Who’s our next three-peat champion?
Friday, March 20, 2026 at 5:00PM
And just like that, Sean Penn became the eighth actor to win three Oscars.
With One Battle After Another, Sean Penn became the eighth person in Academy Award history to win a third acting Oscar. He follows Supporting Actor king Walter Brennan, most honored thespian ever Katharine Hepburn, Swedish superstar Ingrid Bergman, New Hollywood enfant terrible Jack Nicholson, nomination queen Meryl Streep, method actor extraordinaire Daniel Day-Lewis, and too-cool-for-school Oscar favorite Frances McDormand. This honor comes after a period when Penn was fairly removed from the awards conversation, regularly panned at Cannes for his directorial work while winning the favor of a few critics for underseen performances like those in Daddio and Asphalt City. Indeed, he seems so uninterested in playing the game that he barely campaigned and didn’t even show up to collect his prize.
Disregarding whether he deserves it or not, Penn’s victory leads me to wonder who’s next? Who is closest to joining this exclusive club? There are currently 19 two-time acting Oscar winners alive, each a different case, with some landing in the “just a matter of time” field, while others are surely “not happening.” Join me as I go over these possibilities…






