Adam Sandler details bizarre heckle from 'devastatingly bad' early stand-up gig in exclusive My N...

&34;It was five minutes of just silence,&34; the &34;Happy Gilmore&34; star recalls of a set he performed in Boston in his high school years. Adam Sandler details bizarre heckle from 'devastatingly bad' early standup gig in exclusive My Next Guest clip &34;It was five minutes of just silence,&34; the &34;Happy Gilmore&34; star recalls of a set he performed in Boston in his high school years. By Wesley Stenzel :maxbytes(150000):stripicc()/WesleyStenzelauthorphoto32b61793a2784639af623f2ae091477e.jpg) Wesley Stenzel is a news writer at . He began writing for EW in 2022.

"It was five minutes of just silence," the "Happy Gilmore" star recalls of a set he performed in Boston in his high school years.

Adam Sandler details bizarre heckle from 'devastatingly bad' early stand-up gig in exclusive My Next Guest clip

"It was five minutes of just silence," the "Happy Gilmore" star recalls of a set he performed in Boston in his high school years.

By Wesley Stenzel

Wesley Stenzel is a news writer at **. He began writing for EW in 2022.

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November 24, 2025 12:00 p.m. ET

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Adam Sandler and David Letterman on 'My Next Guest Needs No Introduction'. Credit:

Every comedian has to contend with hecklers — and Adam Sandler still remembers a particularly strange jeer from his teenage stand-up days.

In an exclusive clip from his upcoming conversation with David Letterman on Netflix's *My Next Guest Needs No Introduction*, the *Happy Gilmore* star details one of his earliest live comedy gigs in Boston.

"I was devastatingly bad, and nobody laughed," Sandler remembers. "It was five minutes of just silence, and at the very end, I heard a man say, 'He's wearing a retainer!' And that was it."

Sandler got the gig thanks to his older brother. "I was a high school kid, I did stand-up," he explains. "[My brother] was going to Boston University, and he said, 'There's comedy nights at clubs in town. You should do that.' I said, 'Yeah, yeah, yeah. Good.'"

The commitment snuck up on the *Jay Kelly* star. "One night we're eating dinner with my family and he says, 'You ready to do that stand-up comedy thing?'" Sandler says. "And I said, 'Yeah, when is that?' And he goes, 'Tonight. I told you.'"

Sandler's brother also asked if he knew what he'd joke about during his stand-up slot. "I said, 'No, no, no, I don't,'" the comedian recalls. "He goes, 'All right, well it's five minutes.' I said, 'Oh, all right, I can do that. I'll talk about grandma.'"**

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The *Billy Madison* actor says that "around my house, I would try to sound like my grandmother and make my father laugh," so he decided to bring that impression to the stage in Boston.

Letterman asks to "hear a little grandma now," and Sandler obliges with a particularly memorable anecdote.

"This was a big story in my house," he says. "I was in Florida visiting. And I took a shower in the morning and I did my day, and then that night I was taking another shower. And my grandmother said, 'You take a lot of showers!' And I said, 'Yes, yes.' And she goes, 'I think you're masturbating in there.'"

Adam Sandler in at a 'Jay Kelly' screening in Los Angeles.

JC Olivera/Getty

Sandler regrets that he didn't use that anecdote during his disastrous Boston set. "I should've," he says. "That was a big, famous story in my house."

***Get your daily dose of entertainment news, celebrity updates, and what to watch with our EW Dispatch newsletter.***

Season 6 of* My Next Guest Needs No Introduction With David Letterman* hits Netflix in December. Sandler's episode drops Dec. 1.

The show is executive produced by Tom Keaney and Mary Barclay for Worldwide Pants; Justin Wilkes, Michael Steed, Isabel Richardson, and Yolanda T. Cochran for Jax Media/Imagine Entertainment. The series is produced by Tommy Alter, John Nemeth and Hunter Speese for Jax Media/Imagine Entertainment.**

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Source: "EW Talk"

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Source: Talk

Published: November 25, 2025 at 08:57AM on Source: RON MAG

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