The 2025 Oscars, held on March 2, saw host Conan O'Brien deliver a standout performance, particularly highlighted by his hilarious exchange with Adam Sandler, who made a memorable cameo during the ceremony. Dressed famously in his typical blue zip-up hoodie and baggy basketball shorts, Sandler's choice of attire drew attention amid the sea of glamorous tuxedos and formal gowns.
During the first half hour of the event, O'Brien couldn't resist poking fun at Sandler's non-conventional outfit. “You’re dressed like a guy playing video poker at 2 a.m., Adam,” O’Brien quipped, setting the tone for their comedic interaction. Sandler, ever quick-witted, shot back, “Nobody even thought about what I was wearing until you brought it up!” His response elicited laughter from the audience, echoing his signature blend of humor and self-deprecation.
O'Brien later revealed the backstory behind this funny exchange, stating, “I made the idea for Sandler. And then...Adam and I are old friends. I called him up, and he liked the idea. And then he said, 'I have another idea,' and it involved him dressing in the way he’s most comfortable.” This shift to Sandler's idea for the outfit emphasized his preference for comfort over traditional formality, which has often been his signature approach.
Sandler's casual style has always set him apart as one of Hollywood's most beloved comedic figures, and his Oscars 2025 appearance was no different. O'Brien's playful jests about various celebrities, including Best Actress nominee Karla Sofía Gascón and Antonio Banderas, added to the lighthearted atmosphere of the evening. ScreenRant's Mary Kassel even praised O'Brien's hosting abilities, stating, “He brought a refreshing lightness and sincerity to the night without ignoring the complicated issues facing the U.S. and the future of Hollywood.”
The interaction reached its comedic pinnacle when Sandler, feigning mock exasperation at O'Brien's comments, rose from his seat at the Dolby Theatre. “I’m going. Off I go. I’m leaving!” he exclaimed dramatically, prompting more laughter from the crowd.
Not to be outdone, Sandler invited fellow attendees to join him for some light-hearted fun post-ceremony, humorously proposing, “You are all welcome to join me for a game of 5-on-5 basketball at Veterans Park tonight, midnight tip-off.”
Adding another layer to his cameo, Sandler recalled a joke from the Golden Globes when Nikki Glaser had joked about Timothée Chalamet’s last name. Prior to departing the stage, he circled back to Chalamet’s seat and shouted, “Chalameeeeeeet!” making everyone chuckle, quickly bridging his spontaneous humor with the earlier night’s banter.
The memorable appearance solidified Sandler's recognizable style and humor, both of which have been key elements throughout his career. Despite his unconventional wardrobe choices, Sandler’s comedic spirit shone through, engaging both the live audience and those watching at home. His upcoming film, Happy Gilmore 2, set to premiere later this year on Netflix, promises to showcase more of his classic antics.
The combination of O'Brien's comedic flair and Sandler's unique approach to Hollywood norms created moments of levity during the Oscars. Their chemistry exemplified the relatable humor fans appreciate, reinforcing Sandler's belief: “I like the way I look because I’m a good person. I don’t care about what I wear.”
With these unforgettable comedic highlights, the 2025 Oscars presented not just awards but also showcased the extraordinary camaraderie and humor between two of Hollywood’s beloved entertainers, leaving viewers eagerly awaiting more from them both.