Knock 'Em Dead

Nikki Glaser Would Be Disappointed in Herself Too, If She Weren’t So Damn Funny

After roasting Tom Brady to a crisp live on Netflix, Glaser has a brand-new comedy special, Someday You’ll Die, hitting HBO May 11.
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Jennifer Rose Clasen

Nikki Glaser didn’t fully appreciate how expertly she roasted Tom Brady while it was actually happening. “I didn’t know how big it was until it was over because, obviously, it was live,” she tells VF. And then she checked her phone. “Text messages were rolling in like someone in my life had died.”

While no one did, Glaser absolutely killed her set on Sunday, May 2, during The Roast of Tom Brady, a.k.a. The Greatest Roast of All Time, Netflix’s live roast of seven-time Super Bowl champion Tom Brady. In a lineup that included comic greats like Kevin Hart and Will Ferrell; NFL royalty like Brady, Peyton Manning, and Bill Belichick; and mega-celebrities like Kim Kardashian and Ben Affleck, it was Glaser who walked away as the winner of the night.

Her jokes were as brutal as they were true. “Tom Brady: five-time Super Bowl MVP, most career wins, most career touchdowns, you have seven rings–well, eight now that Gisele gave hers back,” Glaser said. “You’re the best to ever play for too long. I mean, you retired, then you came back, and then you retired again. I get it. It’s hard to walk away from something that’s not your pregnant girlfriend,” she said, in a nod to how Brady’s relationship with Bridget Moynahan ended. She had so much Brady material that innocent bystanders like Rob Gronkowski started getting hit as well. “Tom also lost $30 million in crypto. Tom, how did you fall for that? Even Gronk was like, ‘Me know that not real money!’”

ADAM ROSE/Netflix.

“I knew it would be a big deal, but it feels good, because I worked really, really hard,” Glaser says. “It felt like, Okay, I did an A-plus. Like I got back my test and it’s hanging on the refrigerator for a couple days.”

Of course, there are those who would like to give Glaser an F. Days after the roast, a source told People that supermodel Gisele Bündchen, Brady’s ex-wife and mother to their two children, was “deeply disappointed” by the “disrespectful” jokes made at her and her family’s expense. “I mean, I would be disappointed in me if I were Giselle as well,” Glaser says. She then walks me through the rationale behind her Bündchen material—how she tried to soften the blows thrown at the model, who, unlike her ex-husband, did not sign up to be made fun of in front of the entire world. “Even saying her name, I tried to maybe say it less than I needed to,” she notes. “In my final joke about her, I said, ‘ex-wife.’ I tried not to mention her name as much as possible, but he’s a part of her story.… That’s how I rationalize talking about someone who did not ask to be part of this conversation.”

At the end of the day, Glaser stands by her material. “The worst thing I said about her was that she gets her ass eaten by her new boyfriend,” Glaser says, referencing Bündchen’s boyfriend, jiujitsu instructor Joaquim Valente. “I think that even though that’s probably a visual that she would want out there, it’s a joke. It’s not like I’m saying I witnessed it, or it happened. Also, that’s a really nice thing to wish for someone in their private life. I think that would feel pretty good, actually.”

As a veteran comic, Glaser knows firsthand that feelings inevitably get hurt during the ritual of a roast. “There were only a couple of jokes about me, but they hurt, and they’ve lingered, and I’ve focused on them a little too much,” she admits. What were the jokes that stung the most? “There was one that said I looked like Tiffany Trump. There were a lot that said I had an eating disorder,” she says. “There’s a lot of that processing and being like, Why was that joke written? The weird part is, you think it won’t hurt you, and every time it does. You’re sitting there smiling and laughing, and I’m just turning off my brain in the moment because I don’t want any offense to register. But then I subconsciously store it away for later and torture myself over it.”

Glaser knows that’s the roaster’s paradox. “It’s the risk you take,” she says. “That’s what this is. You have to dish it out, you have to take it.”

Glaser certainly proved she can dish it out, ripping Tom Brady a new one without ever having met the man. “My first time meeting him was when I was up on the podium,” she says. “That’s the first time I’ve ever talked to him. We didn’t meet backstage. We didn’t have a Zoom call. There was no preface to this. Which made it easier to go hard.”

