During the 2025 Academy Awards, Conan O’Brien kicked off the ceremony with a sharp exchange featuring longtime friend Adam Sandler, which quickly became one of the most talked-about moments of the evening. Sandler’s choice of attire—a blue hoodie and gym shorts—became the center of attention as O’Brien, known for his quick wit, remarked, “What are you wearing?”
Sandler, dressed in his usual relaxed fashion, responded by saying, “Nobody even thought about what I was wearing until you brought it up,” before walking off stage in mock protest. In a playful twist, Sandler hugged actor Timothée Chalamet on his way out, before claiming, “I’m a good person” in defense of his casual look.
What seemed like a simple back-and-forth about fashion, however, quickly took on deeper significance. O’Brien and Sandler’s exchange subtly echoed a moment from just days before, when Ukrainian President Volodymyr Zelensky visited the White House.
At that meeting, Zelensky, wearing military fatigues, was asked why he wasn’t dressed more formally. He responded that he would wear a suit “when the war is over,” a line that resonated with many watching. Former President Donald Trump, standing beside Zelensky, defended the choice, saying that the outfit was fitting given the circumstances.
O’Brien and Sandler’s skit played off this real-world moment, using Sandler’s outfit and the playful back-and-forth to comment on the ongoing discussion about what constitutes appropriate attire in public settings. By having Sandler wear his familiar, casual style, the two men offered a cheeky critique of the expectations surrounding formal dress, especially at high-profile events like the Oscars.
The humor was underscored by the audience’s quick recognition of the reference to Zelensky’s visit, blending a lighthearted Hollywood moment with a timely commentary on global events. O’Brien’s line about Sandler looking like “a guy playing video poker at 2 a.m.” added another layer of humor to the bit, poking fun at the contrast between the glitzy world of Hollywood and Sandler’s laid-back vibe.
Sandler’s neon blue hoodie, priced at $175, quickly became a sensation after the Oscars aired. The garment, from the brand Aviator Nation, sold out soon after the monologue, reflecting both Sandler’s influence on popular culture and the growing acceptance of more casual fashion in high-profile settings.
While the bit had its comedic roots in the longstanding friendship between O’Brien and Sandler, it also served as a commentary on broader cultural shifts, particularly the evolving norms around dress codes. As casual wear continues to make its mark at events once defined by tuxedos and gowns, this Oscars moment captured the intersection of humor, style, and social commentary.
