Why Michelle Wolf Quit Telling Trump Jokes—and Got Even Funnier

Matt Wilstein
The Washington Post via Getty

Michelle Wolf mentions the current president of the United States just once in her new Netflix special Joke Show. The punchline comes near the end of her masterful hour-long set—and she doesn’t say his name.

It’s been almost two years since Wolf broke into the stand-up mainstream with Nice Lady on HBO (deemed the best special of 2017 by this website) and just about a year and a half since she broke Washington, D.C., with her scathing White House Correspondents’ Dinner speech.

After Wolf joked that she loved Sarah Huckabee Sanders “as Aunt Lydia in The Handmaid’s Tale” and complimented her “resourceful” approach to makeup by saying, “She burns facts, and then she uses that ash to create a perfect smokey eye,” prominent media figures on both sides of the partisan divide denounced her and even the White House Correspondents’ Association tried to distance themselves from her. They haven’t invited a comedian back since.

The controversial performance dramatically raised Wolf’s profile and drew outsized attention to her “late night”-style series The Break, which premiered exactly one month later. But when Netflix prematurely canceled it after just 10 episodes, Wolf decided to rededicate her energy toward stand-up.

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After years spent writing for Late Night with Seth Meyers, helping Chris Rock with his “sorority racist” Oscars monologue, and then serving as a contributor on The Daily Show with Trevor Noah, 2019 was the first year during which she only did stand-up comedy.

“It’s probably been the best year of my life,” Wolf says.

Ahead of the new special’s release on Dec. 10, we talked to Wolf about everything that has gone down over the past two years and why she decided to stop telling Trump jokes after the White House Correspondents’ Dinner.

So it’s been about two years since your last special, you had a very big 2018, and then we haven’t seen you for a while. Does this new special feel like a comeback of sorts?

Maybe a little bit. I’ve gotten to spend this last year just doing stand-up for the first time in my career. And I’ve had so much fun. It’s probably been the best year of my life. And I think it’s also reflected in the special. I think you can tell I’m having a good time. I know a lot of people loved me from the Correspondents’ Dinner, I know a lot of people hated me from the Correspondents’ Dinner, and I just hope when people watch this special they just get converted to fans of my comedy.

Your new special opens with a joke about otters raping seals, which is very funny but also makes a larger point about outrage culture, which has become such a big topic in comedy right now. Why did you want to open the special with that?

After I shot my last special, I went away for a week and that’s when I actually saw otters. And I put something in my Instagram story and that woman replied with what I say in the special. And as soon as she did that, I was like, right after taping my last special, I guess I have my first new joke. So it felt sort of fated. But then the more I worked on the joke the more it felt like an appropriate way to introduce comedy right now. We can’t wait to get angry at people. And I get it. I get why people get mad. I get why people like to scold. It gives you a sense of power. This “cancel culture” or whatever it is, this isn’t new. It’s literally been happening forever. There used to be stonings, beheadings, burnings at the stake, gladiators. We’ve always liked watching people die, whether it be literally or now more figuratively. And I think part of it is because in those moments, when you’re watching someone’s head get chopped off, you’re thinking, “Well, my life is terrible, but at least I’m not that guy.’”

You’ve obviously had that experience yourself of being, if not “canceled” then at least having people go after you for something you’ve said. What does that feel like for you?

Honestly, it was kind of nice. I think I spent too much time hoping everyone would like me. And then as soon as people hated me, there was so much freedom in that. Because you’re like, right, I’m not going to try to make everyone happy. That’s a crazy thing to do. So I’m just going to do the stuff that makes me laugh and hopefully the people that have similar sense of humor or appreciate jokes, that it also makes them laugh. But it’s really made me less cautious and more bold.

In this new special, you deliberately don’t tell jokes about Trump or really politics more broadly. What prompted that decision?

Doing the Correspondents’ Dinner, people just assumed that I was a political comedian. And it’s a weird thing to make an assumption about, because I was hired to do a job; a job I’m still very proud of, and a job that—I don’t think they thought I was going to do it that way. But I can write jokes about any subject. You give me a subject and a half-hour, I’ll give you 10 jokes. It doesn’t mean I’m a political comedian, it just means I know how to write political jokes. But they’re also not my favorite type of jokes to write. I like more social commentary, and of course those end up being political issues as well but that’s only because life is political. I also find political jokes, at this point, to be kind of boring and just so one-note. I’m just so sick of hearing about it. It doesn’t interest me to do it right now. I’m not saying it won’t in the future but it’s not my favorite topic.

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You worked on Late Night with Seth Meyers and then The Daily Show with Trevor Noah and both of those shows, along with Stephen Colbert and Samantha Bee and John Oliver and so many others, are almost all politics now and commenting on the news of the day. Now that you have some distance from it, what do you make of that at this point in the Trump administration?

I don’t really watch that much of it anymore. But I actually feel like late-night shows actually became the most accurate news sources at some point. The Daily Show went from making fun of the news in its original Jon Stewart form to now being a format that several shows do. Instead of making fun of the news, they’re actually giving you the news and just writing punchlines throughout it. I know people that work at those shows that are fact-checkers. Those shows are trying very hard not to say something that’s inaccurate. And that is not something the news is doing right now. We’re just in this political soap opera right now. There are things that are happening that the news is refusing to talk about. I brought up at the Correspondents’ Dinner that Flint still doesn’t have clean water. That was a year and a half ago and Flint still doesn’t have clean water. We shouldn’t be dissecting three hours worth of what Trump tweeted. We have 24-hour news networks, we have enough time to cover everything.

