Oscars 2026: A Night Where Everything Happened Except Sean Penn Showing Up

Everything the 98th Academy Awards needed for a legendary evening was present — records, surprises, stellar hosting, and genuine emotion. Everything, that is, except Sean Penn. Penn won Best Supporting Actor for One Battle After Another, claimed his third career Oscar, tied the all-time male acting record, and was not in the building. Presenter Kieran Culkin filled the void with aplomb, delivering a joke about Penn’s absence and collecting the trophy before the show moved on.

Penn’s three Oscar wins now tie him with Jack Nicholson, Walter Brennan, and Daniel Day-Lewis for the most acting wins in Academy history by a male performer. His previous wins — for Best Actor in Mystic River and Milk — were recognized as benchmarks of their respective years. This third win, for a supporting role, completes an Oscar legacy that has no real parallel in contemporary cinema.

One Battle After Another gave Penn the role of a military officer defined and destroyed by his own convictions. His performance was widely praised as one of the year’s best acting achievements. Director Paul Thomas Anderson won his first-ever Oscars for the film — Best Adapted Screenplay and Best Director — completing a landmark night for a filmmaker whose work has shaped American cinema for three decades without previously receiving the Academy’s formal recognition.

Conan O’Brien was a well-received host, balancing sharp humor with sincere reflection on the power and reach of cinema. His opening monologue touched on artificial intelligence and the global scope of the nominees — 31 countries and six continents. His performance was praised as one of the more assured hosting efforts in recent Oscar memory.

Michael B. Jordan’s Best Actor victory for Sinners over Leonardo DiCaprio was among the most celebrated results of the night. The 2026 Oscars had everything they needed for a legendary evening — and they got it, with or without Sean Penn in the room.