Sean Penn has never been one to follow Hollywood’s unwritten rules, and the 2026 Academy Awards offered perhaps the most vivid illustration of that truth. The actor won Best Supporting Actor for One Battle After Another at the 98th Oscars, tying the record for the most acting wins by a male performer in Academy history — and he did it without being in the room. Presenter Kieran Culkin handled the unprecedented moment with good humor.
Penn’s three Oscars tie him with Jack Nicholson, Walter Brennan, and Daniel Day-Lewis — an elite group that represents the very pinnacle of acting achievement in Hollywood. His previous two wins, for Mystic River in 2004 and Milk in 2009, both came in the Best Actor category. This latest honor, for a supporting role in a darkly comic Paul Thomas Anderson film, adds a new dimension to an already extraordinary career.
In One Battle After Another, Penn plays a military officer so consumed by his principles that they ultimately devour him. The performance has been widely described as some of Penn’s finest work, balancing physical intensity with psychological intricacy. The film also made history for director Paul Thomas Anderson, who walked away with his first two Oscars for Adapted Screenplay and Best Director after more than two decades of acclaimed filmmaking.
Host Conan O’Brien opened the ceremony with a monologue that was both funny and strangely poignant. He joked about being “the last human host” in an age of AI disruption, and urged the audience to find beauty and meaning in a world full of uncertainty. He also celebrated the global scope of the nominees, who represented 31 countries and six continents.
Michael B. Jordan beat Leonardo DiCaprio for Best Actor, winning for his dual performance in Sinners. The evening was rich in headline moments, but none quite as distinctive as the one that unfolded when Sean Penn’s name was called and the stage remained empty.