Absent but Triumphant: How Sean Penn Tied the Male Oscar Record

It was an Oscar win that raised eyebrows and generated headlines for all the right and wrong reasons. Sean Penn, one of cinema’s most acclaimed performers, won Best Supporting Actor at the 98th Academy Awards for his role in One Battle After Another — but he did not show up. Presenter Kieran Culkin handled the awkward moment gracefully, collecting the award and joking about Penn’s deliberate or accidental absence.

This victory was Penn’s third Academy Award for acting, a feat matched only by Jack Nicholson, Walter Brennan, and Daniel Day-Lewis in all of Oscar history. His two previous wins were for Best Actor — Mystic River in 2004 and Milk in 2009. Moving from leading man to supporting player, Penn demonstrated once again that he is willing to serve the story rather than chase the spotlight.

His performance in One Battle After Another, a sharp and unsettling film from director Paul Thomas Anderson, was widely described as one of the finest of his career. Penn played a military officer whose rigid worldview pushes him toward something close to madness. Anderson rounded out the film’s success by winning both Adapted Screenplay and Best Director, his first Oscar wins after nearly three decades of acclaimed filmmaking.

Host Conan O’Brien opened the ceremony with a mix of warmth and wit, acknowledging that the world felt like a difficult place while urging the audience to celebrate the power of storytelling. His joke about being the “last human host” at the Oscars reflected real fears about artificial intelligence and the future of creative work. Nominees represented 31 countries, reinforcing the global reach of modern cinema.

The evening’s Best Actor award went to Michael B. Jordan, whose dual role in Sinners won him the prize over Leonardo DiCaprio. Penn’s absence aside, the 2026 Oscars proved to be one of the most eventful ceremonies in years.