Tuesday, February 24, 2026

Is The Best Supporting Actor Race Back To Being Sean Penn’s To Lose?

It seemed that when “One Battle After Another” premiered in September, Sean Penn’s despicable, instantly iconic Steven Lockjaw would earn him his third Oscar. As this award season began to unfold, we were told a different story, with his costar Benicio Del Toro surprisingly winning many of the early critics groups, including the New York Film Critics Circle and the National Board of Review. After losing the Golden Globe and Critics’ Choice, it seemed Penn’s chances were taking hit after hit, but after winning the first industry award of the season, one has to wonder how much of a race is left in the category.

With “One Battle After Another” being such a dominant film all season, it’s been strange not to see its prominent, very showy villain come alongside its all-too-common sweep. It seemed like his past wins, and perhaps the bad will toward his personality and public persona, were preventing him from going very far this season, but perhaps those narratives weren’t as powerful as we thought. Many expected Stellan Skarsgård to repeat his Golden Globe win at BAFTA for “Sentimental Value,” but with the loss this weekend and the lack of a nomination at the Actor Awards, it sadly seems he may have to sit out of the win conversation going into the Oscars.

With Jacob Elordi winning Critic’s Choice for “Frankenstein,” there’s a chance he could repeat at the Actor Awards, but, likely, this combo wouldn’t even be strong enough to take down another precursor-winning performance in the Best Picture winner. This win for Penn feels very reminiscent of Mikey Madison’s BAFTA win for “Anora” and how it was the ultimate foil to Demi Moore’s near-televised precursor sweep for “The Substance.” When you’re the Best Picture winner with an industry award under your belt, it seems almost impossible for you to lose the Oscar, and with a performance as baity and talked about as Penn’s, his ending the season as a winner with the film makes sense on paper.

With the notion of industry awards for actors in Best Picture winners, that brings the Actor Awards into the equation, and the potential for Benicio Del Toro to take the win there. In a world where Del Toro does take the Actor this weekend, it would be a very heated debate leading up to the Oscars over who actually has momentum between Del Toro, Penn, Elordi, Skargård, and yes, even Delroy Lindo. There’s obviously a world where Penn repeats this weekend, but with a character that depraved and an actor that divisive, it isn’t hard to see SAG-AFTRA having the same problem early critics did with rewarding him. If this “One Battle After Another” split were to happen, it would clearly be a very, very close Oscar race. Still, Oscar tends to lean towards the more “international pick” of the nominated performances, and Penn has now established himself as one who would track more with their recent history.

It would be the most exciting race we’ve seen in an acting category in some time, and just for fun stats purposes, Del Toro at SAG would make this the first time a supporting acting category has split four ways at the main precursors since Best Supporting Actress in 2007 and the first time overall since Best Actress in 2020. In a world where Elordi wins this weekend, many will make arguments for him to win the Oscar, and there are arguments to be made. However, it would still be a weaker argument than Penn’s performance in a film that has loomed this large this awards season. An Elordi win could prompt people to argue the race is split enough for an upset in someone else’s favor. Still, it really seems any hope of seeing Skarsgård win the Oscar died the other day with Penn’s BAFTA win. Perhaps, in hindsight, Skarsgård’s Actor award miss wasn’t taken seriously enough as a massive hit to his campaign.

Sean Penn in “One Battle After Another” is a type of villain role we saw the Academy reward often in the past, and, frankly, a type of win we haven’t seen as much recently. Winners in this category have leaned much more towards the hearts of their respective films in recent years, like Troy Kotsur in “CODA” or Ke Huy Quan in “Everything Everywhere All At Once.” While this trend made Penn’s weakness in this race earlier in the season easier to accept, his bursting back into the race in a big way and ultimately taking the Oscar will put this race right back where it seemed to be months ago, when the film first opened. With “One Battle After Another” looking to have such a big night on March 15th, perhaps it always made sense for the film’s most potent and talked-about character to be on stage alongside it on Oscar night…that is, if Penn decides to show up.

Do you think Sean Penn is winning a third Oscar? Do you see a path for anyone else to win the Oscar at this point? Who are you predicting Please let us know in the comments section below and on our X account, click here here for the most recent tally of awards season winners, here for Next Best Picture’s precursor tracker, and here for our current Oscar predictions.

Subscribe to Our Newsletter!

Related Articles

Stay Connected

114,929FollowersFollow
101,150FollowersFollow
9,315FansLike
9,410FansLike
4,686FollowersFollow
6,055FollowersFollow
101,150FollowersFollow
9,315FansLike
4,880SubscribersSubscribe
4,686FollowersFollow
111,897FollowersFollow
9,315FansLike
5,801FollowersFollow
4,330SubscribersSubscribe

Latest Reviews