Sean Penn’s Third Oscar Is a Study in Contradiction — Brilliant, Historic, and Absent

Some Oscar moments are contradictions, and Sean Penn’s third win at the 98th Academy Awards is among the most vivid examples. Penn won Best Supporting Actor for his role in One Battle After Another, recording his third career Oscar and tying the record for male acting wins in Academy history — and then chose not to be present. Kieran Culkin accepted on his behalf, offering a memorable one-liner about Penn’s non-attendance.
The three actors Penn now matches — Jack Nicholson, Walter Brennan, and Daniel Day-Lewis — each went to the ceremony when they won. Penn’s absence was a reminder that he has always operated outside Hollywood’s conventional frameworks. His two previous wins were both attended: Best Actor for Mystic River in 2004 and Milk in 2009. This time, for whatever reason, the Dolby Theatre was not his scene.
Penn’s work in One Battle After Another was the subject of widespread critical admiration. Playing a military officer whose beliefs push him into extremism, Penn brought what many called terrifying clarity to the role. Paul Thomas Anderson’s film swept key categories, with Anderson winning both Best Adapted Screenplay and Best Director — his first Oscars after a career that many had long felt deserved the Academy’s highest recognition.
Host Conan O’Brien brought wit and substance to his role, using his opening monologue to address concerns about artificial intelligence in the entertainment industry and to celebrate the ceremony’s multinational nominee pool. He described nominees from 31 countries across six continents as a testament to cinema’s universal language. His tone was consistently warm and engaging throughout.
Michael B. Jordan defeated Leonardo DiCaprio in the Best Actor category for Sinners. It was a night in which records were tied, careers were crowned, and one of the most acclaimed actors in the world watched it all from somewhere else.