Adam Sandler’s laid-back style became the punchline at the Oscars, leading to a dramatic exit after Conan O’Brien took aim at his signature casual look.
The 58-year-old comedian, known for skipping formalwear at award shows, found himself in the spotlight when O’Brien playfully highlighted his fashion choices before sharing a hilarious moment with best actor nominee, Timothée Chalamet.
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While presenting a montage of early Hollywood headshots, O’Brien praised the stars for dressing appropriately—before pointedly pausing and turning to Sandler, who stood out in an aqua blue hoodie, basketball shorts, and sneakers.
"Conan. What's up my brother? What's going on, man?" the Happy Gilmore star said, before O'Brien ribbed him and asked, “Adam, what are you wearing?”
"What are you doing right now?” Sandler asked, as O'Brien repeated, “I'm asking you what are you wearing?"
As the back and forth continued about his choice of attire, the Hollywood star yelled at O’Brien in faux outrage: “Nobody even thought about what I was wearing until you brought it up.
“I like the way I look. Because I’m a good person; I don’t care about what I wear and what I don’t wear [and that] my snazzy gym shorts and fluffy sweatshirt offend you so much that you had to mock me in front my peers!”
As the witty exchange continued, O'Brien then attempted to retract his criticism but Sandler got up in mock exasperation and started walking out of the crowd at the Dolby Theater in Los Angeles.
“You caused this!” Sandler joked, pointing at O’Brien as the audience laughed.
Referencing Willem Dafoe’s eerie role in Nosferatu, he added: “You’re all invited to a five-on-five game at Veteran Park. Midnight tip-off. The guy from Nosferatu is on my team.”
Before making his exit, Sandler took a detour to Oscar nominee Timothée Chalamet, calling out, “And one more thing, CHALAMET!” before hugging him—an inside joke that had roots in a hilarious moment from the Golden Globes.
At the Globes, host Nikki Glaser had joked that Chalamet’s name sounded like something Sandler would say in one of his signature exaggerated voices.
She then put him on the spot, prompting him to say it aloud—which he happily did, in full Sandler style.
Elsewhere, Anora dominated this year’s Oscars, taking home the award for Best Picture, Best Actress for Mikey Madison, and Best Director for Sean Baker.
The independent film tells the story of a sex worker who dances at a strip club and meets — and marries — the son of a Russian oligarch. It takes a human-centred approach to filmmaking, focusing on themes of identity, resilience and a complex journey towards self-discovery.
Accepting the win, director Baker said: “I want to thank the Academy for recognising a truly independent film.”
Earlier in the night, an emotional Zoe Saldana broke down in tears as she picked up the award for Best Supporting Actress for her role in Emilia Perez, while Kieran Culkin was honoured as Best Supporting Actor.
While Adrien Brody picked up Best Actor for his turn in The Brutalist but he came under fire for his speech.
Conclave, Wicked, The Substance, Emilia Pérez, and Dune: Part Two each took home awards. Read the full list of winners here.
