IN CONVERSATION

Michelle Wolf Sounds Off on Ivanka Trump: ‘We’re All Fooled by Her’

The host of Netflix’s ‘The Break’ spoke with Marlow Stern about her exciting new talk show, the Trump administration’s comedy policing, and the problem(s) with Ivanka.

Tasos Katopodis/Getty Images for Netflix

In late December, I met Michelle Wolf at a trendy coffee shop downtown to discuss her first big stand-up special, Nice Lady. Over the course of an hour-plus, she opened up about her journey from college track star, to Bear Stearns, to Late Night and Daily Show writer, to rising comedy star.

We met at 8 p.m.—the only time she could squeeze me in between her day job at Daily Show and series of nightly stand-up gigs (she was, at the time, performing up to 25 shows a week). And, despite her wild red mane, shiny kicks and piercing voice—not to mention her stints opening for the likes of Louis C.K. and Chris Rock—went virtually unrecognized.

Quite a lot has happened since then.

Wolf’s landed a Netflix talk show, thus breathing the same rarefied air as mentors Seth Meyers and Trevor Noah; performed a dynamite set at the White House Correspondents’ Dinner, earning the ire of White House reporters and Trump administration officials alike; and debuted said show, titled The Break, to critical acclaim. Oh, and if all that weren’t enough, she ran a 50-mile ultramarathon out in Utah.

These days, Wolf is holed up in her New York office Monday to Thursday from 10 a.m. to midnight, hashing out new material for The Break—an exciting mélange of stand-up, sketches, and scripted guest spots. On Friday, she shoots a sketch, and then performs stand-up sets around Manhattan every Friday, Saturday and Sunday night. She is still the hardest-working woman in comedy. “I take, like, the day of Saturday and Sunday off… to get coffee,” she tells me, chuckling at the ridiculousness of it all.

The Daily Beast caught up with a very busy Wolf to chat about The Break and much more.

This interview has been edited and condensed for clarity.

I know the White House Correspondents’ Dinner thing has been beaten to death, but there is something poetic about how you and your mentor, Seth Meyers, were the two people who really managed to get under Trump’s skin at that event. 

[Laughs] I think it’s great. I also think it’s hilarious—and Seth pointed this out when I was on his show—that mine has more views than his. That’s always nice.

We’re all still waiting for Dennis Miller’s jokes about you.

I mean, I’d love to see them. I’d really love to see his analogies. [Laughs]

There’s this Samantha Bee dust-up over her Ivanka Trump joke, and it struck me as odd—the amount of attention being given to this one curse word in a lengthy bit about ICE cruelly separating children from their parents at the border. That focus seems rather narrow in the grand scheme of things.

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I think there’s a distraction method of Oh, if we talk about this part of something then people won’t focus on the actual part of substance. You could go with that kind of theory or you could go with the theory of Oh, they just got Roseanne out, this other woman said something, so we should do a tit for tat here. People just don’t like that word, I guess! I was like “feckless,” eh? That’s a real Thesaurus word for you! [Laughs]

You know Trump had to look that one up. It was probably like that scene in Analyze This with the mobster: “Get a dictionary and find out what this ‘feckless’ is. If that’s what she’s going to hit us with, I want to know what it is.”

There’s no way! There are so many people in that administration that had to be like, I’m sorry, “feckless?” There’s no way Jesse Watters was like, “I’m aware of that word!” Or Steve Doocy. [Laughs] I really think that if you couch something in a joke, you can say whatever you want. I’m guessing the reason she had to apologize was because sponsors were pulling out.

And the way the words “feckless cunt” were removed from the context of the joke seemed to be problematic.

Right. I would guess that most people don’t even know what joke that was in. They probably just saw the headline: “Samantha Bee calls Ivanka Trump a feckless cunt.” They don’t know it was a bit about ICE, and they may not even know that Ivanka posted that picture or really so much about that. I mean, Ivanka is part of the Trump administration. She’s fair game. And she is useless. So I think it’s very fair to point out that she’s doing a terrible job.

