The 97th Academy Awards kicked off with a bang on March 2, 2025, at the Dolby Theatre in Hollywood, and no one could have predicted the comedic chaos that unfolded when host Conan O’Brien set his sights on Adam Sandler. Known for his laid-back vibe, Sandler strolled into the star-studded event in a bright blue hoodie, gym shorts, and sneakers—a stark contrast to the glitz and glamour of the Oscars red carpet. What followed was a side-splitting exchange that stole the show, proving once again why Conan was the perfect pick to helm Hollywood’s biggest night. Here are 15 realism-inspired highlights from this unforgettable moment—and we’re dying to know what you think in the comments on our Facebook page!
1. A Sweatshirt That Screams Sandler
Sandler’s $175 Aviator Nation hoodie wasn’t just casual—it was a neon blue beacon in a sea of tuxedos, instantly catching Conan’s eye and setting the stage for hilarity.
2. Conan’s Razor-Sharp Opener
“You’re dressed like a guy playing video poker at 2 a.m.,” Conan quipped from the stage, his deadpan delivery slicing through the room like a comedic sword.
3. Sandler Fires Back
“Nobody even thought about what I was wearing until you brought it up!” Sandler yelled, his raspy voice dripping with mock indignation as the crowd erupted.
4. The “Good Person” Defense
“I like the way I look because I’m a good person,” Sandler declared, leaning into his everyman charm with a grin that dared Conan to keep going.
5. Gym Shorts as a Statement
Those “snazzy gym shorts” weren’t just comfy—they became a symbol of Sandler’s refusal to bow to Hollywood’s dress code, and fans loved it.
6. A Fluffy Sweatshirt Feud
“Did my fluffy sweatshirt offend you so much that you had to mock me in front of my peers?” Sandler asked, turning a fashion jab into a full-on roast.
7. The Fake Walkout
In true Sandler fashion, he stormed out—or pretended to—leaving the audience shouting “No!” as he waved goodbye with theatrical flair.
8. Chalamet Gets a Shout
Before exiting, Sandler bolted to Timothée Chalamet, bellowing “Chalamet!” in his ear and wrapping him in a bear hug—a nod to their Golden Globes moment.
9. Basketball After-Party Invite
“You’re all welcome to join me for a five-on-five basketball game at Veteran Park tonight, midnight!” Sandler shouted, turning the Oscars into a pickup game pitch.
10. Conan’s Apology (Sort Of)
Conan faux-apologized, saying, “I’m sorry, Adam, I didn’t mean to ruin your night,” but the twinkle in his eye said otherwise.
11. Audience Reaction in Real Time
The Dolby Theatre shook with laughter, with stars like Ariana Grande and Cynthia Erivo visibly cracking up at the chaos.
12. A Nod to Realism
Sandler’s outfit wasn’t just funny—it mirrored his real-life persona, making the bit feel like a peek into his off-screen world.
13. Social Media Explodes
Posts on X lit up with fans praising Conan’s jab and Sandler’s response, with one calling it “the most Sandler moment ever.”
14. Fashion Meets Function
Those sneakers weren’t just for show—Sandler looked ready to hit the court, blending realism with his comedic exit plan.
15. A Night to Remember
This wasn’t just a roast—it was a masterclass in live TV comedy, cementing Conan and Sandler as the night’s MVPs.
What’s Your Verdict?
The 2025 Oscars proved that realism doesn’t need a script—just a hoodie, some guts, and a quick wit. Did Conan’s roast make your night, or was Sandler’s comeback the real winner? Head to our Facebook page and drop your thoughts in the comments—we can’t wait to see what you loved most about this epic Oscars moment!
