During the Oscars 2025 ceremony in Los Angeles on Sunday, March 2, the A Real Pain star accepted the Best Supporting Actor statuette from presenter Robert Downey Jr.
"Oh, my God, that's crazy. I don't even know. Mr. Downey, sir, thanks for handing this to me," Culkin, 42, said at the start of his acceptance speech, after taking the stage at the Dolby Theatre. "This means a lot coming from you."
After thanking A Real Pain director Jesse Eisenberg and his family, he went on to give a special shoutout to his wife.
"I love you Jazz," he said. "I have to thank my wife Jazz for absolutely everything, for giving me my favorite people in the world."
"Please don't play the music because I want to tell a really quick story about Jazz. About a year ago, I was on a stage like this, and I very stupidly publicly said that I want a third kid from her, because she said, If I won the award, she would give me the kid," he continued, referring to his the 2023 Emmy Awards acceptance speech.
"It turns out she said that because she didn't think I was gonna win," he teased. "People came up to her and were like really annoying her. I think it got to her. But anyway, after the show, we're walking through a parking lot. She's holding the Emmy. We're trying to find our car. Emily, you were there so you're a witness, and she goes, 'Oh, God, I did say that. I guess I owe you a third kid.' And I turned to her, and I said, 'Really, I want four.'"
"And she turned to me, I swear to God, this happened. It was just over a year ago. She said, 'I will give you four when you win an Oscar.'"
"I held my hand out. She took it, and I have not brought it up once, until just now," he concluded. "You remember that, honey, you do? Okay, then I just have this to say to you, Jazz, love of my life...No pressure. I love you. I'm really sorry I did this again, and let's get cracking on those kids. What do you say?"
Also nominated in the Academy's best supporting actor category this year were Yura Borisov for Anora, Edward Norton for A Complete Unknown, Guy Pearce for The Brutalist and Jeremy Strong for The Apprentice.
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In A Real Pain, Culkin and Jesse Eisenberg star as polar-opposite cousins who reunite for a tour through Poland to honor their grandmother. The dramedy was also written and directed by Eisenberg, 41.
Borisov a classically trained Moscow-born actor, plays henchman Igor, who grows close to Anora throughout the film. Baker wrote the role for Borisov, 32, after seeing him at the Cannes Film Festival in 2021 in the award-winning film Compartment No. 6.
Pearce's role in the historic drama earned him his first Oscar nomination and landed multiple nods this awards season, including at the BAFTAs and Golden Globes.
Culkin's former Succession costar Strong, 46, stars in The Apprentice as attorney Roy Cohn, the real-life mentor of Donald Trump (Sebastian Stan).
The movie follows a young Trump, now 78, during the early days of his career in the '70s and '80s as he builds his real-estate business in New York City.
Stan, 42, is also nominated for Best Actor at the Oscars this year.