An Oscar Night to Remember — Especially for the Man Who Wasn’t There

The 98th Academy Awards was built for Sean Penn’s attendance — he won, after all, his third Oscar and tied the record for most acting wins by a male performer in history. But Penn wasn’t there, and in his absence, an already remarkable evening became a genuinely unforgettable one. Presenter Kieran Culkin collected the Best Supporting Actor trophy for One Battle After Another and offered a wry line that the crowd found both funny and fitting.

Penn’s place in Oscar history is now cemented alongside Jack Nicholson, Walter Brennan, and Daniel Day-Lewis. His three wins — for Mystic River, Milk, and One Battle After Another — span different roles, different genres, and different decades, making his achievement all the more remarkable. Penn has never been an actor who performs for the camera; he performs for the story.

One Battle After Another, the film that earned Penn his latest honor, is a darkly comic Paul Thomas Anderson creation centered on military obsession. Anderson himself had a night to remember, collecting his first-ever Oscars for Best Adapted Screenplay and Best Director. Having long been considered one of the most brilliant unrecognized filmmakers in America, Anderson’s wins drew enormous warmth from the industry.

Conan O’Brien’s hosting was sharp and thoughtful. He opened with a monologue that referenced artificial intelligence in the entertainment industry and celebrated the extraordinary international diversity of the nominees. His framing of the ceremony as a space for hope and human connection felt genuine rather than performative.

Michael B. Jordan claimed Best Actor for Sinners over Leonardo DiCaprio, completing a memorable night for a performer who has been building toward this moment for years. The 2026 Oscars delivered a ceremony worthy of the history it produced.