Did Macaulay Culkin and wife Brenda Song expect Kieran to win for ‘A Real Pain’? “Of course!” said Song. “Come on, let’s be real.”Macaulay Culkin is celebrating his brother Kieran Culkin’s big night at the Oscars.

Kieran Culkin has won best supporting actor at the 97th Academy Awards, completing his awards season sweep of the category.

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.

Kieran Culkin won the Academy Award for best supporting actor for his role as the descendant of a Holocaust survivor who makes a family pilgrimage to Poland in the dramatic comedy of manners “ A Real Pain. ”

Kieran Culkin's wife congratulated her husband on his Oscar and joked about the "baby pacts" Culkin referenced in his Oscars speech on Sunday night.

Making empty baby pacts may seem foolish but it’s clearly been a great motivator,” wrote Jazz Charton on Instagram.

Kieran Culkin's wife Jazz Charton may have found the motivation behind his award season winning streak. On Tuesday, March 4, Charton shared several pictures from the 97th Academy Awards, and in the caption,

Macaulay Culkin shared his reaction to his brother Kieran Culkin's Oscar win during the Vanity Fair Oscar Party livestream.

Kieran Culkin might shocked viewers when he told the whole world at the Oscars that he wanted to have two more kids, but his wife Jazz Charton doesn't seem too phased by his public request. In fact, Jazz reacted to Kieran's Oscar speech on Instagram, joking that these “empty baby pacts” were actually motivational tools all along.

Macaulay Culkin revealed he got emotional watching his little brother Kieran Culkin win Best Supporting Actor at the Oscars. “I cried,” he told Queer Eye fashion expert Tan France, who interviewed him and his partner,