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.

At the 2025 Oscars, Best Supporting Actor winner Kieran Culkin didn't just make another pregnancy pact with wife Jazz Charton. The A Real Pain star also paid tribute to his erstwhile TV sibling Jeremy Strong,

Kieran Culkin won the O in EGOT tonight, scoring the Oscar for Best Supporting Actor for his work in A Real Pain. But even though this was the Academy Awards, we flashed back to the Emmys. It was Culkin’s second time beating his Succession co-star Jeremy Strong,