Stand-Up Star Nikki Glaser Tells Howard Her Unaired Jokes From the Roast of Tom Brady

Entertainer also opens up to Howard about spending big bucks on Taylor Swift tickets and how comedy may have saved her life

May 6, 2024

The closest thing stand-up comedy has to a Super Bowl may be a star-studded celebrity roast, as seen on Sunday night when many of the funniest comics in the business competed for laughs while goofing on N.F.L. legend Tom Brady in what has been dubbed “the Greatest Roast of All Time.” No one on the dais was spared as A-list comics and athletes alike sent digs in every direction and, while no official winner was crowned, critics and even guest host Kevin Hart agreed that superstar stand-up Nikki Glaser delivered one of the night’s most unforgettable sets.

So, what did Nikki do after crushing it in the Super Bowl of comedy? The 39-year-old comedian, podcaster, and actress didn’t go to Disney World — she returned to the Stern Show, sitting down with Howard for a riveting conversation covering everything from her long-term boyfriend and how comedy helped her through some of her toughest times to why she spent over $25,000 following Taylor Swift around on her recent tour. Howard and Nikki also discussed the Tom Brady roast, of course, with Nikki revealing who was funnier than she realized, which jokes she couldn’t tell on TV, and why receiving a standing ovation meant so much to her.

Photo: Getty Images for SiriusXM

“It’s the biggest crowd I’ve ever performed for. It’s live on Netflix. It’s doing a set I’ve never done in this context,” Nikki told Howard of Sunday night’s performance. “It’s a high risk situation, and I was terrified going into it.”

“You were killing it,” Howard responded before playing clips of a few highlights from the night, including several of Nikki’s funniest barbs and the kind words Hart had for the audience after her set.

Nikki thanked Kevin for being so nice. “I’ll love him forever,” she told Howard of Hart.

The roast was of course more frequently savage than sweet. From Tom Brady’s breakups to his murderous ex-teammates, almost every topic was fair game. However, Nikki and her co-stars did largely steer clear of one subject: “We all collectively decided not to involve his kids too much in anything because they didn’t ask for that,” she told Howard. “So, I couldn’t say, ‘Tom, hopefully we make out at the after party — you can pretend I’m your son.’”

“Were there jokes you left out of your set?” Howard wondered.

“So many,” Nikki responded, explaining that some jokes didn’t hit hard enough while others were cut for time. Thankfully for Stern Show listeners, she debuted some of the cut jokes on the air with Howard on Monday morning.

“Thank you all for being here tonight and taking some time away from cheating on your wives,” Nikki began. “It’s not their fault, it’s their wives’ fault for aging naturally.”

“These guys really fucking damage their bodies and their brains all for the sake of guys hugging each other at a Buffalo Wild Wings,” Glaser continued. “Like, I hope it was worth it fellas.”

The Joke Tom Brady Thought Went Too Far

Tom Brady had dozens of insults hurled his way during Sunday night’s roast and took most of them in stride, but the iconic quarterback did seem to get upset after comedian Jeff Ross set his sights on New England Patriots owner Robert Kraft. The joke in question, which alluded to Kraft’s massage parlor-based legal issues in 2019, led to Brady getting up from his seat and telling Ross to “never say that shit again.” It was one of the most shocking moments of the evening, and Howard wondered if it was real.

“I believe that was for real,” Nikki responded. “Based on the little knowledge I had of [the roast], I think Robert Kraft was not a confirmed guest to be there.”

“I was surprised when Jeff made that joke, but I do think that Tom was actually looking out for him,” she continued, adding that after Jeff’s set the comedian seemed “a little bit worried” he might’ve crossed the line.

“We have consciences about these things, you know? Afterwards we go, ‘Did that really hurt his feelings?’” Nikki concluded. “[Tom] had to do it performatively for Robert … but I’m sure it’s not an issue Jeff is gonna hear about today.”

How Stand-Up Comedy Saved Her Life

Though Nikki was able to quit drinking with the help of a book, she had to rely on a 12-step program to deal with a separate issue — the eating disorder she developed when she was just a teenager. When the young Glaser was once too nervous to eat because she was going on a date with a crush of hers, a fellow classmate paid her a compliment. “The next day this girl … was like, ‘Nikki, you look amazing,’” she said before recalling how things soon spun out of control. “And then we graduated, and I was hospitalized … I really wanted to die, and I was going to.”

