Conan O’Brien’s First Oscars as Host Was Also Sean Penn’s Third as Winner

There is a pleasing symmetry to the 98th Academy Awards: Conan O’Brien hosted the Oscars for the first time, and Sean Penn won the Oscars for the third time. One man was very much present for the occasion; the other was not. Penn’s Best Supporting Actor win for One Battle After Another — his third career Oscar, tying the all-time male acting record — was accepted by a wry Kieran Culkin in the absent winner’s place. O’Brien, for his part, was firmly onstage and doing an excellent job.

Penn’s three wins now tie him with Jack Nicholson, Walter Brennan, and Daniel Day-Lewis in the record books. His previous wins were for Best Actor — Mystic River in 2004 and Milk in 2009 — and his latest, for a supporting role, adds an entirely new category to his Oscar legacy. Few actors in history have won across both lead and supporting categories.

Penn’s character in One Battle After Another is a military officer whose obsessive commitment to his beliefs becomes his greatest vulnerability. Critics described the performance as one of the most compelling of Penn’s career, which is saying a great deal given the standard he has set across 30 years of film work. Director Paul Thomas Anderson won his first Oscars for the same film — Best Adapted Screenplay and Best Director — completing a historic night for the production.

O’Brien’s hosting was sharp, warm, and well-paced. He opened with a monologue that addressed artificial intelligence as a genuine threat to people working in entertainment, and he spent real time celebrating the 31 nations represented among the nominees. His framing of the ceremony as a global gathering was one of the more thoughtful approaches to an Oscars opening in recent years.

Michael B. Jordan won Best Actor for Sinners over Leonardo DiCaprio. The 2026 Oscars, with their records, firsts, and notable absences, were exactly the kind of evening that makes the ceremony worth watching every year.