Kieran Culkin Accepts Oscar on Sean Penn’s Behalf After Actor Skips Ceremony

There was a moment of confusion and laughter at the 2026 Oscars when Sean Penn was announced as the Best Supporting Actor winner and no one came to the stage. Penn, who was not at the Dolby Theatre for the 98th Academy Awards, had his award accepted by presenter Kieran Culkin, who wryly noted that the winner either couldn’t attend or simply chose not to. The crowd quickly warmed to the moment, applauding what was already a historic win.

Penn’s Oscar for his role in One Battle After Another was his third, tying him with Jack Nicholson, Walter Brennan, and Daniel Day-Lewis for the record of most acting awards won by a male performer. All four men have three Oscars each, a number no other male actor has ever reached. Penn’s first two wins were both in the Best Actor category for his powerful performances in Mystic River and Milk.

Paul Thomas Anderson’s One Battle After Another dominated much of the awards conversation. Penn’s role as a dangerously obsessive military officer was praised as a career highlight by many critics. Anderson himself walked away with two Oscars — Adapted Screenplay and Best Director — in what was the crowning achievement of his long and celebrated career.

Conan O’Brien kept the tone light but meaningful as host, weaving humor with heartfelt acknowledgment of the world’s current anxieties. His opener about artificial intelligence threatening his own job as a host drew big laughs. He also emphasized the international nature of the nominees, calling the ceremony a celebration of global storytelling.

Michael B. Jordan was the night’s Best Actor, winning for his performance as twins in Sinners — a result that denied Leonardo DiCaprio the award many had predicted he would win. The 2026 ceremony will be long remembered for its record-tying moment and its strikingly absent honoree.