Fortunately, when a college friend signed her up to perform on a campus comedy show, Nikki found a beacon of hope. “I called my dad, and I was like, ‘I know what I want to do — I found it,’” the comedian remembered. “The next day I called the counseling service at CU Boulder, and I said, ‘I have an eating disorder and I want to get help for it.’”

Glaser continued. “I was like, ‘Okay, I’ve got to beat this because now I have something I actually want to do and I’m good at — something to live for.’”

Still, Nikki wasn’t sure exactly what to do for that first show — so she looked it up. “I typed in ‘stand-up comedy woman’ and Sarah Silverman pops up,” she noted. “I loved comedy but not in a way that I saw an ‘in’ … and then when I saw Sarah Silverman it was just like, ‘Okay, that’s it — that’s what I’m going to do.’”

When Glaser speaks to young comics, she advises them to do what she did — pretend they’re writing for their favorite comic. “I just wrote jokes like I was writing for Sarah, and I definitely had a knack for writing one-liner jokes,” the roast veteran explained.

Nikki’s Relationship With Her Boyfriend

Sober for over a decade, Nikki said she was dependent on alcohol for much of her 20s as a coping tool, especially with relationships. “I think it really helped with nerves … but it mostly helped with sex,” she confessed to Howard. “I’ve always had this fear of I’m going to be bad at this … and then it just took that away.”

Upon quitting drinking, it would be two years before the comedian had sex again. “I went from like hooking up pretty frequently to not kissing anyone, not doing anything,” she recalled. “I’m still with the first person that I hooked up with after I quit drinking because I really had to get to know him and really like him and crave him sexually in a way that wasn’t just brought on by being drunk.”

The relationship, with producer Chris Convy, has been off and on for a decade — something she addresses in her latest special, “Nikki Glaser: Someday You’ll Die,” which premieres May 11 on HBO. “Forever makes me think of no other adventures, it’s just kind of admitting defeat,” Nikki explained to Howard of her own commitment issues.

Another difficult aspect of their relationship in the past, as Glaser admitted, was that she wasn’t always honest with her partner. “I thought getting a boyfriend meant just like being agreeable,” she said. “I never, ever complained about anything … and then I’d air those complaints on podcasts … he eventually heard them and [went], ‘I don’t recognize who this person is.’”

These days, the couple is in a much better place. “He really got me to stop lying,” the comedian noted. “I’m not perfect at it because I still fear abandonment, so there are some issues in our relationship where … I’ll just give the answer that I think he wants.”

Nikki Spent Over $25,000 Following Taylor Swift on Tour

As a Taylor Swift superfan, Nikki was dismayed when a soundbite of her critiquing Taylor’s appearance made its way into the 2020 documentary “Taylor Swift: Miss Americana.” “I was mouthing off on some interview about her in a way that was not kind, but it was me being jealous and feeling like I couldn’t be friends with her,” Nikki told Howard. “Then it comes out in the documentary that she was anorexic. I was like, ‘What the fuck?’”

“I was commenting on somebody’s body who has the same fucking thing I did. It was so grotesque, so I issued an apology on Instagram,” Glaser continued, adding, “She wrote back to me in the comments — like, ‘Thank you so much. This means so much to me.’”

Nikki’s love for Taylor has only grown since then. She told Howard she spent over $25,000 following her around on her last tour. The decision was made after she realized she no longer wanted to freeze her eggs, which would’ve cost a lot of money. “I was [considering] freezing my eggs in case I break up with my boyfriend — who I don’t plan on breaking up with — and I meet a guy who refuses to adopt … and then I felt sad about it, so I said, ‘I’m not doing this’ … and that’s when the tour was announced,” Nikki told Howard.

It was the boyfriend who encouraged Nikki to indulge her inner-Swiftie. “He said … ‘Who knows when she will [go on tour] again? It’s the thing that brings you the most joy … Taylor Swift is your life … Go to every chance you have.’ So, I did,” Glaser recalled, adding, “I was on [my comedy] tour last year … I did at least like 60 different cities, and I also went to 12 different cities for Taylor Swift. I went on like two tours.”

Speaking of boyfriends, Howard wondered how Nikki felt about Taylor’s relationship with football star Travis Kelce.

“It’s so hard for something with that much attention to last, but I hope it lasts forever, and I really like him for her,” Nikki concluded.

“The Roast of Tom Brady” is available now on Netflix. “Nikki Glaser: Someday You’ll Die” premieres May 11 on HBO.

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