2026 Oscars Best Supporting Actor Prediction: Which Performance Has The Best Chance To Win

As the Oscars approach, we here at Looper are taking a closer look at the five biggest races of the evening — namely, the four acting races as well as best picture. So who's the most likely nominee to win supporting actor? That would be Sean Penn, who plays Colonel Steven J. Lockjaw in Paul Thomas Anderson's likely best picture winner "One Battle After Another."

Penn, who already has two Academy Awards — both in the best actor category with one for 2003's "Mystic River" and the second for "Milk" in 2008 — does seem like a "lock," pun intended, to win supporting actor at the 98th Academy Awards on March 15. Why? One must only look at the precursor awards. In the lead-up to the 2026 Academy Awards, Penn won for male actor in a supporting role at the Actor Awards (previously known as the SAG Awards and run by the actors' guild, one of the Academy's biggest voting bodies), and he also took home a BAFTA.

While Penn is the likeliest option as of this writing, the supporting actor race is still very much up in the air. Penn's fellow Oscar nominee Stellan Skarsgård took the Golden Globe for best supporting actor thanks to his role as playwright and absent father Gustav Borg in Joachim Trier's "Sentimental Value," and the other nominees who could cause an upset on Oscar night are Delroy Lindo for "Sinners," Jacob Elordi for "Frankenstein," and Benicio del Toro, also for "One Battle After Another." While it does admittedly feel frustrating that Penn is on the precipice of winning Oscar number three before either Lindo or Skarsgård win an Oscar at all — del Toro has one for his supporting turn in Steven Soderbergh's great movie "Traffic" — there's also a sense of inevitability here.

Even if you think it's boring for Sean Penn to cruise toward a third Oscar in such a crowded and competitive category, he's great in "One Battle After Another." As a refresher, Penn's Colonel Steven J. Lockjaw is the main antagonist in the story, which centers otherwise around a vigilante group known as the French 75. When the story begins, we follow the romance between Perfidia Beverly Hills (Teyana Taylor) and explosives expert Pat Calhoun (Leonardo DiCaprio), but when they have a baby girl together, everything falls apart. Perfidia, as it happens, also knows Lockjaw — who caught her planting a bomb in an office building and leveraged this knowledge into a sexual relationship with long-lasting ramifications.

Penn is equally terrifying and buffoonish as Lockjaw, right down to the bizarre way he purses his lips and twitches his mouth to the way he walks, as if he has a steel rod shoved into an unmentionable place. As he feverishly pursues Willa Ferguson (Chase Infiniti) — that baby girl who now lives in hiding with Pat, now renamed Bob Ferguson — believing that she's biologically his and could prevent him from joining a secret white supremacist society known as the Christmas Adventurers, Lockjaw is dogged, silly, and incredibly sinister. It is, truly, an award-worthy performance.

Still, the supporting actor category is full of great nominees. Jacob Elordi, who plays the monster in Guillermo del Toro's "Frankenstein," is magnificent under all of that makeup, and Stellan Skarsgård deserved that award for "Sentimental Value." Delroy Lindo, one of many standouts in Ryan Coogler's "Sinners," would be a great winner, but there's one real dark horse in this race, and it's Penn's co-star.

Sean Penn and Benicio del Toro don't share any screen time in "One Battle After Another," but they both provide truly astonishing supporting performances. Del Toro plays Sensei Sergio St. Carlos, who we first meet as Willa's karate instructor and who turns out to be vital in Bob's quest to rescue Willa from Lockjaw's gnarled clutches. Sensei Sergio springs into action when Bob tells him that Willa might be in danger, and as we watch him give Bob shelter and a weapon, we also learn that he's basically operating an underground railroad of sorts, helping undocumented immigrants escape the federal government through a series of passageways that lead them to safety. When Bob ends up hospitalized after falling from a rooftop during a heated chase, Sensei Sergio is there with the getaway car — and a few Modelos, or, in his parlance, a few "small beers."

Del Toro is at his most charming with extremely limited screen time in "One Battle After Another," and he delivers such a fun and unexpectedly resonant performance that it would genuinely be exciting to see him cause an upset in the supporting actor category. (For all of his beers and roadside dancing, Sensei Sergio's commitment to helping his community by hiding them from sinister forces and preventing their imprisonment is genuinely touching.) Still, this seems like Penn's award to lose, even if he might barter it for a cigarette at an afterparty. (No, really — he keeps smoking inside.) We'll have to see how this race and all of the others shake out on March 15 at the Academy Awards; they air on ABC and Hulu at 7 p.m. EST.