Hollywood Celebrates a Night Where Records Were Made Without Sean Penn’s Help

The 98th Academy Awards were a night for celebrating records, and the most notable one belonged to a man who wasn’t there to celebrate it. Sean Penn won Best Supporting Actor for One Battle After Another, his third career Oscar and a result that ties the all-time male acting record held jointly by Jack Nicholson, Walter Brennan, and Daniel Day-Lewis. Presenter Kieran Culkin stepped in with dry humor to collect the award in Penn’s absence, and the crowd responded with warm appreciation.

Penn’s three Oscars span more than 20 years and two categories. He won Best Actor for Mystic River in 2004 and Milk in 2009, and now Best Supporting Actor for his performance as a militaristic, ideologically driven officer in Paul Thomas Anderson’s acclaimed film. That span of time and diversity of roles makes Penn’s achievement all the more remarkable in the context of Oscar history.

Anderson had a brilliant night of his own. He won Best Adapted Screenplay and Best Director for One Battle After Another — his first two Oscars in a career defined by critical praise and industry admiration. Anderson’s double win was one of the evening’s most celebrated moments, drawing sustained applause from the room. The film’s success in multiple categories confirmed its status as the definitive work of the awards season.

Conan O’Brien was a confident and engaging host, using humor and topicality to set a distinctive tone for the evening. His monologue touched on artificial intelligence displacing workers in entertainment and celebrated the diversity of the nominees, who came from 31 countries across six continents. His framing of the ceremony as a global event felt timely and meaningful.

Michael B. Jordan won Best Actor for Sinners, defeating Leonardo DiCaprio. Between Jordan’s victory, Anderson’s historic double, and Penn’s remarkable absent triumph, the 2026 Oscars left the entertainment world with more than enough to discuss for months.