From the Dolby Theatre to Wherever Penn Was: A Night of Oscar Firsts and Records

It was the kind of night that rarely comes along even in a ceremony with nearly a century of history behind it. At the 98th Academy Awards, Sean Penn won his third Oscar for Best Supporting Actor for One Battle After Another — tying the all-time male acting record — while Paul Thomas Anderson claimed his first two Oscars, and Michael B. Jordan defeated Leonardo DiCaprio for Best Actor. And through it all, Penn himself was not in the building.

Presenter Kieran Culkin accepted the Best Supporting Actor award on Penn’s behalf, offering a slightly tongue-in-cheek observation about Penn’s failure — or refusal — to attend. Penn’s previous wins were both for lead roles: Mystic River in 2004 and Milk in 2009. His third win places him in permanent company with Jack Nicholson, Walter Brennan, and Daniel Day-Lewis.

Penn’s performance in One Battle After Another drew effusive praise from critics throughout the awards cycle. His portrayal of a military officer undone by his own ideological rigidity was described as one of the most riveting turns of the season. Anderson’s wins for Best Adapted Screenplay and Best Director were a natural complement to Penn’s and ended what had been a long Oscar drought for one of American cinema’s most distinctive voices.

Host Conan O’Brien was in sharp form throughout the evening. His opening monologue touched on the displacement of human creatives by AI and included a warm tribute to the global scope of modern filmmaking. O’Brien called the ceremony an occasion for hope as much as for celebration, noting that nominees came from 31 countries and six continents.

Michael B. Jordan’s Best Actor win for Sinners was celebrated widely as a career milestone. For Penn, his third win — made in absentia — added an unconventional but perfect ending to his Oscar story so far.