Now it’s safe to say Brady knows who she is. “Tom Brady knows my name now,” she says in disbelief. “In his joke, he didn’t say it fully, but he said ‘Glaser.’ He said it right.” It’s clear that Glaser is still processing her whirlwind week. “I will never get this much attention until I die,” she says. “I have an inkling of what it feels like to be Taylor Swift on a really slow day for her.”

But being Taylor Swift on a slow day is still life-changing for Glaser, who has been a professional comedian for more than 20 years. “I ascended in my career more than I ever have, overnight,” she says. “It just doesn’t happen today with how oversaturated the content is—that all eyes are on something like this.” She adds a joke for good measure. “Outside of Will Smith slapping me, I don’t think I’ll get this much attention as a comedian in my life.”

Matt Winkelmeyer/Netflix.

Glaser’s timing couldn’t be better. Her next comedy special, Someday You’ll Die, drops on HBO this Saturday, May 11. In the special, the 39-year-old comedian loudly and proudly declares that she never wants to have kids, expressing her raw, unfiltered emotions about aging and motherhood the only way she knows how. “My truth is that I don’t have kids, and I really do get jealous when my friends have babies because I don’t see them anymore,” she tells VF. “The funniest take on that for me is when my friends are trying, I’m like, Please don’t let this one take. It’s a funny thing to admit because it’s insane, but I can’t help that it did enter my brain. Like, Oh, I want her to have a kid. Just not yet, because we have a girl’s trip coming up.”

That’s not to say Someday You’ll Die is only about one thing. In the special, Glaser wisecracks about topics included but not limited to abortion, suicide, autism, gang bangs, heroin, and, yes, there’s even a non-terrible trans joke or two. In an age where stalwart comedians like Jerry Seinfeld continually lament so-called PC culture and what they see as the corresponding death of comedy, Glaser is proof that you can still say basically anything you want, as long as it’s funny.

“It’s funny that Jerry says that because he’s a clean comedian,” she says. “Who is he offending? I don’t know. He’s mastered the art of being clean, and is as funny as any comic who’s dirty.” Glaser says that she longs to have the type of clean and accessible comedy act that is de rigueur for Seinfeld, but it’s just not in the cards for her. “I can be very filthy and I can be very dark, so I sense that I turn people off a lot,” she says. “But I know at my core, I’m a good person. So if I’m joking about stuff, it’s just because it’s true and I want to draw attention to it.”

“It’s not about wanting to hurt people’s feelings,” she adds. “I want everyone to see what’s going on. Let’s talk about slaves making our clothes. Open your eyes. Making a joke about them is not going to make them any more slaves than they are. It actually might draw more awareness to it, even though it is under the guise of a joke. At least just acknowledge that slaves made your clothes by laughing at this joke, because it is happening and you know it.”

The intersection of truth and comedy has long been a hot-button issue, particularly as comics like Hasan Minhaj come under fire for embellishing or fabricating stories they tell in their stand-up. Glaser isn’t interested in storytelling comedians—“I just do not have the patience for it”—but she is interested in truth, even if it’s at times unflattering. “I’m never really lying on stage,” Glaser says. “People can go, ‘Oh, she’s just hyperbolizing for the sake of comedy.’ But I’m not really. Yes, I do turn it up a notch, but it should be obvious, the things in the story I’m lying about. To a savvy consumer of stand-up comedy, you should be able to tell where I’m doing a punch line and then where there is actual storytelling happening.”

“I like to just start from a place of what’s true, because that’s, I think, where the funniest stuff is,” she says. “What’s the truest thing that’s not being said?

And sometimes she can be a little too truthful in her comedy. “I had a joke about how if you’re with a group of people, if you have to go to the bathroom and it’s number two, you go fast so people think it’s a number one. You try to go as fast as you can,” she says, gaining momentum. “And sometimes it’s one that’s a little bit more chaotic than other number twos, but you have to clean it up really fast and just get back out there and get back to your table.” She pauses to fill me in on the inspiration for this graphic bit of potty humor. “This was something that was written on stage, because it had just happened to me. You’re like, Oh my God. You’re smelling the air, because you’re like, Did I not get it all? Is some of it still on my wrist? And I said, ‘Wrist.’ And the crowd laughed so hard, and I was like, Thank you, God.

Jennifer Rose Clasen