Kieran Culkin took home the Oscar for Best Supporting Actor at the 2025 Academy Awards for his role as Benji Kaplan in Jesse Eisenberg's A Real Pain.

In A Real Pain, Culkin and Eisenberg play an odd-couple cousin pairing on a trip around their grandmother's native Poland. As the pair navigate their own fraught relationship, they also connect with their family's history and what their grandmother experienced during the Holocaust.

Culkin's Oscar win for A Real Pain marks the end of a dominant awards season run, during which he also took home the BAFTA, the Critics Choice Award, the Golden Globe, and the SAG Award. He beat out fellow nominees Yura Borisov (Anora), Edward Norton (A Complete Unknown), Guy Pearce (The Brutalist), and his Successionco-star Jeremy Strong (The Apprentice).

Culkin opened his Oscar speech by singling out Strong's performance, saying, "By the way, Jeremy, you were amazing in The Apprentice."

After some censored swearing, Culkin added, "I'm not supposed to single anyone out; that's favoritism... but you were great."

But Strong wasn't the only person Culkin shouted out in his speech. In addition to thanking A Real Pain writer and director Jesse Eisenberg, he also told a story about his wife Jazz Charton. During his acceptance speech for Lead Actor in a Drama at the 2024 Emmys, he revealed that Charton had said they would have a third child if Culkin won the Emmy.

"Turns out, she said that because she didn't think I was going to win," he joked.

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But that Emmys request wasn't the end of the saga. Culkin revealed that after the Emmys, he told Charton he really wanted four kids. Her response? "'I will give you four when you win an Oscar,'" Culkin recalled.

He concluded: "Jazz, love of my life, ye of little faith, 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?"