Oscar Seasoning: The Supporting Battle of Benicio Versus Sean

One Battle After Another’s dominance of the 2026 Oscar season has been set in stone since its premiere. It’s Paul Thomas Anderson’s time, so we’ve all agreed. We didn’t give it to him for The Master or Inherent Vice or Phantom Thread or Licorice Pizza, but now he has a bona fide commercial hit on his hand as well as some of the best reviews of his career. This is just his moment, and rightly so. Inherent Vice is still my favourite of his, but I don’t expect Hollywood to have taste as excellent as mine.

The main five of the cast have done exceptionally well with critics’ awards, and recently earned a record-breaking seven nominations with the Actor Awards (formerly the SAG Awards, and yes, the name change is silly.) Leo’s battling Timmy, Teyana Taylor is having her “A Star Is Born” moment, and so is Chase Infiniti. And in Supporting Actor, it’s co-star versus co-star: Benicio del Toro versus Sean Penn.

Before the critics awards were announced, there was this sense among many that Penn would be the easy choice in this category because his role is bigger and more varied, but there was a lot of love for del Toro’s sly and funny performance which has the most quotable lines (“A few small beers.”) Both are great in the movie, and yet it now seems like the winds have shifted in favour of Benicio over Sean. Del Toro won Best Supporting Actor at the New York Film Critics Circle, which is a huge deal and is viewed as a key Oscar precursor. What happened?

(Image via Warner Bros.)

In One Battle After Another, Penn plays Steven J. Lockjaw, a stiff-necked soldier who develops an obsession with Perfidia Beverly Hills, a left-wing revolutionary who sexually humiliates him during a raid on a detention centre. He’s a parody of masculinity and white male ego fantasies, a wannabe tough guy who is both extremely stupid and wildly dangerous. His dreams of joining a white supremacist secret society are put at risk by his involvement with Perfidia. Penn’s doing some of his finest work here. I straight-up do not like Penn in 90% of roles (Milk is one exception), and I think he’s great here. Gross dude in real life, of course, but it ends up being helpful in his portrayal of a loser goofball who’s also a fascistic nightmare. He’s all flexed muscles and gritted teeth, like a bad drawing of a bad guy, but it’s so believably human. Watching him suffer is too dang fun.

Usually, this is the kind of performance that would be a tough sell to the Academy, but there’s so much love for OBAA and the ways it lets these two major movie stars – Leo and Penn – off the leash as weird losers on different ends of the lovable spectrum. Imagine if Kevin Kline in A Fish Called Wanda was crossed with Patton and Kevin Bacon in Animal House.

By contrast, there’s Benicio del Toro as Sergio St. Carlos, a karate teacher and leader of the undocumented community in Baktan Cross. He’s a perennially chill revolutionary with good advice and a drink always on hand. Truly, he’s an icon. He’s who you want to be in charge when war begins, and he offers a safe port in the storm when DiCaprio’s schlubby dad is too stoned to function. There are wonderful moments of subtle physicality as well as some classic slapstick, like his DUI test. He’s not as rich a character as Lockjaw, but no less fully realized.

(Image via Warner Bros.)

So, why are voters seemingly leaning towards del Toro more than Penn? Is it the role or the actor or something else? Both would be repeat winners if they took home Best Supporting Actor. Penn has two statuettes to his name, and del Toro has one, so it’s not that. Neither was more lavishly reviewed than the other. There’s not been any backlash to either character, even amid some of the denser discourse surrounding OBAA. Honestly? I think people just enjoy Sergio St. Carlos so much that they want to celebrate that. He’s a fun and cool dude, and sometimes that’s enough. It might also just be easier to reward the beer-loving hero character and not the white supremacist with a fetish for Black women.

I do wonder if there is residual hesitation around elevating Penn, a known arsehole with anger issues who seems like a genuine nightmare to be around. The rumours around what he may or may not have done to Madonna persist to this day, even though both have denied them. There’s a reason he’s the actor that Team America used as their figurehead for smug liberals who people are annoyed by, even if they agree with their politics. Then again, that never stopped the Academy from rewarding him twice (and nominating him for I Am Sam, oh dear lord, remember that?!)

This race is, of course, still pretty open. That Critics’ Choice Award win for Jacob Elordi was a reminder that the Supporting Actor race is more crowded than it was previously given credit for. We’ve got Penn, del Toro, Elordi, Stellan Skarsgard, Miles Caton, Adam Sandler, Delroy Lindo, Paul Mescal, Jeremy Strong, and Andrew Scott in the battle. I think del Toro, Penn, Elordi, and Skarsgard are the surest for the nom, but that fifth spot? There’s a fight. I would love to see Delroy Lindo FINALLY get some recognition, if only because I’m still furious he wasn’t nominated for Da 5 Bloods, where he gave one of the greatest performances I’ve ever seen. Sadly, he’s been weirdly absent in precursor noms. I do not get it, guys.

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Both Penn and del Toro are out there campaigning for it, and if One Battle After Another sweeps as many are predicting it will, it feels like the tides would be in their favour. Precursors will be key here, but they’re also up against the very tall Jacob Elordi and the endlessly charming industry regular Stellan Skarsgard (who has never been nominated before.) Usually, the Oscars balk at nominating younger actors, but both Elordi and Chalamet are leading the fight to change that. Elordi is hot right now and has Wuthering Heights on the way next month. But Stellan has seven tall sons he could send out to fight for him.

If I had to pick between del Toro and Penn, I’d probably go for del Toro too because that character is so memorable, and I’m a sucker for an actor who does so much with so little screentime. But this is also because I’m not sure I could hold my nose to vote for Penn. Yeah yeah, “separate the art from the artist” and all that, but come on, who among us, or the Academy, actually does that? It’s all a popularity contest, and the one people like the most wins. And people like Benicio del Toro. Have you heard the rumours about him being very good at, uh, romance? Just saying.