Michelle Wolf Reveals Her One Regret From Infamous Trump Roast

Michelle Wolf is probably best known for being the comedian who roasted Sarah Huckabee Sanders to her face at the White House Correspondents’ Dinner in 2018. Seven years later, her only regret is that she wasn’t meaner.

In this episode of The Last Laugh podcast, Wolf reflects on how much—and how little—has changed since, from Donald Trump’s escalating attacks on comedians to her new identity as mom of two, which she explores in her new Netflix special The Well. She discusses her complicated reasons for turning down the Riyadh Comedy Festival, explains how her short-lived talk show The Break predicted Trump 2.0, and shares her take on the fragile state of late-night TV.

With the younger of her two small children in her lap, Wolf begins our conversation by saying that becoming a mother made her “appreciate stand-up” in a new way. “Being on stage is like a tiny vacation,” she jokes. “I’ve also become a much more efficient joke writer, because I have a limited amount of time to write jokes.”

Until this new special, Wolf was not known for sharing any personal details about her life on stage, preferring instead to comment on politics and the culture at large. But there was something about becoming a mom that made her want to relate more directly to her audience.

“Now I feel like I have an actual personal life to talk about,” she says. “Although you do see reviews from people that are like, ‘another comedian had a kid, and now they’re talking about being a parent.’ And it’s like, yeah, you mean one of the most relatable experiences a human can have?”

Below is an edited excerpt from our conversation. You can listen to the whole thing by following The Last Laugh on Apple Podcasts, Spotify, or wherever you get your podcasts, and be the first to hear new episodes when they are released every Wednesday.

You talk in the special about how you had your first baby when you were 37 and were already a successful comedian. And you say that you feel like you couldn’t have gotten where you are in your career if you had become a mom earlier.

Yeah, I mean, as a stand-up between touring and working at night and all that stuff, it’s nearly impossible to do it without an extensive support system. In order for me to go on a tour with a baby, it’s a nanny, which means more flights, more hotels, you’re just spending a lot more money. And earlier in my career, I wasn’t making that much money. I would’ve been spending at least what I was making just to do the shows. So the kind of grind that you have in stand-up, I don’t think I would’ve been able to do it. And even right now, I’ve got my eye on that private jet money at the moment. I know everyone can roll their eyes about rich people right now, but I’ll tell you what, if I can travel on a jet with two children, I’ll post my feet on OnlyFans for a little bit.

Well, I am curious how much of that went into your consideration about the Riyadh Comedy Festival. You were offered it, you turned it down, but not for the reason that people might think, right?

I didn’t have to make a decision. The decision was made for me. The show they offered me was on October 4th, and my due date was September 29th. So whether I wanted to do it or not wasn’t really part of the question. It would’ve been literally impossible. Had it been at a different time, I really would’ve had to weigh the pros and cons of it. Because they were throwing crazy money at people. And then, in your head, you’re like, well, maybe this opens up a whole new market for me. But I do think anything paid for by a government, that’s a hard one to do. And there’s a lot of countries like this, but Saudi—everything’s paid for by the government. You can travel to America and do a lot of things that are not sponsored and paid for by the government.

Yeah, people have been like, “our government’s doing bad things too,” but I think it would be just as problematic to go do some show that’s sponsored by the Trump administration.

Right. If I was getting flown to Mar-a-Lago, I’m pretty sure I would turn that down.

I do feel like with the Riyadh thing, you got the best of both worlds, because you didn’t have to make the decision. Then you also posted a video of jokes that you would’ve told at the festival that, as you put it, would’ve gotten you “Khashoggi’d.”

If I had decided to do the festival, I would have done jokes, like those ones I released, or very similar to them. I would’ve been like, I’ve got to throw at least one or two of those in there. So I think it’s best for everyone that I didn’t do it. But think a lot about people like Jessica Kirson, who people got really angry with, but she said, I’ll only do it if I’m allowed to be an open lesbian on stage. And they were like, OK. And I do think that’s important. I think what she did was a big deal. I think it was very brave of her. There were probably a ton of people there who had never heard a lesbian do comedy. And I feel bad that people got angry about that because I think that is breaking a barrier.

Your special, The Well, is not super topical, but then you also have your Instagram, which I’ve become kind of obsessed with, where you’re posting videos from your closet, or walking down the street, reacting to things that are happening in the news in real time. It’s interesting just to compare that outlet to something like your show The Break, which was obviously short-lived on Netflix and had a lot of high production value. Now, there are probably more people watching some of your reels that you’re putting up on Instagram than watched that show.

Yeah. I used to get paid thousands of dollars to do those shows. Now, more people watch them, and I get zero. But I understand what you’re saying. I do it in the hopes that I gain people who are like, I like her comedy. If you like this joke, then hopefully you’ll buy a ticket, or you’ll watch the special, or whatever else I might be doing next. And to be quite honest, I am at this point just trying to amass a following. And sometimes I put out jokes and people are like, “Ugh, unfollow.” And I’m like, good, get out. If it’s not for you, it’s not for you. I want my audience to be people that like my comedy. They don’t have to love every joke I do, but I don’t want to have to edit myself for my followers.

That’s how you get the following that’s going to keep following you, and want to go to your shows and all that.

Yeah. Because, all the political stuff changes over time. And you see that a lot with comics, especially with Trump, they really joined the Trump bandwagon. There were a bunch of those comic podcasters at the inauguration, and now they’re like, “wait, he’s doing all these things I didn’t think he would do!” He was very clear, this is what he was going to do. You liked this guy, and now if it’s hurting your business, you don’t like him.

That’s a reason to be true to yourself and actually think about what you believe and what you want to put out there.

Right. Because if you really believed in this guy and you believed in what he was doing, you wouldn’t be like, “I can’t believe he’s grabbing parents out of cars at school pickups and deporting them.” You would be like, well, I think it’s necessary. If that’s really where you were, I’d think you were a terrible person, but I’d also have more respect for you in a way where it’s like, well, at least he’s consistent. He’s not like a wishy-washy or doing it for the views or the money or whatever. Instead, they just like the idea of being close to power, which is, I think, what a lot of those guys get off on.

The Break came right after this big moment for you at the White House Correspondence dinner, which really defined your career for much longer than you probably ever thought that it would. With some distance now, how do you view that night and the impact that it had on your public persona?

I think if I could do it all over again, I would’ve been meaner. I would’ve gone harder. The jokes I said about Sarah Sanders weren’t actually mean. Everyone said I made fun of her appearance. I definitely did not. I complimented her makeup and said she told lies, which she does. I knew the points I was making, and I was very happy to make those points. But I also feel like I was fairly restrained. Had I known what the reaction was going to be and how strongly people would’ve reacted, I would’ve gone harder. If you’re gonna get mad at me for jokes, then let them actually be mean jokes. As far as roast jokes go, what I said about Sarah Sanders was very tame.

I think maybe the reason why the media focused so much on the Sarah Huckabee Sanders jokes was because she was right there. And it’s so rare for these people to get criticized to their faces, especially now.

She was right there, but she was right there in place of Trump. In a normal Correspondents’ Dinner, the comedian makes fun of the president, and then the president gets up and makes fun of everybody—including the comedian.

But that didn’t happen.

That didn’t happen. It was just me up there making fun of Sarah Sanders, who was there in the place of the president. And I would much rather tell jokes to someone’s face than behind their back.

I mean, now, not only are they not getting made fun of to their faces, they’re not even facing real questions from reporters.

Well, if you ask the president a question he doesn’t like, he is going to call you a piggy or ugly or whatever. And listen, if you get called ugly by Trump, you’re doing something right.