Adam Sandler stole the spotlight at the 2025 Oscars in a lighthearted and comedic moment that had everyone laughing. Known for his roles in Happy Gilmore and Grown Ups, Sandler’s unconventional outfit at Hollywood’s most prestigious event was called out by host Conan O’Brien during the opening monologue, causing a playful exchange that amused the star-studded crowd at the Dolby Theatre.
A Casual Look at the Oscars
On March 2, as Hollywood’s elite walked the red carpet in their most glamorous outfits, Adam Sandler took a decidedly different approach. While fellow stars donned dramatic silhouettes, sweeping gowns, and custom suits, Sandler opted for a much more casual look: a light blue sweatshirt with a hood, gym shorts, and sneakers—specifically, Steph Curry kicks.
The 58-year-old comedian, who was seated among the elegantly dressed celebrities, certainly made a fashion statement of his own. However, this unconventional choice didn’t go unnoticed by the Oscars’ host, Conan O’Brien, who couldn’t resist poking fun at Sandler’s laid-back attire.
Conan O’Brien Takes a Shot at Sandler
As part of his opening monologue, O’Brien, 61, took a playful jab at Sandler for his casual look. “For such a prestigious night, it’s important that everyone is properly dressed, okay?” O’Brien quipped, directing the comment toward Sandler. He then added, “You’re dressed well… Adam…” This set the stage for the back-and-forth that would follow.
Sitting in an aisle seat with his hood up, Sandler responded humorously, “Conan, what’s up, my brother?” O’Brien couldn’t resist continuing the light-hearted roast, asking Sandler what he was wearing. Sandler, always quick with a comeback, responded: “Nobody even thought about what I was wearing until you brought it up.”
O’Brien then jokingly compared Sandler’s outfit to that of someone playing video poker at 2 a.m., saying, “You’re dressed like a guy playing video poker at 2 a.m., Adam.” The crowd laughed, but Sandler wasn’t having it. In typical Sandler fashion, he defended his look, saying, “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.”
The Comedy That Followed
With his usual charm, Sandler continued, “If my snazzy gym shorts and fluffy sweatshirt offend you so much that you had to mock me in front of my peers…” The audience couldn’t help but laugh at the playful exchange, and O’Brien quickly apologized for his jest, pretending to feel remorse for embarrassing Sandler.
However, the fun didn’t stop there. Rising to his feet, Sandler jokingly announced, “I’m going. I’m leaving, I have to!” The audience erupted in cheers and shouts of “no!” as they begged him to stay. Sandler, in true comedic fashion, pointed at O’Brien and said, “It’s not you, it’s him,” humorously blaming O’Brien for causing his exit.
Before making his way out of the ceremony, Sandler added, “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,” keeping the mood light and playful.
A Nudge to Timothée Chalamet
As Sandler made his way toward the exit, he stopped by actor Timothée Chalamet, who was nominated for his performance in A Complete Unknown. Sandler, never missing an opportunity for humor, shouted, “And one more thing. CHALAMET!” into the actor’s ear, before giving him a big hug. The audience erupted in applause as Sandler left the Dolby Theatre, his exit as memorable as his entrance.
This playful moment was also a nod to the Golden Globe Awards earlier in the year when host Nikki Glaser joked about how Chalamet’s name sounded like something Sandler would say in one of his exaggerated voices. During that show, Glaser put Sandler on the spot and asked him to pronounce Chalamet’s name, which he did in his classic over-the-top style, earning laughs from the audience.
A Fun, Lighthearted Moment at the Oscars
While many view the Oscars as a serious and glamorous event, Adam Sandler’s humorous antics reminded everyone that laughter is just as important on Hollywood’s biggest night. His carefree attitude and witty responses made for an unforgettable moment during an evening filled with star-studded glamour. Though his outfit was unconventional for the occasion, it was clear that Sandler was enjoying the fun, and his lighthearted humor provided a welcome break from the usual formality of the awards show.
Conclusion: A Moment of Laughter
Adam Sandler’s playful exchange with Conan O’Brien at the 2025 Oscars was a standout moment, showing that even at one of the most prestigious events in Hollywood, humor and spontaneity still have a place. Whether it’s Sandler’s casual outfit or his quick-witted comebacks, the comedian reminded the audience that not everything has to be taken too seriously, even at the Academy Awards.
What did you think of Sandler’s playful behavior at the Oscars? Do you think it added to the fun of the evening, or was it an unwelcome distraction? Share your thoughts with us, and don’t forget to share this hilarious moment with your friends and family!
