Nikki Glaser on the One Ann Coulter Roast Joke She Regrets

Nikki Glaser was telling an extremely dirty joke during the taping for her most recent Netflix special Bangin’ when she spotted her father in the crowd.

“I was in the middle of my set talking about guzzling cum or just something filthy and I see my dad’s head in the audience,” Glaser tells me on this week’s episode of The Last Laugh podcast. “And my dad and mom have seen everything I do, they know what I talk about, I don’t hold back at all. And it was the first time that I was like, that would be really hard to hear if you were a parent. He probably doesn’t want to hear this at all!”

If this self-described lack of “empathy” has occasionally complicated her personal life, it has been a major asset for Nikki Glaser’s side hustle as one of the best celebrity roasters of all-time. She first broke through by taking Ann Coulter to the mat at the Comedy Central Roast of Rob Lowe in 2016 before following that up with even tougher jokes at the subsequent roasts of Bruce Willis and Alec Baldwin.

“It’s allowed me to be so brazen on stage and say things that most people wouldn’t,” she says of the emotional “superpower” that has turned her into a comedy superstar. “Because I’m not thinking about how people will react.”

Below is an edited excerpt from our conversation and you can listen to the whole thing—including why she wanted to host FBoy Island, and what to expect from her next hour-long special—right now by subscribing to The Last Laugh on Apple Podcasts, Spotify, Google, Stitcher, Amazon Music, or wherever you get your podcasts and be the first to hear new episodes when they are released every Tuesday.

The first [roast] you did was the Rob Lowe roast in 2016 and I remember it mostly for Ann Coulter’s horrible bomb. Looking back at it, you really went at her I think harder than anyone else on that stage.

I remember Amy Schumer was really in my corner for that set and she was someone that I had helped with jokes before. And so she really was like, this is a huge opportunity to tell this woman what we all want to tell her. She’s truly evil. And so I just went to a place of, like, I really want to go as hard on her as possible. Because for the first time at a roast, she really deserves it. We roasted Donald Trump before, but we didn’t know how much we all would hate him. There’s rarely been someone there that is that loathed and deserving of being loathed and knows what they’re doing and has made a character that is evil on purpose because they’re a sad person inside.

It was my first roast, so I made some choices that I didn’t like. The joke that honestly broke my career open—I don’t regret it, I guess, but I kind of do—was the one that was like, “The only person you’ll ever make happy is the Mexican who digs your grave.” I didn’t like that I said “Mexican.” I look back on that joke and that’s making me someone who assumes that Mexicans dig graves, which I guess is a stereotypical thing that you could put in a joke. But everyone loved that joke and was like, “That’s so mean to her!” And I feel like that joke is more mean to Mexicans for no fucking reason, saying that that’s all they do. And that it’s a foregone conclusion that it’s going to be a Mexican and obviously Mexicans hate you because of your immigration beliefs. That joke is always quoted back to me. And I cringe when I hear it, because if I were Mexican, I would have been like, “This fucking bitch, we don’t need her to speak for us.” It’s a great joke and it wasn’t written by me and I took it on right before I went on stage. I added it to my set because why not? But I already had that kind of spidey-sense of, like, this doesn’t feel good.

It was also the first time that I had experienced this thing where I write all these mean jokes and then I get there and I forget that they are going to be sitting there when I say it. I literally forget. And I remember being on the red carpet before that and getting asked, “So how do you feel about saying these jokes to these people?” And I was like, oh my god, I had not even thought of it. And you know what, that’s my superpower, is this inability to think about the scariest thing until it’s about to happen and it’s too late.

I wonder if that helps explain why you’re so good at the roasts.

I think it does. It’s like the fear of heights that that Free Solo guy has. I just don’t have it when it comes to offending people. But also when I find out I’ve offended people, Matt, I am so upset and want to find them and right the wrong. I don’t enjoy offending people. People think I love making people feel awkward. And I hate it! So the Rob Lowe roast was the night that I got to prove myself to Comedy Central. And I feel really confident about what I did and I worked my fucking ass off. And I was a little hurt by the jokes that they said about me. And I didn’t expect that, but just as I don’t have empathy for the person on the other side of my jokes, I did not prepare myself at all for what would be said about me.

You weren’t thinking about that?

No! And thank god, because I guess it was better in the moment. But I don’t know, I usually get wildly depressed after these because I’m like, “I have to get injections in my face so they won’t say that next time?” And then they’ll make fun of you having injections in your face, so you can’t win.

Yeah, I talked to Natasha Leggero about how there’s only a handful of ways that people roast female comedians.

Old, slut, not funny. That’s it.

And you kind of move from “slut” to “old” as the years go on.