And that’s why you shouldn’t underestimate women: They’ll look like a pretty little girl and they’ll steal the children right out from under you.
Michelle Wolf on Ivanka Trump

She was also a big reason her father got elected president.

Yeah. Aw, she’s one of those worst kind of girls. We’re all fooled by her because Eric and Don Jr. aren’t attractive, and then we pull that, Well, she’s just a little girl! She’s just a pretty little girl. And that’s why you shouldn’t underestimate women: they’ll look like a pretty little girl and they’ll steal the children right out from under you.

I really enjoyed the first two episodes of The Break. I’m curious how you feel it differentiates itself from other talk shows. For me, the thing that really sets it apart is that its spirit is rooted in stand-up.

Yeah, I wanted to play to my strengths, and I guess the normal convention of monologue jokes I wanted to get away from—that standard setup-punchline. Even when I was writing them for other people I thought there was more to explore, and I wanted to take it more from a stand-up approach where it felt like a bit, and the news peg felt like a jumping-off point rather than the entire premise.

The Break also tackles different subjects. While I enjoy much of the late-night comedy out there, there is a lot of repetition—comedians riffing on the same two or three big stories in the news.

We make a conscious effort to do that—and also, we have to be conscious of the fact that we tape on Thursdays and it airs on Sunday, and we want to make sure that the things we’re doing jokes on have the best chance of still being around. So much of this other news moves so quickly, so even if we wanted to do it—which we don’t—it would feel stale by the time we got to it.

Right. You must be used to reacting quickly to the news from your days on Late Night and The Daily Show. What’s it like to write for a weekly program now? Does it give you anxiety, knowing how quickly the news cycle moves? 

It’s weird because I thought it would be less stressful since you don’t have a show every day, but I feel like there’s more pressure on every part of the show because it is only once a week. I walked in thinking that if you do a once-a-week show, every joke should be a home run—there should be no reason that something falls flat. There’s an odd amount of pressure to really nail it, which I enjoy, but it puts more weight on each individual show since they’re further apart.

How did you land on the current format? Were there others you workshopped that didn’t feel right?

We’re still developing it, to be honest. Like any show, I feel it’s going to change and evolve as we grow and find out what works best. We have segments that we haven’t even tried out yet. We just really need to see what our strengths are. I definitely think the monologue is my favorite thing—mostly because it’s stand-up—and I don’t anticipate that changing at all, but with everything else we’re just throwing stuff out there that we really like and seeing what feels right for the show, and for the tone. Hopefully we get the opportunity to keep cultivating it and making it what we want it to be. The great thing about being on something like Netflix is there’s no rules or time constraints, so we have the freedom to really experiment and want to take full advantage of that—including doing some things that you wouldn’t be able to on network TV.

You’re not beholden to advertisers either, which is a nice freedom—and something that I imagine posed a bit of a problem for the shows you’ve worked on in the past.

Oh, yeah. There were so many times where you’d write a monologue and the punchline would be some specific car type, and they’d come back and be like, “We can’t make fun of this car company, they’re a sponsor.” And if we upset a whole bunch of people, it’s not like a bunch of sponsors can pull out. [Laughs] So it allows you to take bigger swings.

There really aren’t too many women in late night—there’s you, Samantha Bee and Robin Thede—and in the Trump era, it seems more necessary than ever to highlight the female perspective on issues like #MeToo, reproductive rights, etc.

I always felt on the other shows I worked on that there were jokes that I would want to do that wouldn’t sound right coming out of the men I worked for’s mouths, so I’ve always felt a need for it. It’s sort of silly—we’re over half the population. And our points of view are slightly different because we have different experiences in life, so that’s why it’s incredibly important to have people of different backgrounds hosting things because you’ll relate to those people differently. There are a lot of men in late night where, their wife will have a baby and they’ll tell a story about it, and it’s always very cute and lovely but my first thought is, “It just happened yesterday and you’re back at work!” That would be a very different story if the host were female.

This reminds me of your great #MeToo set on The Daily Show—“pull out your dick, get replaced by a chick.” Men are just ill-equipped when it comes to weighing in on these issues, and I think that’s why the men of late night have struggled mightily when it comes to tackling Weinstein and #MeToo.

