Sean Penn has fended off stiff competition to win best supporting actor at the Actor Awards 2026, putting the One Battle After Another villain in pole position to win the Oscar in two weeks — a stunning turn of events after Penn had lost the Golden Globe, the Critics Choice Award and most other precursors.
Penn’s momentum began last weekend at the BAFTA Awards, where he came out of nowhere to pull off a massive upset in the equivalent category, overtaking frontrunner Stellan Skarsgard (Sentimental Value). While he was not widely considered win-competitive a few weeks ago, Penn will now go into the Oscars having taken home both trophies from industry groups with significant Academy overlap. This is to say, it’s safe to consider him the frontrunner at this point.
And yet: Penn was not in attendance for either tonight’s ceremony nor last weekend’s BAFTA Awards. He’s eschewed the spotlight relative to his One Battle colleagues but has been present for other shows over the season like the Golden Globes (where he was also nominated). His nominated co-star Leonardo DiCaprio was also not present due to his filming on Martin Scorsese’s new film.
This Actor Awards 2026 race was considered something of a free-for-all, with neither Skarsgard (who won the Golden Globe) nor Sinners’ Delroy Lindo, who’s seeing late-breaking momentum of his own, even nominated by SAG-AFTRA. Instead, Penn beat out fellow Oscar nominees Jacob Elordi (Frankenstein), who pulled off an upset himself at the Critics Choice Awards, and Benicio Del Toro, his One Battle costar who dominated the early critics’ awards circuit but hasn’t won any of the televised awards. SAG-AFTRA also nominated Hamnet’s Paul Mescal and Sinners’ Miles Caton, who were overlooked by the Academy.
This is Penn’s second Actor Award, following his lead-actor victory for Milk, which led to his second Oscar. He won his first Oscar for Mystic River, for which he lost the Actor Award to Pirates of the Caribbean’s Johnny Depp; he’s also been nominated by SAG-AFTRA for Dead Man Walking and I Am Sam. He could take home a third Actor Award later tonight for his part in the One Battle After Another ensemble.