Yeah! And “old slut” becomes like, gross, no one wants you, how pathetic is that? And it’s funny, at these roasts, I go first all the time. So any jokes about me not being funny just don’t work because I just killed. And I love that. There was one time where someone really impressive was up there and I was like, I can’t wait for them to even just say my name. And I remember I just so undoubtedly killed that there was a joke on the teleprompter that was about me not being funny and they just go, “Actually, just skip that one.” So I tend to hear jokes about me looking like a male to female transsexual, or me looking old, or me having no ass, or me having a horse face. I mean, these are all things you say about skinny women. Or having an eating disorder, which you know, is true—or was true—but like, who cares? But they do find new ways to like really hurt my feelings, which, you know, is the goal.

So the next one was Bruce Willis in 2018. Is there anything that stands out from that one?

That one was so fun because I got to sit next to Edward Norton, who I was a big fan of, very intimidated by. And he didn’t really have much to say to me before the show. He was kind enough, but we weren’t chit-chatting. And I was like, I guess we’re not going to be buds or whatever. Because he was probably nervous. I was too. Not rude at all, but I wanted to have a connection with this guy. But then I go up and I do my set and then I come back and now Edward is a fan, because he just saw me work and respects me more and is much more chatty and all of a sudden we’re friends. And it was like, yes! So then after his set, I split an edible with him. And he was telling me hilarious stories about Bruce from when they worked together and I had a real night with Edward Norton. I got Edward Norton alone and was able to be friendly with him and social in a setting that I don’t think anyone else could ever get a person of that caliber, coming in as a stranger in that situation.

Did you stay friends?

No, you know, I was hoping that he would slide [into my DMs] or find a way to get in touch with me so that we could remain friends. But no. But I do know that if I ran into him again, he would remember me because it was a mutual admiration. It felt so good to be able to perform. Because when I meet someone who’s super famous, who I love, I know that they would love me, but they’re not aware of me. And I want them so badly to see me perform so that they can have respect for what I do.

And then there was Alec Baldwin.

My memory from the Alec Baldwin roast was just being devastated afterwards, because I forgot to do two jokes. Well, actually, two jokes had been cut the morning of because Caitlyn Jenner found out that someone had been practicing a set around town talking about her car crash. And she did not want jokes about that.

There were no jokes at all about it in the whole roast, huh?

No jokes at all. And there were some really good ones. And unless I’m told specifically not to do something, I’m going to do it. And Comedy Central was like, we strongly suggest you don’t. And I go, “But have you heard that from her? Can I talk to her and ask her?” And they wouldn’t let me talk to her. So the morning of the roast, they finally go, “Listen, she heard that someone might be doing jokes about it and she said she would walk off the stage if that happened.” And I was like, OK, then I’ll pull them. Like I said, I don’t want to make anyone uncomfortable.

Then there was another joke that I loved so much. It was, “Alec Baldwin has a podcast called Here’s the Thing, which is exactly how he introduced Caitlyn to me backstage.” Which I thought was just a beautiful joke. And I fucking forgot to do it. It just didn’t end up in the script. And then I’m on stage and I heard someone reference his podcast, and I go, “[Gasps] Can I get up and do it again?” I was freaking out. And then afterwards, I cried at the after party. I had the set of my life. That was the set that blew me up and changed my life. And I was devastated. I couldn’t have any fun. And that was one of the last times I let a regret during a live performance send me into a tailspin.

But the one thing that I do remember the most and a decision that I stand by is when I assembled my writing team for that, I always give a kind of mission statement for each person. And for Blake Griffin, I was like, I just want every joke to be about how hot he is and how I want to fuck him. And my writers were like, but it’s a roast. And I’m like, find a way to make it work. Because the thing is, I’m really bad at letting boys know I like them. I’m so brazen on stage, but I’m not good at being like, “I like you and would entertain going on a date with you.” I would rather make jokes about it so that I can get off on the fact that if he doesn’t want me, I can be like, “Oh, they’re just jokes.” But if he does, I just like gave you the in, now you know.

So did he take the in?

Well, it was funny because we definitely had a nice time talking before and we were sitting right next to each other, randomly enough… because I asked to be placed next to him at rehearsal. Because I knew from the Edward Norton thing that whoever you’re sitting next to, you really talk to all night. So we definitely were having a flirtation. And my whole set was about wanting to fuck him. And then he got up on stage and said I looked like Larry Bird and that I couldn’t pass for 33, because he was number 33. And he said a couple other things that were so mean. And I know who wrote those jokes for him. And that’s not blowing his cover. Blake is hilarious, legit hilarious.

Everybody gets other comedians to write jokes for them.

