Sean Penn Doesn’t Show, But That Doesn’t Stop Him From Making Oscar History

In a night full of memorable Oscar moments, the most talked-about may have been a simple announcement followed by silence. Sean Penn’s name was read out as the Best Supporting Actor winner for One Battle After Another, and nobody walked to the stage at the Dolby Theatre. Presenter Kieran Culkin accepted with humor, and Penn — who has a known habit of skipping award shows — was declared the night’s most unexpectedly absent champion.
The win gave Penn his third career Oscar, matching the record of Jack Nicholson, Walter Brennan, and Daniel Day-Lewis as the most decorated male acting performers in Academy history. His two previous wins came as Best Actor for Mystic River in 2004 and Milk in 2009. The shift to Best Supporting Actor for his latest win is a reflection of Penn’s willingness to take on complex roles that serve the story, not the star.
One Battle After Another, the film behind Penn’s third win, is a darkly comic and tonally unique Paul Thomas Anderson thriller. Penn plays a military officer who becomes consumed by his rigid worldview — a character that critics widely praised for its intensity and nuance. Anderson’s film swept key awards, with Anderson himself winning both Adapted Screenplay and Best Director — his first Oscars after a career of revered but previously unrewarded filmmaking.
Conan O’Brien hosted the ceremony with his characteristic mix of comedy and warmth. His opening monologue addressed artificial intelligence as an existential concern for the entertainment industry. He also took time to highlight the unprecedented global diversity of the nominees, drawn from 31 countries, framing the Oscars as a celebration that belongs to the world.
Michael B. Jordan delivered one of the night’s bigger surprises, beating Leonardo DiCaprio for Best Actor in Sinners. Between Penn’s absent triumph and Jordan’s unexpected win, the 98th Oscars gave audiences plenty to discuss long after the credits rolled.