Macaulay Culkin ‘Cried’ Over Brother Kieran’s Oscar Win and Only Watched His Category: ‘There Was No Way He Was Not Going to Win’

Macaulay Culkin revealed at the Vanity Fair Oscars party (via Entertainment Weekly) that he cried when his younger brother Kieran Culkin won the Oscar for best supporting actor at the 2025 Academy Awards. It turns out that category was the only part of the Oscars telecast that Macaulay Culkin and his partner, fellow actor Brenda Song, watched.

“Just the Best Supporting Actor,” Macaulay Culkin said when asked if he watched the show. “That’s the only thing I watched. True story, true story… I cried. And I was like, ‘I’m gonna see you later.’”

Kieran Culkin won the Oscar for best supporting actor thanks to his acclaimed performance in Jesse Eisenberg’s “A Real Pain.” He was nominated opposite Yura Borisov (“Anora”), Edward Norton (“A Complete Unknown”) and Guy Pearce (“The Brutalist”). Culkin was considered the Oscar frontrunner after sweeping awards season with supporting actor wins at the Golden Globes, Critics’ Choice Awards, SAG Awards and BAFTAs.

When asked if they expected Kieran Culkin to win the Oscar, Song answered: “Of course. Let’s be real. We’re allowed to say that.”

“Yeah, absolutely,” Macaulay Culkin said. “He was front row, aisle, closest to the stairs. There was no way he was not going to win.”

Macaulay and Kieran Culkin both got their starts as child actors and appeared together in films such as “Home Alone.” Kieran Culkin showed his family love during his Oscars acceptance speech, most notably when he brought up the infamous moment when, after winning the 2024 Emmy Award for best actor for HBO’s “Succession,” he asked his wife, Jazz Charton, to have a third child — which he did only because she’d promised to have another kid if he won the Emmy, not thinking he would.

“After the show, we’re walking through a parking lot … and she goes, ‘Oh, God, I did say that!’” Kieran Culkin said. “‘I guess I owe you a third kid.’ And I turned to her, and I said, ‘Really, I want four.’ She turned to me — I swear to God, this happened there’s just over a year ago — she said, ‘I will give you four when you win an Oscar.’”

In the audience, Charton acknowledged that she had, indeed, made that promise. “And I have not brought it up once until just now,” Kieran Culkin continued. “I just have this to say to you, 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.”