Yeah, I probably wrote as many jokes in my set as Blake wrote in his. There’s no shame in having other people write jokes for you and Blake truly is a funny person. But I think Jimmy Carr wrote some of those jokes and Jimmy is always a person that whenever I’m in a setting where he can poke fun at me, he can be so mean. He’s just too acute with his insults and they can be so mean about my looks, which I do not handle well, because that stems from all of my insecurities about feeling that I’m somehow ugly. So when I found out, I was like, “Jimmy fucking Carr!”

And I think maybe Neal Brennan wrote some too. And Neal is very insecure about his looks so he’s able to write to that as well. He’s able to really nail it. And so when I found that out, I was like, fuck those guys. But at the time I was more like, fuck Blake. Which was a good feeling, because if a boy is mean to you, in the past I’d be like, I like him more. But this made me like, ugh. If you are able to say those things about me, I don’t want my husband—and I know that, like, our arms just touched, but I was already marrying him in my head—I can’t marry someone who said I looked like Larry Bird, this is over! And then he did slide into my DMs eventually. He DM’ed me, like, “The people have spoken, I think we have to give them what they want.” And I was like, “Yeah, I’m down” And then we were going to hang out if he ever came to New York. And I guess he just hasn’t come to New York at all, even though I think he definitely is there? So no, we have not connected since. But I got the slide in my DMs and that’s probably all I really want in the end anyway. Because I’m scared of intimacy.

The other joke that did stand out to me rewatching it is the one you made about Jeff Ross, when you asked him, “How do you get 10s, I mean teens?” That’s a joke that has aged kind of complicatedly, I would say.

Yeah, unlike the women he dates. No, I’m just kidding. I’m friends with Jeff Ross and feel very conflicted about all of that. And that joke was actually used in—someone wrote something about the allegations against him and referenced that joke as like, “She knew!” And I’m like, no, I know that his girlfriends are like decades younger than him, but that’s the same for every male comedian in their forties or fifties, or whatever Jeff is.

So it wasn’t exposing some open secret?

No, it was me making a joke of how he dates young hot girls, but not like illegal hot girls. And you can’t take roast jokes as facts. Although, I am trying to call out things that maybe people wouldn’t know about other people. And I guess someone could say, like, ”Oh my god, she knew about the accusations that would come up!” But I didn’t and it was not from that place, it was just a coincidence. And I hate even talking about any of this stuff, as you can tell, I’m tensing up. I was talking about the Aziz [Ansari] thing recently on a podcast and I was just like, can we just move on? Because I honestly see both sides of it and I never don’t want to trust women. And I also know that—and this isn’t about Aziz or about Jeff or about anyone—but I truly believe that I could be friends with a lot of monsters. I think there are a lot of people out there that have done disgusting things—both women and men that have done disgusting things—and my whole policy now is, I don’t care if you keep working.

Louis C.K. Has No Choice But to Handle Allegations NowFINALLY

Matt Wilstein, Melissa Leon

Bill Cosby, go on tour! I don’t want him to. I wish I could literally kill him with my bare hands. He’s the only person that I would probably want to murder, just because I’ve seen his show, actually. I’ve hated Bill Cosby since he came to my college in 2006. I fell asleep during his show. I’ve always hated Bill Cosby. I didn’t know that he was going to be one of the most prolific serial rapists we’ve ever known—allegedly—but I just feel like it’s up to the consumer. I was on board with “cancel culture” for a while and now I’m just really scared of it. And I think that everyone just needs to make up their mind whether they want to consume it or not. I am just trying my best to love everyone and hear everyone out and give everyone the benefit of the doubt before I try to cancel or pile on. But sometimes it’s tempting because sometimes you already hate someone comedically and then they come out as a pedophile and you go, I’ve always resented your success because you’re not even funny. And now you’re a creep, fuck yes! And then for some comedians like Louis [C.K.], I can’t watch him anymore. It’s not that I wouldn’t enjoy him. I probably would love his new stuff, but I’ve heard he doesn’t talk about the thing.

Yeah, I feel like if he did an hour about that—

I would be back on board!

I think it would make a huge difference. And that’s why I don’t know why he doesn’t do it because I think it would give him some credit.

I’m sure he has his reasons. But it’s a personal choice for me. I don’t understand why my brain works this way. I can still enjoy Michael Jackson. I can still enjoy some Chris Brown songs that aren’t about loving and cherishing women. Because for me to enjoy those songs, I need to believe the person singing them loves and cherishes women. So what he’s done goes against that. For me to enjoy Thriller, I don’t need to think that [Michael Jackson] hasn’t molested children. For Louis, to enjoy him, I need to trust him.

Next week on The Last Laugh podcast: Comedian and star of Bob’s Burgers and The Mysterious Benedict Society, Kristen Schaal.