Hollywood history was quietly rewritten at the 98th Academy Awards when Sean Penn received his third acting Oscar for Best Supporting Actor in One Battle After Another. Penn’s win ties him with Jack Nicholson, Walter Brennan, and Daniel Day-Lewis as the only men ever to achieve three acting wins at the Academy Awards. The actor himself was absent from the Dolby Theatre, and presenter Kieran Culkin accepted on his behalf with characteristic dry humor.
Penn’s Oscar journey began with Best Actor wins for Mystic River in 2004 and Milk in 2009. Two decades of world-class work later, his third win — this time in a supporting role — reflects both his versatility and his ongoing commitment to complex, demanding performances. Those who have followed his career know that his absence from the Oscars ceremony says nothing about his dedication to his craft.
The film behind his third win, One Battle After Another, was Paul Thomas Anderson’s first major commercial and awards success as a directing and writing double winner. Anderson claimed both Best Adapted Screenplay and Best Director on the same night — his first Academy Awards after a celebrated career stretching back to the 1990s. Penn’s role as an obsessive, dogmatic military officer gave the film its most magnetic presence.
Conan O’Brien hosted the evening with a smart and self-aware monologue that opened proceedings on a note of optimistic anxiety. His joke about AI rendering human hosts obsolete was topical and well-landed. He also drew attention to the global composition of the nominees, who hailed from 31 countries, calling the Oscars an increasingly international event.
Michael B. Jordan claimed Best Actor for Sinners, surprising many who had anticipated Leonardo DiCaprio’s victory. The 2026 Oscars delivered one historic moment after another — with Sean Penn’s absent triumph at the very center of the evening.
