Richard Roeper’s 2026 Oscars predictions are here

The 98th annual Academy Awards are a week away, so let’s look at some of the pressing questions about this year’s ceremony — and my picks in the four acting categories plus best picture.

I expect to see “One Battle After Another” and “Sinners” split the evening, with five total wins apiece; “Frankenstein” taking home as many as four Oscars in four craft categories; “KPop Demon Hunters” winning for best animated feature and original song; and nine other films/performances winning one Academy Award.

That so many of the major categories are still up for grabs this late should make for one of the most entertaining and unpredictable Oscars in recent years.

What’s new or noteworthy about this year’s Oscars?

These Academy Awards have already made history. With 16 nods, “Sinners” has set the record for the most nominations, besting “All About Eve” (1950), “Titanic” (1997) and “La La Land” (2016) with 14 apiece. They’ve also added best achievement in casting — the first new category since best animated feature was introduced in 2001.

When does voting close for the Academy membership, and how will that impact the final tally?

Voting for the 2026 Oscars began on Feb. 26 and closed Thursday at 5 p.m. Pacific Time. This is significant because many of the approximately 10,000 voters wait until the last day or two to cast their ballots. Momentum gained — or lost — from the Producers Guild Awards and Actor Awards can be a significant factor, especially in the case of the latter, as actors make up the largest voting bloc.

Do any of this year’s nominees have Chicago ties?

Supporting actress nominee Amy Madigan grew up in South Shore and graduated from (the now defunct) Aquinas High School. Her father was John Madigan, the legendary journalist and fixture at WBBM-Newsradio and CBS-2 Chicago. Also, Madigan played one of the all-time great girlfriends in one of the most beloved Chicago-area comedies ever, “Uncle Buck,” in which she was comedic gold opposite John Candy as the kind and patient but exasperated Chanice Kobolowski.

Can I bet on the Oscars?

Yes and no. A number of platforms, including DraftKings and FanDuel, offer wagering on the Oscars in some states — but Illinois blocks awards betting on those sites. Illinois residents are allowed to wager on the Oscars via Kalshi, which offers contracts on the major and niche categories, as well as the specific number of wins for a specific film. For example, there’s a 16% chance “One Battle After Another” will win exactly five Oscars. If you place a $10 bet and it hits, you’d make a net profit of about $53. You can also speculate on “Who will attend the Oscars?” There’s a 99% chance Kylie Jenner will attend, which means that if you make a 99-cent investment, your return will be $1, congratulations! Ryan Gosling is at 61%, while Taylor Swift is a long shot to attend at 4% — so if you wagered $10 on Swift attending and she shows up, you’d realize a net profit of about $240. Friendly advice (from the guy who wrote a book titled “Bet the House: How I Gambled Over a Grand a Day on Sports, Poker and Games of Chance”): If you’re going to place a wager on the Academy Awards, limit it to the amount you’d spend on a popcorn and a drink at the movies. Enough to celebrate if you win, but not to feel pain if you don’t.

What’s this I hear about the Oscars moving to YouTube?

Starting in 2029 through 2033, YouTube will be the exclusive global platform for the Oscars, streaming the event live and free worldwide.

ABC has been the television home of the Academy Awards since the “One Flew Over the Cuckoo’s Nest” triumph at the 1976 ceremony. Last year, Hulu joined as a streaming partner. The ABC/Hulu pairing will continue through the spring of 2029, when YouTube will host the Academy Awards, becoming home base for arguably the biggest night in show business. In a world where Peacock and Prime Video carry NFL games and where Netflix, FX and HBO and AppleTV+ are forces at the prime-time Emmys, this move now seems almost inevitable.

Traditionally, the Academy of Motion Picture Arts and Sciences has been about as agile as the woolly mammoth when it comes to adapting to the times — but over the past decade, in the wake of reportage that found the voting membership was whiter, older and more male than the moviegoing public, not to mention the #MeToo and #OscarsSoWhite movements, the Academy launched a massive effort to diversify and expand membership, and to ensure a more inclusive nomination process.

