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2026 Oscars Best Supporting Actor Prediction: Sean Penn vs. Stellan Skarsgard?

Best Supporting Actor nominee Sean Penn at the premiere for "One Battle After Another."
Photo by Scott A Garfitt/Invision/AP

As usual, there’s a loaded group of nominees who can win the Academy Award for Best Supporting Actor at Sunday's 2026 Oscars, beginning at 7:00 p.m. ET on ABC.

Sean Penn is currently the clear favorite to take home the award for his role in "One Battle After Another," according to user picks on prediction markets like PrizePicks.

For those who want to make Oscars predictions on winners for every award, PrizePicks Culture Picks is the place to do it, available in 48 states. On Culture Picks, you can make predictions and real-money payouts, if you're right, including on best picture, best actor, best actress, and more.

Let’s take a look at the Oscar for Best Supporting Actor nominees, favorites, and our Best Supporting Actor prediction.

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2026 Oscars Best Supporting Actor Nominees: One Battle After Another Leads the Way

As one of 13 Oscar nominations for "One Battle After Another," Sean Penn is the current favorite to win Best Supporting Actor, according to user picks on PrizePicks Culture Picks. Stellan Skarsgard is currently slated as the expected runner-up to Sean Penn for his role in "Sentimental Value." 

The numbers below represent the real-money payout multipliers for predictions on the Oscars Best Supporting Actor winner; a $100 entry on Sean Penn to win the award pays out $126 if you’re right on PrizePicks.

Sean Penn: Yes 1.26x | No 3.84x

Stellan Skarsgard: Yes 5.88x | No 1.13x

Delroy Lindo: Yes 10x | No 1.05x

Benicio del Toro: Yes 33.33x

Jacob Elordi: Yes 33.33x

Tie: Yes 33.33x

Note: Payout multipliers are based on the implied probability of each outcome; these payouts reflect market value and user predictions. Lower multipliers indicate the public believes that outcome is more likely.

Culture Picks data is live at the time of writing and is subject to change.


2026 Oscars Best Supporting Actor Winner Favorites

Here are the favorites to win Best Supporting Actor at the 2026 Oscars. Check out more of our 2026 Oscars predictions and Culture Picks on Playbook.

Sean Penn

To Win: Yes 1.26x | No 3.84x

As a convincing villain named Steven J. Lockjaw in "One Battle After Another," Sean Penn has received plenty of recognition at non-Oscar award ceremonies. Ahead of this year’s Oscars, Penn has already taken home the BAFTA (the first of his career) and the Best Actor Award (SAG) for Supporting Actor.

Stellan Skarsgard

To Win: Yes 5.88x | No 1.13x

While Penn is expected to win the 98th Academy Award for Best Supporting Actor, Stellan Skarsgard has earned critical acclaim as a film director and troubled father named Gustav Borg in "Sentimental Value." At this year’s Golden Globes, Skarsgard received the award for Best Supporting Actor in a Motion Picture.

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2026 Oscars Best Supporting Actor Prediction

Here is our prediction to win Best Supporting Actor at the 2026 Oscars. To get in on the action and earn real money on the 2026 Oscars, head over to PrizePicks Culture Picks — available in 48 states.

There’s a real argument to be made for any of Sean Penn, Stellan Skarsgard, Delroy Lindo, or Benicio del Toro to win Best Supporting Actor. That being said, Penn received rave reviews for his acting efforts in "One Battle After Another" when the movie hit theaters — and his success at other award shows reflects that.

Furthermore, "One Battle After Another" is the favorite to win Best Picture at the 2026 Oscars with a 1.25x payout, per PrizePicks Culture Picks.

Penn already has two Oscars to his name, earning the Best Actor honor in 2004 for "Mystic River" and again in 2009 for "Milk." On the other hand, Skarsgard received his first career Oscar nomination for "Sentimental Value."

Besides being the first actor to receive a Best Supporting Actor nomination for an international film, there may be a slim chance the Academy elects to reward Skarsgard instead of Penn to give him his first Oscar. However, it’d be quite the surprise to hear anyone but Sean Penn hear his name called when the envelope is opened.


Make Real-Money 2026 Oscars Predictions on PrizePicks

Sean Penn is in a prime position to add to his collection of Oscars, but Stellan Skarsgard and other nominees make this year’s Best Supporting Actor category a loaded group.

You can make your 2026 Oscars predictions on PrizePicks Culture Picks and earn real money. With Culture Picks, make predictions on various subject matters, and cash in if you’re correct, now available in 48 states.

Keep tabs on the Playbook for continued 2026 Oscars predictions and other pop ulture picks.

Get in the game! Sign up for PrizePicks and cash in on your sports predictions. Play $5 and get $50 instantly in Lineups with promo code PLAYBOOK.

Team Picks and Culture Picks are event contracts offered by Performance Predictions II, LLC d/b/a PrizePicks Predict, a CFTC-registered FCM and NFA Member. All event contract customers must be U.S. residents and 18+. Some event contracts may not be available in every state. Event contract trading carries significant risk and is not appropriate for everyone. No guarantee against loss is offered. Past results are not necessarily indicative of future results. Void where prohibited by law. Restrictions apply. For full terms of service see prizepicks.com/predict-regulatory. Team and Culture Pick Early Payouts subject to market liquidity. The content provided is for informational and educational purposes only and does not constitute investment advice, or a recommendation to trade any commodity interest.

about the author

Skyler Carlin is an experienced writer with nearly 10 years of experience writing and editing NFL, NBA, MLB, CFB, CBB, & soccer content for FanDuel Research & USA Today. When he’s not writing, he enjoys cooking, watching movies, & playing video games.

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