Third Time’s a Charm — but Don’t Expect Sean Penn to Be There for It

Winning three Academy Awards would be a dream for virtually any actor in Hollywood — but Sean Penn treated his third win with the same apparent indifference he seems to apply to most award ceremonies. Penn won Best Supporting Actor for One Battle After Another at the 98th Oscars but was not present at the Dolby Theatre. Presenter Kieran Culkin stepped in, accepted the award with humor, and the evening moved on.
Penn’s three Oscars tie him with Jack Nicholson, Walter Brennan, and Daniel Day-Lewis, completing a quartet of actors who represent the pinnacle of Academy recognition for male performers. Penn’s first two wins were as Best Actor — for Mystic River and Milk — and this latest honor in the supporting category extends his legacy in a new direction. No other male actor has matched three Oscar acting wins in the history of the ceremony.
The film that earned Penn his place in that company, One Battle After Another, is a serious and stylistically rich work from Paul Thomas Anderson. Penn’s portrayal of a military officer consumed by extremism was called one of the most compelling of his career. Anderson’s own Oscars for Best Director and Best Adapted Screenplay added to a landmark evening for the production.
Conan O’Brien was a reliable and entertaining host, drawing big laughs with a quip about being the last human to hold his position before artificial intelligence makes it irrelevant. He also gave a thoughtful tribute to the diversity of the nominees, which included participants from 31 countries around the world. His tone was warm throughout, making for a ceremony that felt both relaxed and significant.
Michael B. Jordan’s Best Actor win for Sinners, edging out Leonardo DiCaprio, completed a night full of surprises. Sean Penn’s record — achieved without a single word spoken at the ceremony — may be the most surprising result of all.