Here are my predictions for who will win — and who should win — in five major categories (scroll to the bottom of this story for a complete, downloadable 2026 Oscars ballot, with Roeper's picks in bold):

Actress in a supporting role

Will win: Amy Madigan (“Weapons”)
Should win: Amy Madigan
Contenders: Teyana Taylor (“One Battle After Another”), Wunmi Mosaku (“Sinners”)

After Teyana Taylor’s Golden Globes win, she was the favorite — but Wunmi Mosaku’s win at the BAFTAs tightened the race, which became even more competitive with Amy Madigan’s name being called at the Actor Awards. By luck of the release schedule, this is one of the toughest competitions of the past 20 years. At 75, Amy Madigan is at least a generation older than the other nominees, and yes, sentiment sometimes sways the vote. Taylor and Mosaku left indelible impressions with their respective performances, but Madigan has the kind of flashy, over-the-top, utterly mad role that attracts attention. I mean, Gladys looks like Weird Barbie’s psychotic mom, yet Madigan somehow managed to make her more than a carnival sideshow.

Actor in a supporting role

Will win: Sean Penn (“One Battle After Another”)
Should win: Delroy Lindo (“Sinners”)
In the running: Stellan Skarsgård (“Sentimental Value”)

Yes, I’m hedging my bets — but this is another category where the race has taken some unexpected turns. Sean Penn’s attention-grabbing work as the grotesque Col. Steven J. Lockjaw in “One Battle After Another” has all the late juice going for it. (Penn has been one of our best actors for 40 years, but I felt his cartoonish performance took us out of the movie.) There’s a chance the universally respected Stellan Skarsgård will win for his finely calibrated work in “Sentimental Value” — but if I had a vote I’d cast it for Delroy Lindo, who is the grounded center and provides a sense of history amid all the dangerous, dreadful and violent chaos in “Sinners.” When Lindo’s world-weary Delta Slim spoke, it was as if the sound and fury around him was suddenly muted.

Actress in a leading role

Will win: Jessie Buckley (“Hamnet”)
Should win: Jessie Buckley
Other contenders: None

You know the cliché: “It’s an honor just to be nominated.” In the best actress race, it’s quite true. For the enormously talented Rose Byrne (“If I Had Legs I’d Kick You”), Kate Hudson (“Song Sung Blue”), Renate Reinsve (“Sentimental Value”) and two-time winner Emma Stone (“Bugonia”), it’s the closest thing to a mathematical certainty that the nomination will be the reward. Jessie Buckley’s magnificent, searing and raw work in “Hamnet” is among the finest performances I’ve seen in any category this decade — and it ticks off a myriad of award-prestige boxes, as it’s an actor-driven, Shakespeare-inspired, deeply tragic period piece. It’s the kind of role and performance that draws in voters, and in this case, deservedly so.

Actor in a leading role

Will win: Michael B. Jordan (“Sinners”)
Should win: Michael B. Jordan
Primary contender: Timothée Chalamet (“Marty Supreme”)

Timothée Chalamet comes across as a likable fellow who is clearly enjoying his ascension to stardom, and there’s absolutely nothing wrong with that. Chalamet is one of the most gifted actors of his generation, and until recently he appeared to be a lock to win best actor. Ah, but it’s a tricky thing when you appear to want something too much; to wit, Chalamet’s comment last year that he desired to be “one of the greats.” That might be turning off some voters. Chalamet lost at the BAFTAs in a major upset, with Robert Aramayo winning for “I Swear.” Then came the seismic moment at the Actor Awards when Michael B. Jordan won for his brilliant performance in “Sinners” — and the room erupted. At this point, it seems like a coin flip. I’m predicting Jordan will win based on the late surge of support. It was also my favorite piece of work in this group. Jordan gave us two distinct, unique, memorable characters in Smoke and Stack. The fact that one of them undergoes quite the transformation in the film almost makes this triple-character work. It’s a blazing, compelling, pure movie star performance.

Best picture

Will win: “One Battle After Another”
Should win: “Sinners”
Other contenders: None

The chances of any film other than “Battle” or “Sinners” winning best picture are about the same as a No. 16 seed upsetting a No. 1 seed in the NCAA men’s basketball tournament. Never say never — but it’s not happening. I’m sticking with my prediction of Paul Thomas Anderson’s “One Battle After Another,” which has been the favorite throughout awards season and hasn’t suffered any major setbacks. I had “Battle” as my second-best film of 2025 — just behind “Sinners.” They’re both sweeping, visually stunning, profound and yet wildly entertaining epics. But for me, “Sinners” pulled off the more difficult feat with the whiplash-inducing genre switch and some of the most exhilarating music sequences of this century.

Richard Roeper is the former Sun-Times movie critic.