Why Sean Penn Skipping the Oscars May Be the Most On-Brand Moment of His Career

Sean Penn has always done things his own way. So when the 98th Academy Awards announced him as the Best Supporting Actor winner for One Battle After Another, and the stage remained empty, it felt strangely fitting. Penn’s absence from the Dolby Theatre was explained — or rather, unexplained — by presenter Kieran Culkin, who quipped that Penn either couldn’t make it or simply didn’t want to, before collecting the award on the absent winner’s behalf.
The win gave Penn a third Oscar, placing him in the exclusive company of Jack Nicholson, Walter Brennan, and Daniel Day-Lewis — the only other male actors in history to have collected three Academy Awards for acting. His previous wins came in the lead actor category for Mystic River in 2004 and Milk in 2009, cementing him as one of the most consistently brilliant screen performers of his generation.
His performance in One Battle After Another as a militaristic officer consumed by ideology was seen by many critics as a career highlight. Director Paul Thomas Anderson, who crafted the film around Penn’s intensity, won his first-ever Oscars for Best Adapted Screenplay and Best Director. The film dominated the ceremony in a manner that few expected heading into the evening, sweeping prestige categories with authority.
Conan O’Brien hosted with familiar wit and a touch of philosophical warmth, opening his monologue with a joke about being “the last human host” of the Oscars before AI renders the role redundant. He celebrated the international diversity of the nominees — drawn from 31 nations across six continents — giving the ceremony a genuinely cosmopolitan feel. His performance as host drew warm reviews.
Michael B. Jordan claimed Best Actor for Sinners, defeating a widely favored Leonardo DiCaprio. The 2026 Oscars gave Hollywood plenty to discuss in the days that followed, with Penn’s absent, record-tying triumph sitting front and center in every conversation.