Adam Sandler made quite the impression at the 97th Academy Awards, but not for the usual reasons. The Happy Gilmore star found himself at the center of a comedic exchange with Oscars host Conan O’Brien, who couldn’t help but poke fun at Sandler’s signature laid-back style. The result? A hilarious moment that had the audience in stitches as Sandler jokingly stormed out of the Dolby Theatre.

Hollywood’s Best Dressed… and Then There’s Sandler

On March 2, Los Angeles’ Dolby Theatre was packed with Hollywood’s biggest stars, all dressed to the nines for one of the most prestigious nights in the film industry. As celebrities dazzled in custom couture, flowing gowns, and perfectly tailored tuxedos, Adam Sandler opted for something a little less… conventional.

Wearing a light blue hoodie, gym shorts, and a pair of Steph Curry sneakers, the Grown Ups star was a stark contrast to the glitz and glamour surrounding him. Naturally, O’Brien, who was hosting the awards for the first time, couldn’t resist calling him out.

Conan O’Brien Roasts Sandler’s Casual Look

During his opening monologue, O’Brien, 61, turned his attention to Sandler, seated comfortably in an aisle seat among the elegantly dressed attendees.

“For such a prestigious night, it’s important that everyone is properly dressed, okay?” O’Brien quipped before singling out Sandler. “You’re dressed well… Adam…”

The camera zoomed in on the 58-year-old comedian, who simply shrugged and responded, “Conan, what’s up my brother?” as he lounged in his seat, hoodie up.

When O’Brien asked about his choice of attire, Sandler stammered for a moment before replying, “Nobody even thought about what I was wearing until you brought it up.”

Unfazed, O’Brien continued, “You’re dressed like a guy playing video poker at 2 a.m., Adam.”

Sandler, staying true to his self-deprecating humor, defended his look. “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…”

O’Brien feigned remorse, bowing his head at the podium as laughter erupted throughout the room.

Sandler’s Dramatic ‘Exit’ Steals the Show

As the crowd continued laughing, Sandler suddenly stood up and declared, “I’m going. I’m leaving, I have to!”

The audience playfully protested, shouting “No!” and urging him to stay. Sandler, ever the showman, dramatically pointed at O’Brien and said, “No, it’s not you, it’s him! You caused this!”

While O’Brien tried to keep a straight face, the moment was too funny to contain, and he broke into laughter along with the rest of the room.

Before making his grand exit, Sandler made sure to leave on a high note. “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, earning even more applause.

A Nod to the Golden Globes and a Chalamet Cameo

As Sandler made his way down the aisle, he stopped beside A Complete Unknown star Timothée Chalamet. Without missing a beat, he leaned in and shouted, “CHALAMET!” directly into the 29-year-old actor’s ear before pulling him in for a hug.

The moment was a callback to the 2024 Golden Globes when host Nikki Glaser had jokingly pointed out that Chalamet’s name sounded like something Sandler would say in one of his signature exaggerated voices. When Glaser put him on the spot to say it out loud, Sandler delivered, much to the audience’s delight.

A Staged but Hilarious Oscars Moment

While the interaction between O’Brien and Sandler was undoubtedly staged, it didn’t make it any less entertaining. The Oscars have long been known for their scripted comedy bits, and this one was a highlight of the night, reminding fans why Sandler remains one of Hollywood’s most beloved funnymen.

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