Sean Penn Is Now in the Same Sentence as Jack Nicholson, Walter Brennan, and Daniel Day-Lewis

The sentence now reads: “Jack Nicholson, Walter Brennan, Daniel Day-Lewis, and Sean Penn are the only male actors in history to win three acting Oscars.” Penn joined that sentence at the 98th Academy Awards, winning Best Supporting Actor for One Battle After Another to claim his third career Oscar. He was not at the Dolby Theatre to mark the occasion, but Kieran Culkin stepped in to accept the award and offer a pointed joke about the winner’s apparent disinterest in attending his own historic moment.

Penn’s prior wins — Best Actor for Mystic River in 2004 and Milk in 2009 — were each recognized at the time as extraordinary achievements. His third win, for a supporting performance in a Paul Thomas Anderson thriller, adds depth to a career that has never sought the obvious path. Penn’s role in One Battle After Another as a militaristic officer driven by his own extremism was praised universally as one of the finest performances of the year.

Paul Thomas Anderson had a career-high night, winning both Best Adapted Screenplay and Best Director — his first Oscars after decades of acclaimed filmmaking. The industry’s response to Anderson’s wins was one of sustained, warm celebration, reflecting the deep admiration that has long surrounded his work. The film’s success across multiple categories confirmed it as the dominant artistic statement of the awards season.

Host Conan O’Brien was entertaining, topical, and genuinely warm throughout the ceremony. He opened with a joke about being the last human host before artificial intelligence takes over and spent meaningful time celebrating the global diversity of the nominees — from 31 countries and six continents. His hosting struck the right tone from start to finish.

Michael B. Jordan won Best Actor for Sinners, defeating a favored Leonardo DiCaprio. The 2026 Oscars added a fourth name to one of cinema’s most exclusive lists — and all four of those names are now permanently linked in the history of the Academy Awards.