Three-Time Oscar Winner Sean Penn Skips Ceremony, Makes History Anyway

The 98th Academy Awards produced one of its most talked-about moments not because of a speech, but because of a silence — the silence left by Sean Penn’s empty seat. Penn won the Best Supporting Actor award for One Battle After Another but was nowhere to be found at the Dolby Theatre when his name was announced. Presenter Kieran Culkin handled the moment with humor, joking that Penn either couldn’t make it or simply chose not to, before accepting the award on his behalf.

Sean Penn’s three Oscar wins now place him in exclusive company. He joins Jack Nicholson, Walter Brennan, and Daniel Day-Lewis as the only male actors in history to win three Academy Awards for acting. His previous Best Actor wins came for Mystic River in 2004 and Milk in 2009, and this latest recognition underscores his remarkable consistency across decades of work.

In One Battle After Another, Penn portrayed a military officer consumed by obsession — a character that required both physical intensity and psychological depth. Director Paul Thomas Anderson, who helmed the film, had a landmark night of his own, picking up Oscars for both Adapted Screenplay and Best Director. It was a long-awaited breakthrough for Anderson, whose films have long been celebrated by critics.

Host Conan O’Brien kicked off the evening with sharp humor, joking about the rise of artificial intelligence and his uncertain status as a “human host.” He acknowledged a world full of tension but urged the audience to find hope in cinema’s power to unite people across borders. Nominees from 31 countries and six continents reflected the increasingly global nature of modern filmmaking.

The night’s other major storyline was Michael B. Jordan’s Best Actor win for Sinners, in which he played twins — a performance that edged out Leonardo DiCaprio. Between Penn’s record, Anderson’s long-overdue recognition, and Jordan’s triumph, the 2026 Oscars delivered a night full of talking points.