-to-the-man.’ And I just thought, ‘Ooooh. You guys literally have no idea what I’m about to do. I guess they thought there was maybe going to be this polite but funny woman, who was going to poke some fun at the room. But honestly, I went in there with every intention of doing exactly what I did. It wasn’t a surprise to me the reaction I got. That’s exactly what I was aiming for.”

While the response to her incendiary smackdown at the Correspondents' Dinner was by design, an unsolved mystery is the reason she was invited to perform in the first place. “I don’t do political jokes about politicians. Like, at all, when I do stand-up. I mean, I do have a distinct point of view on the world – I do a lot of jokes about healthcare and women’s issues and stuff like that. And I think one of the things people get confused about is that political issues are things we deal with in everyday life. But every once and a while I’ll get someone that yells out, ‘Talk about Trump.’ And I’m just like, why? All he wants is for us to talk about him, and the more we indulge that the happier he is! He doesn’t care if it’s good or bad. As long as we’re saying his name over and over again, he’s thrilled.”

Wolf may have fully expected to scandalise her audience, but one reaction she hadn’t banked on was shocked surprise at the risqué thrust of her humour. Those familiar with Wolf’s comedy know there are few lines she isn’t prepared to cross. Her maestro turn in 2017 HBO special, Nice Lady, was a symphony of fart jokes, testicle gags and gloriously gross yarns that spun an almost infeasible number of LOLs from the most puerile source material. That’s not to say that Wolf’s comic stylings are unrefined. In fact, it’s the sheer brilliance she applies to seemingly witless topics that has made her such a spitfire addition to America’s stand-up elite.

"I went in there with every intention of doing exactly what I did. It wasn’t a surprise to me the reaction I got. That’s exactly what I was aiming for."

However, it’s no mean feat judging just how far a joke can be pushed before it stumbles into the realm of the offensive. “It’s really just a matter of doing it over and over again and testing the waters,” she says of her fine-tuned ability to the toe the line between the risible and the revolting. “It’s one of the reasons I get so frustrated when the general public gets mad at comedians who are working on jokes. Because it’s like, ‘They needed you. They needed you to know if that was too far or not.’ The audience is our litmus test. Not every time a comedian walks out on stage is the show like, ready to tape as a special. There’s a very good chance when you go to a comedy show that there’s someone testing out a line, or seeing if they can approach a topic from a new angle. Because we need to know: does it make you laugh?”

While her brush with the White House may have been Wolf’s most talked about outing in 2018, it wasn’t the most personally significant. That honour belongs to her late night-style variety show, The Break With Michelle Wolf. The Netflix-produced series ran for just ten episodes before being cancelled. But while it may have not been around for a long time, it was definitely around for a good time, revealing Wolf’s talent for situational comedy and current affairs commentary, every bit as slick as the male-dominated big leagues of Kimmel, Fallon, Noah, Corden and Colbert. 

This is hardly surprising, given the pedigree of Wolf’s writing room experience, having plied her comic trade behind the scenes for Late Night With Seth Meyers and The Daily Show. But funny as she may be on paper, Wolf’s live delivery and her unique voice – dulcet tones that fall somewhere between Fran Drescher and Amy Poehler – would likely still have audiences rolling in the aisles by merely reading the phone book. “I wish I could say flat out that it’s a special skill that I have, but it’s really just how I talk,” she admits. “The more excited I get the shriller it gets. It’s just how it comes out: as soon as I get excited my voice just goes right up there. It’s probably not a good idea to bring a dog to my show, that’s all I’ll say.”

At the age of just 33, Wolf’s star is on the rise. But while there’s something undeniably fresh and invigorated about her comedy, which is rooted in a classic behind-the-mic format. There’s one simple reason why Wolf is something of a stand-up purist.

"I love punchlines. I mean you can talk about anything you want, but if you don’t have punchlines, that’s not comedy to me,” she says. “I think one thing that’s happening quite a lot in comedy at the moment, is people are confusing clapping with funny. Especially about things connected to the government. Someone can say something that’s just true, and people will confuse that with a joke. Like, ‘Donald Trump is bad,’ and everyone erupts in clapping. But that’s just saying something factual, you know. That’s not comedy, in my opinion. For me, the best comedy is something people didn’t know they wanted to hear."