After dominating the Best Supporting Actor category throughout the awards season, Kieran Culkin capped off his incredible run Sunday night by taking home the Oscar for Best Supporting Actor at the 2025 Academy Awards. His victory came as little surprise, following previous wins at the Golden Globes, SAG Awards, and other major ceremonies.

But while his award was expected, his acceptance speech stole the show—especially when he made a playful plea to his wife for a fourth child.

"Let's Get Cracking on Those Kids"

Accepting the award from last year's Best Supporting Actor winner Robert Downey Jr., Culkin expressed gratitude to several people, including Jesse Eisenberg, who directed him in the winning role for "A Real Pain."

"Thank you for this movie, you're a genius," Culkin said. "I will never say it to your face, so soak it up."

He then reflected on a moment from last year's Emmy Awards, when he publicly asked his wife, Jazz Charton, for a third child.

"About a year ago, I was on stage and I very stupidly asked her for a third kid," Culkin recalled. "Turns out she said that because she thought I wouldn't win."

But this time, Culkin revealed that his wife had set the stakes even higher.

"So we are walking through the parking lot looking for our car, and she goes, 'Oh god, I did say that. I guess I owe you a third kid.' And I turned to her and said, 'Really, I want four.'"

Her response? A challenge.

"She turned to me and said, 'I will give you four... when you win an Oscar.'"

With his Academy Award now in hand, Culkin made sure to remind her of their agreement on live television.

"No pressure, I love you, I'm really sorry I did this again," he quipped. "And let's get cracking on those kids—what do you say?"

Culkin's Career High

Culkin's Oscar-winning performance came in a category stacked with talent, including Guy Pearce (The Brutalist), Yuriy Borisov (Anora), Edward Norton (A Complete Unknown), and Jeremy Strong (The Apprentice). His win solidifies his rise from an acclaimed television actor—having won an Emmy last year for HBO's Succession—to an Oscar-winning movie star.

As he basks in his career-defining moment, one question remains: Will baby No. 4 be on the way?