It’s all in the movement of how we need people who can speak for women, and people who know about women’s experiences—not that all women have the same experiences, since we all have different experiences, but there’s just a certain understanding.

You’ve worked in several writers’ rooms but now you’re in charge of one. What’s that like? And what did you take away from your experience working in them on Late Night and The Daily Show?

I think it’s really important that everyone feels comfortable—that they can say and pitch whatever they want. Even if they think it’s a terrible idea, someone may find something funny in it, so it’s important to have an environment where everything is OK. Also, I’ve written for people for a long time and was interested in seeing what it would be like to have people write for me, and I’ve been so pleasantly surprised—and I think this is only because we have such amazing writers—that they’ve done such a great job writing jokes. I tried to build a room where there are people that think different than me and also that have strengths that I think are my weaknesses. So I got a lot of good sketch writers, because I don’t think I’m as strong of a sketch writer, and people that have different perspectives. I don’t want a bunch of people that think like me. I think like me.

You’re pretty seasoned when it comes to stand-up, but what about sketch-comedy acting and interviewing people on the couch? How’s it been flexing those new muscles?

With the sketches, I don’t know. [Laughs] I don’t know if I’m a good or terrible actor, but we’re having fun making them and I think so far they’re going OK. I just try to have fun with it, I guess! I guess I’m faking it and trying to pretend I’m a good actor. And instead of doing the traditional interviews with guests we do bits with them that are written, for the most part. I really wanted to have it so that the guest didn’t have to come on the show with their own story, and that we could just do a bit together that allowed us both to be funny, and that they didn’t find it to be too much work since we provide them with a good amount of jokes.

I’ve thought about how difficult it must be for comedians to do late-night guest spots, because you’re essentially wasting a bit. As much as I loved John Mulaney’s recent stand-up special, I remember seeing his Trump-is-a-horse-loose-in-a-hospital bit on Colbert previously. 

You’re burning a bit—and you don’t necessarily want to! If you’ve got a good bit, you want to save it from your album, or your special, or even if you’re doing stand-up on late-night, because the rhythm of doing it on the couch is kind of off. We’re not having a guest on every show either—we’re kind of playing with that format too—but I wanted most of the guests to be comedians, and people I like and know I have fun with, rather than being like, oh, this person has a movie coming out.

What’s it like just navigating the world of comedy these days? It seems to be pretty treacherous terrain, especially when you have a presidential administration demanding that certain comedians be reprimanded (in your case) or fired (in the case of Samantha Bee) should certain jokes be misconstrued or perhaps go too far.

I always think of it as: it’s my responsibility to write the jokes and say the jokes. How they’re interpreted—and all that aftermath—is completely out of my control. I can have said something with the very best intentions and people can take it completely out of context. I have no control over that, so all I can do is try to write the funniest joke possible that’s true to who I am and my point of view.

The one thing people need to be very careful of is, if you’re watching a comedian at a club or a show, you don’t know how new that material is for them so you can’t judge them off of that because they’re probably still working on that joke. That’s what really bothers me, is when someone reports on something that happened inside a club and I’m like, but that joke’s not done yet! You’ve gotta wait till they publish it. It’s like stealing a script from a screenwriter and giving away a scene before it’s put into a movie—you don’t know what that end product is actually going to be. And especially right now, there are so many topics that are hard to write jokes on, and it sometimes takes you a really long time to get a punchline that works. You’ve gotta let people have that time to experiment and see what works and see what falls flat.

Back to the White House Correspondents’ Dinner. I enjoyed your closing bit taking the media to task over their Trump coverage. There was a great piece in The Atlantic recently called “Just Say It’s Racist,” about the media’s “ludicrous and expanding menu of complex euphemisms for describing racist behavior” under Trump. That also seems to apply to the word “lie,” with reporters doing these bizarre linguistic gymnastics instead of just calling a Trump lie for what it is.

I don’t know if it’s just them being pussies and not wanting to use actual words, or if they all just got a Thesaurus for Christmas and are trying to expand their vocabulary, but I think in general their journalism has been very irresponsible. It certainly hasn’t served the people and it definitely has served Trump.