Kieran Culkin has won his first Oscar for Best Supporting Actor at the 97th Academy Awards. This is Culkin’s first-ever Oscar nomination and first win. Culkin won the Oscar for his role in Jesse Eisenberg’s “A Real Pain,

Kieran Culkin ended this awards season at Sunday's Oscars the way he began it — with an outrageous speech — but this time with a hilarious callback to a bet with his wife. Culkin, who won Best Actor in a Supporting Role for his part as the mourning Benji in A Real Pain,

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

Kieran Culkin's wife, Jazz Charton, looked uncomfortable during Culkin's Oscar acceptance, a body language expert noticed.

Macaulay Culkin celebrated his brother Kieran Culkin's win at the 97th Academy Awards for his supporting role in Jesse Eisenberg's A Real Pain. When speaking at the Vanity Fair Oscars party on the red carpet,

Kieran Culkin has won the Academy Award for Best Supporting Actor at the 2025 Oscars.The actor dedicated the latter half of his acceptance speech to his wife, telling a story about how she told him they could have four kids "if he wins an Oscar.

Home Alone star Macaulay Culkin could not hold back his tears as his brother, Kieran Culkin, won the Best Supporting Actor award at the 97th edition of the Oscar Awards for his role of Benji in A Real Pain.

Though Kieran Culkin won Best Supporting Actor for A Real Pain at the 2025 Oscars, he originally tried backing out of the film.

Kieran Culkin is taking home his first Oscar for his performance in the Jesse Eisenberg film “ A Real Pain .” Culkin, who was a favorite to win best supporting actor heading into the 97th Academy Awards Sunday, has consistently won accolades for the role throughout awards season.

LOS ANGELES (AP) — Kieran Culkin won the Oscar for best supporting actor Sunday at the 97th Academy Awards, completing a sweep of the category that followed his dominance in television awards last season. The award, for portraying the chaotic but endearing Benji in Jesse Eisenberg’s “A Real Pain,” marked his first win and nomination.

LOS ANGELES (Reuters) - Kieran Culkin won the best supporting actor Oscar on Sunday ... Culkin told New York magazine last year he got cold feet about playing Benji in "A Real Pain," until Emma Stone, a producer on the film and his former girlfriend ...