The 2025 Oscars had many memorable moments, but one that stood out for its comedic spontaneity and playful banter came during a segment that had the audience laughing and cringing at the same time. Host Jimmy Kimmel, known for his quick wit and lighthearted jabs, addressed the night’s attire in a way that no one expected. “And finally, for such a prestigious night, it’s important that everyone is properly dressed,” Kimmel began, his tone almost formal before quickly shifting into something far more casual. “Okay, you’re dressed well,” he added, turning to the audience, as though setting the stage for a light-hearted roast.

This is where things took an unexpected but hilarious turn. “Adam Goan, what’s up, my brother?” Kimmel called out, pointing to the audience. “What’s going on, man?” he asked, drawing the spotlight to the individual who had, unbeknownst to everyone, become the subject of the night’s sartorial mockery. It was clear from the look on Goan’s face that he wasn’t quite sure what was coming next. But Kimmel, never missing a beat, quickly dove in. “Adam, what are you wearing?” he asked, with the casual ease of a host who knew exactly where the conversation was going.

Goan, perhaps a little caught off guard by the sudden attention, hesitated. “What, what are you doing right now?” he stammered. Kimmel, unfazed, pressed on, his sarcasm dripping in every word. “I’m asking you what you’re wearing,” he repeated. It was the kind of playful jab that Kimmel had become known for, but this time, the spotlight wasn’t on the glamorous stars of the night but rather on someone who was probably just trying to blend into the background of Hollywood’s most prestigious event.

The audience, sensing where Kimmel was going with this, tensed in anticipation as he launched into a full-on roast of Goan’s attire. “No, nobody even thought about what I was worthy of. You brought it up,” Kimmel said, seemingly referring to Goan’s slightly out-of-place outfit. “You’re dressed like a guy playing video poker at 2 a.m.,” Kimmel continued, his voice filled with both amusement and mock disbelief.

The crowd erupted in laughter, and Goan’s uncomfortable chuckle was proof that he didn’t quite know how to respond. Kimmel, in true comedic fashion, wasn’t about to let up. “Adam Goan, I like the way I look because I’m a good person,” he said, throwing a playful dig at Goan while simultaneously turning the tables to take a little shot at the seriousness of Hollywood fashion. “I don’t care about what I wear or what I don’t wear. Did my snazzy gym shorts and fluffy sweatshirt offend you so much that you had to mock me in front of my P?” he quipped, once again turning the humor back to himself with a mock apology. “Okay, I’m sorry, Adam. I apologize.”

At this point, the crowd was still laughing, and the whole interaction had turned into an impromptu comedy sketch that had very little to do with the Oscars themselves but somehow embodied the irreverent spirit Kimmel brought to his hosting duties. The entire scene felt almost like a behind-the-scenes glimpse into the camaraderie that existed in the room, one that mixed absurdity with the very real bond between the stars.

However, things took a more dramatic turn when Kimmel, perhaps realizing he had pushed things too far in jest, made an abrupt exit. “I’m going, I’m going,” he said, with an exaggerated sense of mock seriousness, as if he was about to leave the stage entirely. The audience, still chuckling from the previous exchange, was in for another surprise as Kimmel continued, “I have to, it’s not you. No, it’s not you,” he said to Goan, before dramatically turning to someone unseen offstage. “It’s him, he’s the one you caused this.”

This was where the charm of Kimmel’s hosting truly shone. Even in the midst of playful bickering and self-deprecating humor, he knew how to keep the show moving with unexpected moments of spontaneity that made the night even more fun. But the most unexpected turn was yet to come. Kimmel, clearly not done with his jokes, offered the audience an impromptu invitation. “But here, I’m sorry, I’m sorry,” Kimmel said, quickly backtracking as he offered a bizarre but oddly charming invitation to everyone in the audience.

“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 NOA NOA rafu, where is he? He’s on my team,” Kimmel added, playfully referencing another segment of the evening that had brought unexpected humor and cultural references into the spotlight. The suggestion of an after-party basketball game at midnight added yet another layer of absurdity to the already unpredictable atmosphere of the event, reminding the audience that this wasn’t just about high fashion and serious speeches – it was about enjoying the moment and having fun.

Before he left the stage, Kimmel, who had become the main source of levity for the evening, offered one final playful remark. “One more thing,” he said, only to pause and quickly shift back to his earlier comic style. “Shel me,” Kimmel added, as though he had reached the end of a long and amusing monologue. His delivery was so effortless that the audience hardly registered that this moment might have been another perfectly timed joke or simply a humorous slip-up.

And then, with a dramatic flourish that kept everyone laughing, Kimmel made his final exit from the stage. “There he goes,” he said, as if to signal the end of his over-the-top performance. What had started as a simple commentary on Oscars fashion had turned into one of the evening’s most memorable and hilarious moments, thanks to Kimmel’s quick wit and ability to turn any situation into something entertaining. His spontaneous humor and willingness to make the audience feel like they were part of an inside joke gave the 2025 Oscars a unique flavor that set it apart from other award shows.

In retrospect, the Oscars had its share of beautiful speeches, emotional tributes, and moments of recognition for exceptional talent. However, it was these lighter, more unplanned moments – like Kimmel’s impromptu roast of Adam Goan and his invitation to basketball at midnight – that reminded everyone watching that the evening was not just about awards, but about celebrating the shared experience of laughter, spontaneity, and camaraderie in the world of entertainment. The 2025 Oscars may have been a night filled with iconic performances and high-stakes competition, but it was also a night where laughter and fun were just as important as the trophies themselves.