The Actor Who Collected Sean Penn’s Oscar Wasn’t Sean Penn

Viewers and attendees of the 98th Academy Awards were treated to an unusual spectacle when Best Supporting Actor was announced and Sean Penn did not appear. Penn, who won for One Battle After Another, was absent from the Dolby Theatre, leaving presenter Kieran Culkin to accept the Oscar in his stead. Culkin’s casual delivery of the line that Penn either couldn’t or didn’t want to attend the ceremony was the most memorable quip of a well-executed evening.
For Penn, the award was his third Oscar — a number that places him in the company of Jack Nicholson, Walter Brennan, and Daniel Day-Lewis, the only other male actors who have reached that total. Penn previously won Best Actor in 2004 for Mystic River and in 2009 for Milk. The fact that his third win came in the supporting category adds an interesting twist to his place in Oscar history.
Penn’s role in One Battle After Another was that of a military officer consumed by ideology, a character that critics found both chilling and compelling. The film also gave Paul Thomas Anderson his first Oscar wins — he claimed both Best Adapted Screenplay and Best Director — after a career’s worth of critical acclaim and awards season recognition without the ultimate prize. Anderson’s double win was one of the warmest moments of the evening.
Conan O’Brien hosted the ceremony and delivered a polished, funny, and occasionally moving performance. His opening joke about being the “last human host” before AI takes over was prescient and well-received. He went on to emphasize the global nature of the nominees, representing 31 countries, as a sign of hope and shared humanity.
Michael B. Jordan’s Best Actor win for Sinners came at the expense of Leonardo DiCaprio, marking one of the bigger surprises of the evening. Between Sean Penn’s no-show and Jordan’s victory, the 2026 Oscars kept audiences guessing from beginning to end.