The Four Men Who Own Oscar History — and Their Shared Record of Three Wins

In nearly a century of Academy Awards, only four men have won three acting Oscars. Walter Brennan did it first. Jack Nicholson second. Daniel Day-Lewis third. And Sean Penn is the fourth. Penn’s Best Supporting Actor win at the 98th Academy Awards for One Battle After Another completed a record that has stood, in various forms, for decades. That he achieved it without attending the Dolby Theatre is precisely the kind of detail that seems to define Penn’s approach to almost everything.
Presenter Kieran Culkin accepted the award in Penn’s absence and offered a memorable line about the actor’s failure to attend. The audience laughed and applauded, and the ceremony moved on — though Penn’s record remained the headline. His previous Oscar wins — for Mystic River and Milk — were celebrated at the time as defining performances of their respective years.
Penn’s character in One Battle After Another is a dogmatic military officer who loses himself in his own ideology — a role the actor inhabited with complete conviction. Director Paul Thomas Anderson won Best Adapted Screenplay and Best Director for the same film, his first two Oscars after a career spent producing some of the most admired American films of the last three decades. The industry’s response to Anderson’s wins was one of pure, genuine delight.
Conan O’Brien opened the evening with a monologue that touched on artificial intelligence and the future of entertainment before settling into a warm celebration of the nominees’ international diversity. With participants from 31 countries and six continents, the 98th Oscars were a genuinely global event in a way the ceremony has not always managed to be. O’Brien acknowledged that with evident pride and sincerity.
Michael B. Jordan took Best Actor for Sinners over Leonardo DiCaprio, rounding out a night full of landmark results. The four men who share the all-time male acting record now include one who won his third while watching from somewhere else.