The 2026 Academy Awards gifted Hollywood one of its more unusual moments when Sean Penn, named Best Supporting Actor for One Battle After Another, was simply not there. The Dolby Theatre audience sat in brief silence before Kieran Culkin, who had won the same award the prior year, stepped to the microphone and accepted on Penn’s behalf. Culkin’s humor diffused any awkwardness, though Penn’s absence remained the talking point of the night.
Penn’s victory gave him his third acting Oscar, placing him on equal footing with Jack Nicholson, Walter Brennan, and Daniel Day-Lewis. Those four men form a unique class in the history of the Academy Awards, having each accumulated three acting wins — a total no male actor has ever surpassed. Penn’s wins now span both the lead and supporting categories, adding further distinction to his achievement.
His role in One Battle After Another as an obsessive military officer drew immense critical praise throughout the awards season. Paul Thomas Anderson, who directed the film, matched Penn’s success by winning both Adapted Screenplay and Best Director. For Anderson, the double win represented a first in a career that had already produced some of the most admired American films of the past three decades.
Conan O’Brien hosted the ceremony and navigated it with charm and wit. His comments about AI posing a threat to human hosts gave the evening a topical edge, while his acknowledgment of the ceremony’s international reach — nominees from 31 countries — set a tone of global inclusivity. The evening was one of the more thoughtfully constructed Oscar ceremonies in recent years.
Michael B. Jordan took Best Actor for Sinners, beating Leonardo DiCaprio in one of the night’s most anticipated races. Between Jordan’s win, Anderson’s double, and Penn’s record-tying but oddly absent triumph, the 98th Oscars delivered a night that will be discussed for years.
