Michelle Wolf just got her makeup done, but she's not wearing a perfect smoky eye crafted from the ashes of lies, like Sarah Huckabee Sanders in Wolf's now-infamous 2018 White House Correspondents' Dinner speech. The comedian is standing in the bright, exposed-brick New York office of her Netflix show The Break, surrounded by maroon chairs that look like thrones. A framed poster for her weekly late-night style show, in which she sits on a desk wearing her trademark platform sneakers in front of a cityscape, leans against the wall, still encased in plastic despite the fact that Season 1 wrapped a month ago.
It's been a wild few months for the former Daily Show correspondent, so it's understandable that hanging a poster up isn't at the top of her to-do list. Though her jab at Sanders' smoky eye was the joke heard around the country at the White House Correspondents' Dinner, Michelle Wolf's swift rise to fame was hardly an accident, though her path to getting there was atypical. It's hard to believe that a former college track star who majored in kinesiology and worked in finance until 2013 could so quickly be anointed the future of standup comedy, but watching Wolf onstage or screen is enough to make you believe.
It's a whirlwind trajectory, but Wolf is nothing if not doggedly determined in everything she does (this is a woman who ran a 50-mile ultra marathon weeks after the WHCD to decompress). In both real life and her comedy, she's unapologetically career-focused; she's constantly challenging society's notions of what it means to be a woman in 2018 by discussing things like her personal choice not to have children and "have it all." At every turn, Michelle Wolf's conversation with Bustle is thoughtful yet unexpected, which is exactly why she is one of our 2018 Rule Breakers.
Samantha Rollins: Your comedy is funny, but as we’ve seen through The Break, your HBO special Nice Lady, and your White House Correspondents’ Dinner set, it definitely is at its best when it’s making people laugh because they’re uncomfortable. Is making people uncomfortable in comedy the goal?
Michelle Wolf: I think that’s a side effect of funny stuff. Any time you’re pushing the envelope a little bit, you’re taking people out of their comfort zone. You want them to think slightly differently, and I like making people be like, “I never thought about that before.”
SR: Is that what men say to you after sets where you make extended period-fart jokes?
MW: I think most of them know [about periods]. It’s just like, it’s never verbalized to them. I grew up with two older brothers. You know, they were gross, and so I was gross. We used to fart around each other all the time and it was always very funny to me. Like, I still think farts are funny. I’ve never been a buttoned-up lady, you know? This is just who I am.
I would genuinely love to get to a place where women aren’t valued on our looks so that we can make fun of them for their looks. 'Cause we’re all crazy. We all look crazy. Everyone has something about them that is weird.
SR: Speaking of being a “lady,” your HBO standup special is called Nice Lady. What does the idea of being a “nice lady” mean to you?
MW: I feel like being a nice lady is being the kind of lady that society wants you to be, which I think is not good for women and growth and being good at a job. You know, like they want to put you in a box and treat you a certain way and kind of handle you with gloves. Like, “Oh, she’s a woman. She’s delicate.” And I’m like, “I’m not, and I will roll around in the mud. I don’t care. I like it.”
SR: In terms of being treated differently as a woman, with time to reflect on the backlash to your set at the White House Correspondents’ Dinner, do you feel the response was gendered?
MW: I mean, honestly — and it sounds like a canned answer — but because we just finished these 10 episodes of [The Break] and I went right from the Correspondents’ Dinner to our first test show, I was too busy to even deal with most of it. I don’t check social media that much. Every once in a while [when] something catches my eye I will, but I don’t think reading reviews is necessarily a good thing to do or a healthy thing to do. So, I don’t know. I do think people never expect women to be blunt, but Wanda Sykes had a really good [WHCD set] years ago where she was fairly blunt and I think it was just like before Twitter [became popular] and stuff like that. So I don’t think as many people got mad — they didn’t have a place to get mad about it.
I just want to write the best joke. So, sometimes it’s really mean. Sometimes it’s not. But whatever the best joke is, I’m not going to take their feelings into consideration because I certainly don’t think they’re taking our feelings into consideration.
SR: Do you feel your set was different than what comedians always do at the Correspondents’ Dinner?
MW: I do think it was. I mean, I think it was in a similar vein to what Colbert did when [George W. Bush was in office] — and then for a while, we had Obama and it didn’t seem like such a dire time, you know? So it was like, “Yeah, I can make jabs. I can do, like, lighter jabs.” And now it’s like, “Why am I going to go easy on these people that do terrible things?” I also just want to write the best joke. So, sometimes it’s really mean. Sometimes it’s not. But whatever the best joke is, I’m not going to take their feelings into consideration because I certainly don’t think they’re taking our feelings into consideration.
SR: You've said that you deliberately avoided making jabs at women's appearances in the WHCD set, though you made fun of Chris Christie's weight and Mitch McConnell's neck that night. Do you feel comfortable exploiting the double standard between making jokes about a woman’s appearance versus a man’s?
MW: I, in that instance, didn’t want to make something about people’s looks because, first of all, I feel like there’s — especially with Sarah [Huckabee Sanders] — there are so many worse things to go after. I don’t care how she looks. What she’s doing is awful. And so I didn’t want to make it about how she looked. But also, so much of our value [as women] is put on our looks, which I hate and I want to get past that so we can start making fun of how women look. Like, men aren’t valued on their looks, so you can make fun of their looks. It doesn’t matter. It’s not going to affect them. Their looks don’t keep them from jobs or marrying gorgeous people. I would genuinely love to get to a place where women aren’t valued on our looks so that we can make fun of them for their looks. 'Cause we’re all crazy. We all look crazy. Everyone has something about them that is weird.
SR: What did it feel like, to identify as a feminist and then have people say — whether it's founded or not — that your set was anti-feminist? How do you grapple with that?
MW: I mean, it’s clearly not anti-feminist. You know, like any woman being powerful is a good thing. As long as she’s not evil. Right now people are like, "Well, if you don’t support Sarah, you’re anti-feminist." And it’s like, no, if that were true, Hillary [Clinton] would be in the White House. You know, there were plenty of people on the other side when Hillary was running [who were] like, "I don’t have to support her just because I’m a woman." You know, you don’t. Being a feminist doesn’t mean liking every woman. It means equality. You don’t have to like people. You should just also think that it’s good when men and women are regarded as having similar brain power.
SR: Do you view yourself as a political comedian?
MW: I like to tell jokes that are more from a societal perspective. Everything is political because life is political. And things that affect us, like the rules that we live by, are made by politicians. So I just try to go after it more tangentially rather than hitting people over the head with it and finding things that no one else is talking about. Also, because I’m a woman, I kind of [have] more free rein to make fun of the women in the administration without coming off as sexist.
SR: The Break is one of the first late-night shows to debut on a streaming platform. How did being on Netflix influence the way you approached the show?
MW: People are used to watching TV in a certain way, especially these late-night shows where they’re formulaic in the structure. So we realized part of what we’re doing is teaching people how to watch the show. But it’s been so great because we don’t have to worry about sponsors. We don’t have to worry about cursing. Or, I mean, in the last episode we did like eight minutes on how crows have sex with dead crows, and I’m not sure we could’ve gotten away with that.
SR: Was that your idea?
MW: Yeah, I’m not sure we could’ve gotten away with that at a network. So, it’s perks like that.
This interview has been edited and condensed for clarity.
Hair: Bettie Rogers
Makeup: Katie Pellegrino at The Celestine Agency, using Charlotte Tilbury
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Bookings Manager: Guillermo Perez
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