Oscars 2026: Sean Penn’s Historic Win Comes With an Unexpected Twist

Sunday night’s 98th Academy Awards will be remembered not only for what happened on stage, but for what didn’t. Sean Penn, the acclaimed actor known for his gripping performances and his aversion to award ceremonies, won Best Supporting Actor for One Battle After Another — and then failed to appear. Presenter Kieran Culkin filled the void with a characteristically dry remark before collecting the Oscar on Penn’s behalf. The Dolby Theatre audience responded with laughter and sustained applause.

Penn’s victory gave him his third Oscar, tying him with Jack Nicholson, Walter Brennan, and Daniel Day-Lewis for the most acting Oscars ever awarded to a man. His prior wins — Best Actor for Mystic River and Milk — had already made him one of the most celebrated performers in screen history. The third win, in a supporting capacity, only deepens an already staggering career record.

In One Battle After Another, Penn’s portrayal of a militaristic officer trapped by his own rigid beliefs was called one of the performances of the year. Director Paul Thomas Anderson matched that standard, winning both Best Adapted Screenplay and Best Director — his first-ever Oscars — in a night that confirmed his status as one of the greats of his generation. Anderson’s work on the film earned the highest possible recognition from the Academy.

Conan O’Brien was a well-calibrated host, blending humor with reflection as he guided the ceremony. His opening remarks took aim at artificial intelligence while also celebrating the global diversity of the nominees. With 31 countries represented across the nominees, O’Brien framed the evening as a reminder that cinema belongs to the world.

Michael B. Jordan’s Best Actor win for Sinners over Leonardo DiCaprio was among the most eagerly anticipated results of the evening. The 2026 Oscars closed as one of the more historically rich ceremonies in recent years.