Oscars 2026: Sean Penn makes history and ties all-time record for most acting wins
With his ‘Best Supporting Actor’ Oscar win for One Battle After Another, Sean Penn has made Academy history and tied the record for most wins by a male actor.
He may not have been in attendance to pick up his trophy, but Sean Penn has earned the distinction of becoming a three-time Academy Award winner. This ties the record that is also held by Walter Brennan, Jack Nicholson, and Daniel Day-Lewis.
Penn won for his terrifying performance as Colonel Lockjaw in One Battle After Another, which was his first nomination in the ‘Best Supporting Actor’ category. He was previously nominated for ‘Best Actor’ in Dead Man Walking, Sweet and Lowdown, and I Am Sam before winning twice for Mystic River and Milk.
Penn’s path back to the Oscars has been an interesting one, as early critical prizes were split between different performances; Stellan Skarsgård won the Golden Globe for Sentimental Value, Jacob Elordi won the Critics’ Choice for Frankenstein, and the National Board of Review awarded Penn’s co-star, Benicio del Toro.
Penn’s victory was clinched after he won both the Bafta and the Actor Awards for ‘Best Supporting Actor’. Amusingly, the only ceremony that Penn showed up to was the Golden Globes, where he was seen smoking in the room.
Penn’s Oscar trajectory is similar to that of Jack Nicholson, who had two lead actor victories (for One Flew Over The Cuckoo’s Nest and As Good As It Gets) and one for supporting in Terms of Endearment. Day-Lewis has three wins for ‘Best Actor’ for My Left Foot, There Will Be Blood, and Lincoln, and Brennan had three for ‘Best Supporting Actor’ for Come and Get It, Kentucky, and The Westerner.
The all-time record for most Oscar wins by any performer is Katherine Hepburn, who has four Best Actress wins for Morning Glory, Guess Who’s Coming to Dinner, The Lion in Winter, and On Golden Ponds. Actresses with three wins include Meryl Streep, Glenn Close, and Ingrid Bergman.
Whether this record could be tied once more is an interesting question. Living male actors with two wins include Robert De Niro, Denzel Washington, Adrien Brody, Mahershala Ali, Dustin Hoffman, Kevin Spacey, Tom Hanks, Anthony Hopkins, Michael Caine, and Christoph Waltz.
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