Kieran Culkin wins first Oscar for ‘A Real Pain’ at the 2025 Academy Awards

Kieran Culkin took home the Best Supporting Actor award at the 97th Academy Awards. The win, for his performance as the multifaceted Benji in Jesse Eisenberg's A Real Pain, sealed his reign in the category, after a series of wins on television.

Kieran Culkin wins his first Oscar for ‘A Real Pain’

Oscar victory is the first nomination and win for Kieran Culkin, proving that his masterful performance in A Real Pain merits all the acclaim. His long path to achieving this height took him decades ago with his iconic performance in Igby Goes Down. Nevertheless, his character Roman Roy, the broodingly funny role in HBO's Succession, earned him worldwide fame and was awarded numerous trophies, including Golden Globe, Emmy, and Screen Actors Guild Awards.

Kieran Culkin’s Zegna style

For his Academy Awards night, Kieran Culkin wore a bespoke Zegna tuxedo, a bold deviation from the norm of black. The rich green shawl collar jacket, with its accompanying classic black tuxedo shirt, bow tie, and trousers, epitomized a combination of refinement and contemporary panache. Culkin's refined outfit perfectly matched his victorious moment on Hollywood's biggest stage.