Hollywood’s Most Decorated Male Actors Have Company: Sean Penn Joins the Club

The exclusive club of male actors with three Oscar wins gained a new member on Sunday night — Sean Penn — even though the newest inductee was nowhere near the Dolby Theatre when his name was announced. Penn won Best Supporting Actor for his searing performance in One Battle After Another, tying the all-time record for male acting wins at the Academy Awards. Presenter Kieran Culkin stepped in to accept the award and delivered a memorable quip about Penn’s notable absence.

Penn now shares the record with Jack Nicholson, Walter Brennan, and Daniel Day-Lewis, all of whom won three Oscars over their respective careers. What makes Penn’s achievement particularly striking is that he has won in both major acting categories — twice as Best Actor and now once for Best Supporting Actor. His journey to three Oscars spans more than 20 years of extraordinary film work.

The film behind his latest win, One Battle After Another, is Paul Thomas Anderson’s darkly comic and psychologically rich thriller. Penn portrays a military officer trapped by his own obsessive worldview, a performance critics have compared favorably to some of the most celebrated screen acting of the past decade. Anderson had a superb evening personally as well, collecting Oscars for Adapted Screenplay and Best Director.

Host Conan O’Brien struck an optimistic tone while acknowledging the turbulent state of the world. His observation that nominees represented 31 countries on six continents underscored the global significance of the ceremony. He also made headlines early on with a joke about being the “last human host” before AI takes over the entertainment industry.

Michael B. Jordan’s Best Actor win for Sinners was among the evening’s other major results, with Jordan beating out Leonardo DiCaprio for the prize. All told, the 98th Academy Awards delivered a night full of genuine drama — including an acceptance speech that never came.