Adam Sandler Says His Love Life “Flatlined” Next to George Clooney — and Reflects on Fame, Friendship, and Their New Film Together

Adam Sandler has opened up about the surprisingly humbling moment he realized the sheer magnitude of George Clooney’s star power — a memory that left the comedian feeling “invisible” at the height of the ER frenzy in the mid-1990s.

In a new interview with The New York Times, the Happy Gilmore star, now 59, recalled first meeting Clooney on Saturday Night Live in 1995. Not long after, the pair attended a New York Knicks game together — and Sandler admits the experience was eye-opening.

“It was at the height of ER, and I went to a Knicks game with George,” Sandler said. “I remember feeling as invisible as I’ve ever felt. I thought I was becoming a star, and I was like, ‘Oh, not a soul’s looking at me.’”

He added that Clooney, then 34 and considered one of the most desirable men in the world, drew the attention of everyone in the arena:

“Every woman in the place was looking at him, every guy’s going, ‘Man, I wish I was that guy.’”

This was during the period when Clooney portrayed Dr. Doug Ross on NBC’s smash-hit medical drama ER, a role he held from 1994 to 1999. The show dominated ratings, launched his career into Hollywood superstardom, and is still regarded as one of the most influential dramas of its era. (BBC Entertainment)

Adam Sandler and George Clooney attend the “Jay Kelly” Red Carpet during the 63rd New York Film Festival at Alice Tully Hall, Lincoln Center on September 29, 2025.

Clooney Sees the Memory Through a Different Lens

Clooney, now 64, remembered the outing far more fondly.

“That was really fun,” he said.
“We’ve always kept in touch, but never found a project. Then Noah called.”

The “Noah” he refers to is filmmaker Noah Baumbach, who has finally brought the two longtime friends together on screen.

Sandler and Clooney will co-star in Baumbach’s 2025 coming-of-age drama Jay Kelly, marking their first major collaboration after decades in the industry. (The Hollywood Reporter)

George Clooney and Adam Sandler attend the AFI FEST 2025 on October 23, 2025.

Clooney Reflects on Fame — and His Aunt’s Struggles

In the same interview, Clooney opened up about the darker side of fame, referencing the turbulent career of his aunt, legendary 1950s singer Rosemary Clooney.

“I’d seen it from the point of view of my aunt. She was a big star in the ’50s, then pop music changed, and she was out of business,” Clooney said.
“She didn’t handle it well and lost about 30 years on drugs and booze, being pretty angry at life.”

He said watching her decline taught him to stay grounded:

“It’s a great lesson because you understand how little [fame] has to do with you and that there is no success at all without massive amounts of failure.”

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Sandler on His Own Journey: “Just keep going.”

Sandler recalled his early years struggling through auditions that went nowhere.

“It didn’t ever get in my way,” he said. “Because I was young, and I was like, ‘All right, keep going. Go, go, go, until it happens.’”

That persistence ultimately paid off, leading to a decades-long career in film and comedy, including hits like The Wedding Singer, Murder Mystery, and Uncut Gems.

George Clooney, Adam Sandler in “Jay Kelly.”

A Friendship That Has Lasted Decades

In an interview with People in October, Sandler spoke warmly of his bond with Clooney:

“He loves his friends. We are good friends now, George and I. I love him.”

Sandler recalled time spent vacationing, playing sports, and sharing stories about childhoods that — despite the fame — were surprisingly similar:

“It’s a very similar kind of upbringing in the fact that our buddies were important to us.”

Clooney, for his part, has a long history of keeping close with friends from his early days as a rising star.

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Clooney Still Close With His ER Castmates

In 2022, Clooney revealed on The Drew Barrymore Show that he remains tight with many of his ER co-stars — more than two decades after the show ended.

“I guess it was the friendship I have with all of them and that I continue to have.”

He said Anthony Edwards (Dr. Mark Greene) and his wife had recently visited him in Italy, and confirmed he stays close with Julianna Margulies and Noah Wyle:

“They’re really good friends. That show was the job of a lifetime. And it changed my career.”

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The ER Universe Continues — With Legal Drama

While fans have long speculated about an ER reboot, former executive producer John Wells told Deadline in 2019 that a revival would require “a really interesting idea” to move forward.

But in 2024, the legacy of ER became complicated when ER creator Michael Crichton’s widow, Sherri Crichton, filed a lawsuit alleging that the Max series The Pitt — starring and executive produced by Noah Wyle — was essentially an unauthorized reboot.

George Clooney as Dr. Doug Ross in “ER.”

According to the lawsuit:

“The Pitt is ER. It is not like ER, it is ER.”
(Variety)

Wyle, who starred on ER from 1994 to 2009, pushed back on the claims, saying:

“This taints the legacy, and it shouldn’t have.”
“At one point this could have been a partnership… but now I’ve never felt less celebratory of the 30th anniversary of ER than I do this year.”

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Two Icons, Three Decades Later

Despite the ups and downs of fame, legal battles surrounding their old projects, and the evolution of their careers, both Sandler and Clooney now find themselves working together for the first time — a full-circle moment that fans could only have dreamed of.

Their upcoming film Jay Kelly marks more than another chapter in their careers; it represents decades of friendship, resilience, and reinvention — the very qualities that have kept both men at the top of Hollywood for so long.