On March 2, Hollywood’s A-list worked the red carpet outside of Los Angeles’s Dolby Theatre, ahead of the 97th Academy Awards that honors the best of the best in Hollywood.

Making their style statements at the last big awards bash of the season, stars pulled out all the stops with their most spectacular looks that included dramatic silhouettes, sweeping gowns, custom suits and a whole lot of sparkle.

And then there was Adam Sandler.

Comfy and casual
“For such a prestigious night, it’s important that everyone is properly dressed, okay?” said TV funnyman Conan O’Brien, 61, who was hosting the 2025 Oscars. “You’re dressed well…Adam…”

During his highly anticipated opening monologue, O’Brien took some shots at Sandler, who was seated in the audience, surrounded by elegant celebrities in their best Oscars’ outfits.

“Conan, what’s up my brother?” said the 58-year-old star of Happy Gilmore, who was sitting in an aisle seat, his head covered by the hood of the light blue sweatshirt that he wore with some shorts and Steph Curry Kicks. “What’s going on, man?”

After O’Brien asks Sandler what he’s wearing, the comedian stutters a bit and strikes back, saying: “Nobody even thought about what I was wearing until you brought it up.”

O’Brien then tells the star of 50 First Dates, “You’re dressed like a guy playing video poker at 2 a.m., Adam.”

Defending himself in typical Sandler style, the Grown Ups star argued, “You know what, I like the way I look, because I’m a good person. I don’t care about what I wear or what I don’t wear. If my snazzy gym shorts and fluffy sweatshirt offend you so much that you had to mock me in front of my peers…”

Swiftly apologizing from the stage, O’Brien feigned remorse and looked down at the podium that he stood behind.

Rising to this feet, Sandler told the audience: “I’m going. I’m leaving, I have to!”

As the crowd shouted, “no!” and begged him to stay, the comedian joked, “No, it’s not you, it’s him.”

Pointing at O’Brien, who was trying to contain his laughter through the hilarious exchange, Sandler then said, “You caused this!”

Before leaving the ceremony, Sandler told the crowd: “You are all welcome to join me for a game of five-on-five basketball at Veteran Park tonight. Midnight tip-off. The guy from Nosferatu, he’s on my team,” he joked.

Golden Globes nod
Next, Sandler walked down the aisle towards 29-year-old Timothée Chalamet, who was nominated for his performance in the 2024 film, A Complete Unknown.

“And one more thing. CHALAMET!” Sandler shouted in the actor’s ear, before giving him a hug and leaving the Dolby theatre to the resounding applause from the audience.

This playful moment was a nod to the Golden Globes earlier this year when host Nikki Glaser joked that Chalamet’s name sounded like something Sandler would say in one of his signature over-the-top voices.

Glaser put Sandler on the spot, asking him to say Chalamet’s name out loud – and of course, he delivered in classic Sandler style, earning plenty of laughs.