Film history has its share of peculiar Oscar moments, and the 98th Academy Awards delivered one of the most distinctive: Sean Penn won Best Supporting Actor for One Battle After Another — his third career Oscar and a record-tying achievement — and wasn’t there to receive it. Presenter Kieran Culkin stepped to the microphone, cracked a joke, and accepted the trophy on Penn’s behalf. The audience laughed, applauded, and the evening moved on, though Penn’s missing presence hung over the rest of the night.
Penn now stands beside Jack Nicholson, Walter Brennan, and Daniel Day-Lewis as one of only four men in Academy history to have won three acting Oscars. His previous wins — for Mystic River in 2004 and Milk in 2009 — were both in the lead actor category, making his latest supporting win a surprising and meaningful addition. Over two decades of celebrated work, Penn has demonstrated a commitment to his craft that the Academy has now recognized three times.
His performance in One Battle After Another, as a military officer whose dogmatic certainty leads him to ruin, was praised as one of the most powerful of his career. Paul Thomas Anderson, who wrote and directed the film, had a career-high night himself, claiming his first two Oscars — for Best Adapted Screenplay and Best Director. The film’s success dominated the evening in a way few productions do.
Conan O’Brien was a well-received host, offering sharp humor about AI disrupting the entertainment industry alongside a genuine celebration of the ceremony’s international character. Nominees from 31 countries on six continents made the 98th Oscars one of the most diverse in recent history, and O’Brien acknowledged that with evident pride. His hosting struck the right balance between entertainment and substance.
Michael B. Jordan won Best Actor for Sinners, beating a widely favored Leonardo DiCaprio. The 2026 Oscars gave audiences records, upsets, and an unforgettable void — the empty stage where one of cinema’s greatest was supposed to stand.
The 2026 Oscars Will Be Remembered for Sean Penn’s Absence as Much as His Achievement
