Photo by Harald Krichel / Wikimedia Commons (CC BY-SA 3.0)
19
Conventional Oscar winners walk to the stage, thank their directors, cry, and sit back down. Sean Penn has never been a conventional Oscar winner, and the 98th Academy Awards made that absolutely clear. Penn won Best Supporting Actor for One Battle After Another — his third career Oscar, tying the record for most acting wins by a male performer — and was not at the Dolby Theatre to receive it. Kieran Culkin accepted on his behalf with a quip that became the most-quoted line of the evening.
Penn’s place in Oscar history is now permanent and extraordinary. Three wins place him alongside Jack Nicholson, Walter Brennan, and Daniel Day-Lewis — each of whom spent their careers building toward that milestone. Penn reached it in typical fashion: on his own terms, from somewhere else. His previous wins were for Best Actor in Mystic River and Milk — two of the most praised performances of their respective years.
His performance in One Battle After Another, as a militaristic officer undone by his own beliefs, was universally celebrated by critics as one of the performances of the year. Director Paul Thomas Anderson earned his first-ever Oscars on the same night, winning Best Adapted Screenplay and Best Director and cementing a night of double achievement for the film. Anderson’s recognition drew an emotional response from the audience.
Host Conan O’Brien delivered a witty and warm performance, opening with a comment about artificial intelligence threatening his own role before celebrating the unprecedented international makeup of the nominees. With participants from 31 countries on six continents, the 98th Oscars were a genuinely global event. O’Brien acknowledged that with evident pride.
Michael B. Jordan’s Best Actor win for Sinners over Leonardo DiCaprio added another layer of drama to an already packed evening. The 2026 Oscars were a night of records, firsts, and one memorably missing legend.
