History Made at the 98th Oscars as Sean Penn Claims Third Award

The 98th Academy Awards produced a historic result when Sean Penn won the Best Supporting Actor award for his performance in One Battle After Another, a Paul Thomas Anderson film that proved to be the night’s dominant work. The win gave Penn his third career Oscar, tying him with Jack Nicholson, Walter Brennan, and Daniel Day-Lewis for the most acting wins by any male performer in the history of the ceremony. Penn, however, was not present at the Dolby Theatre.
Presenter Kieran Culkin, who had won the same award the previous year, collected the trophy and offered a good-humored explanation for Penn’s absence. Whether Penn’s decision to skip echoed Eminem’s famous absence from his own Oscar win years earlier — when the rapper reportedly stayed home to watch with his daughter — is unknown. Penn’s reasons for not attending were not disclosed.
His performance in One Battle After Another as a rigidly obsessive military figure earned near-universal critical praise. Paul Thomas Anderson’s direction and screenplay also drew acclaim, resulting in wins for both Best Director and Best Adapted Screenplay. For Anderson, who had been a perennial awards season presence without a win for decades, the recognition was enormously meaningful.
Host Conan O’Brien opened proceedings with a blend of topical humor and sincere reflection. He joked about artificial intelligence rendering human hosts obsolete, a comment that landed with particular resonance among the Hollywood crowd. He also spoke movingly about the global reach of cinema, noting the record 31 countries represented among the nominees.
Michael B. Jordan took home Best Actor for his performance as twins in Sinners, edging out Leonardo DiCaprio in one of the most competitive races in years. It was a night defined by its historical weight — with Penn’s third Oscar win sitting at the very center.