10 Wildest Viral Moments From the Oscars 2026 — Including Conan O'Brien's Savage Dig at Donald Trump's 'Small' Manhood

That's a wrap on the Oscars 2026!

Hollywood's biggest night, hosted by Conan O'Brien, honored the best stars in the industry at Dolby Theatre on March 15. From the arrivals to press room, the event delivered plenty of viral moments.

Shark Tank star Kevin O'Leary was business as usual, revealing to Variety he wagered money on Timothée Chalamet to win the Academy Award for Best Actor in a Leading Role.

He disclosed, "I just put 1,000 bucks on Kalshi walking in here that he's going to win. Because I know the voting stopped long before that controversy happened."

O'Leary referenced the Wonka star's controversial comment about certain performing arts.

"He's a really great guy, his mother's really nice," he added. "The kid is a great kid. He took a b-- rap on that. By the way, he gave a lot of promo to opera houses and ballet."

No one was spared from O'Brien's hilarious — and scathing — monologue at the Oscars 2026. The host poked fun at the venue's name by welcoming the audience to the "Has a Small P---- Theatre."

"Let's see him put his name in front of that!" he alluded to Donald Trump's manhood size, shading the president after the Kennedy Center Board of Trustees voted to rename the John F. Kennedy Center for the Performing Arts to The Donald J. Trump and The John F. Kennedy Memorial Center for the Performing Arts.

Leonardo DiCaprio also had a moment in the spotlight when O'Brien asked him to create a new viral meme. The camera panned to the What's Eating Gilbert Grape actor as the caption "TFW [that feeling when] You Didn't Agree to This" appeared at the bottom of the screen.

DiCaprio, as the King of Memes, humorously feigned confusion to play along with the joke.

The Oscars 2026 honored KPop Demon Hunters with the Best Animated Feature award.

"Thank you to the Academy and to all fans who got us here, and for those of you who look like me," director Maggie Kang said in her acceptance speech. "I'm so sorry that it took us so long to see us in a movie like this. But it is here. And that means that the next generations don't have to go longing. This is for Korea and for Koreans everywhere."

Kang and producer Michelle L.M. Wong made history as the first female Asian winners in the category.

The hit Netflix show also won Best Original Song.

For the seventh time in Oscars history, the ceremony honored two winners for Best Live Action Short.

After The Singers won, Kumail Nanjiani announced Two People Exchanging Saliva was also a recipient of the award.

"Ironic that the short film Oscar is going to take twice as long," he said.

Avengers, assemble!

Fourteen years after the first The Avengers film was released, Robert Downey Jr. and Chris Evans reunited to present the Oscars for Best Adapted and Original Screenplay.

"The script. It's the driving force of any film, and it's truly been a banner year for screenwriters," Downey Jr. said.

They exchanged gifts, with the Captain America star giving Downey Jr. a signed copy of the Avengers script and the Iron Man actor gifting Evans his valet receipt.

Melissa McCarthy, Kristen Wiig, Rose Byrne, Ellie Kemper and Maya Rudolph took the stage together for a hilarious reunion15 years after Bridesmaids was released. The quintet handed the Oscar for Best Score to Sinners.

Michael B. Jordan won his first Oscar for Best Actor for his role in Sinners, outshining DiCaprio, Chalamet Ethan Hawke and Wagner Moura.

He thanked his family before expressing his gratitude to director Ryan Coogler, whom he called "an amazing, amazing person."

"I'm so honored to call you a collaborator and a friend, and you gave me [the] opportunity and space for me to be seen. I love you too, bro. Love you to death," he said.

Jordan also mentioned other A-listers, telling the crowd, "I stand here because of the people that came before me, Sidney Poitier, Denzel Washington, Halle Berry, Jamie Foxx, Forest Whitaker, Will Smith. To be amongst those giants, amongst those great, greats, amongst my ancestors, amongst my guys. Thank you, everybody in this room and everybody at home for supporting me over my career. I feel it. I know you guys want me to do well, and I want to do that because you guys bet on me."

"So thank you for keeping betting on me, I'm gonna keep stepping up, keep being the best version of myself I can be. So I just want to say thank you to everybody in this room that had something to do with my success. I love you guys," he continued.

Jessie Buckley made history as the first Irish winner of Best Actress award at the Oscars 2026 for her performance in Hamnet.

In her acceptance speech, she thanked her family, fans, fellow nominees and everyone involved with the flick.

"It's Mother's Day in the U.K. today, so I would like to dedicate this to the beautiful chaos of a mother's heart," she continued.

The Oscars 2026 also had a somber moment when Billy Crystal introduced a celebration honoring Rob Reiner.

"I met Mr. Rob Reiner when I was cast as his best friend in an episode of All in the Family and it went so well that Rob said, 'It was fun playing your best friend. Why don't we keep it going?' And it was a thrill to see him evolve from a great comic actor to a master storyteller," he began.

Crystal gave an overview of Reiner's career, adding, "My friend Rob's movies will last for lifetimes because they were about what makes us laugh and cry and what we aspire to be: Far better in his eyes, far kinder, far funnier, and far more human… to the millions who have enjoyed his films all these years, I want you to know here and around the world, how many times Rob told me that it meant everything to him that his work meant something to you. And for us who had the privilege of working with and knowing him and loving him, all we can say is, buddy, what fun we had storming the castle."

Some of Reiner's former costars later went on stage and stood behind Crystal, including Meg Ryan, Annette Bening, Kathy Bates, Cary Elwes, Christopher Guest, Michael McKean, Demi Moore, Jerry O'Connell, Mandy Patinkin, Fred Savage and Kiefer Sutherland.

The Oscars 2026 also remembered the stars Hollywood lost over the past year — including Robert Redford and Diane Keaton — as the theme from The Princess Bride played in the background.