Yeah, I mean, this is something that you talked a lot about in the Correspondents’ Dinner speech but it did get overlooked because of the controversy surrounding the Sarah Huckabee Sanders jokes. Why do you think that played out the way that it did?

I honestly think the media heard what I said [about them] toward the end of the speech and wanted to avoid making that the story. So they made it about the joke about Sarah’s eye shadow. I think they were trying to distract from the fact that I said they are profiting off of [Trump]. He is helping them sell everything, from TV to books. The environment at the Correspondents’ Dinner was one of the most disgusting things I’ve seen. [CNN President] Jeff Zucker saw Kellyanne Conway from across the room and they both greeted each other like they were old friends having some sort of joyous reunion. He’s like, “Kellyanne!” and gave her a big hug. You guys pretend to hate each other, but you’re making so much money off of this relationship at the detriment to everyone else. It would be nice if they were willing to put their morals and values before money.

And seeing that, did you feel a little bit better about what you were about to say?

Oh yeah, as soon as I saw that I was like, I could have been meaner.

Yeah, I still maintain that your Kellyanne Conway jokes were just as mean as your Sarah Huckabee Sanders jokes.

First of all, I literally said I hope you get stuck under a tree. [The full joke: “It’s like that old saying, if a tree falls in the woods, how do we get Kellyanne under that tree? I’m not suggesting she gets hurt. Just stuck. Stuck under a tree.”] But I also specifically took out a joke about Kellyanne Conway’s looks because I didn’t want to make it about her looks. Had I known they were going to have a pretend outrage over a joke about looks that wasn’t about looks, I would have kept it in.

And it wasn’t just the right that was outraged about it. There were all these tweets that got a lot of attention from reporters like Maggie Haberman and Mika Brzezinski and Andrea Mitchell really criticizing. How did you take that at the time?

To me, that was so transparent. Of course Maggie needs to be outraged by this, because how else is she going to maintain her access? She’s working on a book right now. She’s doing all of this so she can raise her profile and make more money. Same with Andrea Mitchell. They needed to say that to keep their position. And also, I think I responded to Maggie; I said something along the lines of, this is about her eye makeup and her ingenuity of materials, but it sounds like you thought it was about her looks. I said she has nice eye shadow and everyone heard, she’s a pig! You heard that because you wanted to hear that. I did not say those words and my intonation didn’t even imply that. You want to look at some ugly people, there’s plenty of other people we could point out in the administration that are very, very bad-looking.

I actually interviewed Ann Dowd, who plays Aunt Lydia on The Handmaid’s Tale, a couple of months after the dinner. And she basically said she was totally unaware of it at first and then found the whole thing “completely surreal.”

I felt so bad because I was like, “Oh my God, I hope Ann Dowd doesn’t think I’m saying she’s unattractive!” I think Ann Dowd is, first of all, beautiful, but also an amazing actress. And I saw her at the Emmys and it was the first time I’d seen her since any of this happened and I was like, “I’m so sorry, I love you!” And she was just laughing about the whole thing, saying, “I didn’t take it badly at all.” Her character is horrendous, but she’s beautiful.

After you did this, the White House Correspondents’ Dinner has been effectively killed or rather you killed it, because they haven’t invited a comedian back since. What was your reaction to that when they announced they wouldn’t be having a comedian anymore?

I thought, good. First of all, there’s no point in doing it if the president’s not going to be there. And roasts in general aren’t good if the home team’s not on board. The whole point of a roast is that everyone’s in on it. And this administration isn’t one that likes to be in on it. And honestly, they don’t deserve to be. If they had done the Alec Baldwin roast and he had been sitting with his arms crossed with a mean look on his face the whole time, it wouldn’t have been a fun event. But he got made fun of, he laughed, he made fun of people. That’s how roasts work. And maybe that’s what the Correspondents’ Dinner used to be, but I think we’ve moved so far away from that and the relationship between the media and the White House has gotten so perverted almost that I don’t think they should have it at all. I was very happy to burn it down.

Michelle Wolf is feted at a White House Correspondents' Dinner after party on April 28, 2018, in Washington, DC.

Tasos Katopodis/Getty

Your performance at the dinner really propelled you into your Netflix show The Break, which was then prematurely canceled after just 10 episodes. What do you think happened and would you do anything differently if you could do it over again?

I think one of the big things with that show is, we always knew 10 episodes wasn’t going to be enough. So we just kind of tried to have the most fun that we could in the time that we had. Had we originally been given more episodes—had we been given 32 like Hasan [Minhaj] had—I think we could have really figured out more of what exactly the show was. But it takes time for a show like that to find its feet. I’ve worked on Late Night, I know for Seth we were still figuring out after a year and a half what works and what doesn’t. It’s an evolutionary process. After the Correspondents’ Dinner, I let that seep in to the show more than I wanted it to. I genuinely wanted the show to be a “break” and just be silly and funny but that didn’t seem to be what people wanted at the time. People wanted me to talk about politics and those big, hot-button issues. That being said, I’m not unhappy with anything we did. I look back on some of the stuff and I think it’s very, very funny.

Well, now you get to be back doing stand-up and talking about whatever you want.

Yeah, the show ended and people were like, she’s over! You mean I get to go back to my favorite job in the world?

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