How to Pick an Oscar-Winner and Win Money

We asked a betting expert to do the work for us, and it looks like 'La La Land' has this in the bag. 


Hollywood stars don’t have to be the only people getting their hands on some sweet gold during the Academy Awards. Betting on major sporting events like the Super Bowl and NCAA Tournament are American traditions, but over the last few years, Oscar betting has become an alternative for the more showbiz-minded. Want in? Then we’re here to help: Inverse asked expert odds-maker Raphael Esparza about betting on the 89th Academy Awards ceremony.

Esparza is a former sportsbook director for companies in Las Vegas, but also covers entertainment odds for online betting site Doc’s Sports. Having spent time with big-time gamblers, Esparza sees Oscar betting as a safe place for casual fans to filter their fandom and make a little coin. “You’re not going to pay for your mortgage when putting money down on the Oscars,” he told Inverse. “The Oscars are a fun betting event where you can sit there and watch the entire four-hour show filled with small betting possibilities.”

Compiling the odds for events where winners are determined by voting is different than, say, an event where one team simply beats another. There are many factors that go into calculating who has the best odds of winning a little gold statue, but it starts with keeping everything in context.

“I’m not only looking for who will probably win the award, but also the categories as a whole,” Esparza told Inverse. “For the Oscars, you make odds for what kind of money you think is going to come in, but also and how you can protect the house.”

Esparza used critical darling La La Land as an example. “I hate to use the word ‘lock’ on anything, but La La Land has a lot of hype. At the same time, you can’t really raise the odds more for Moonlight or Manchester by the Sea,” he said. “Hidden Figures is getting a lot of attention right now, but if you judge movies like that too high, you’re going to expose yourself. We protect the house but prepare ourselves for what’s most likely to win.”

So what is most likely to win the major categories? Here’s what Esparza had to say about each category.

Best Picture

“I base a lot of my predictions on the Director’s Guild Awards,” he said. And frontrunner La La Land took home the DGA’s top award, which might solidify its Oscar chances. And peripheral factors help it rise above its rivals. “Arrival is so far down because of pressure from other films, and there’s a backlash against Hacksaw Ridge because of Mel Gibson,” he said. “With La La Land also sweeping the Golden Globes and the SAG awards, you have to interpret the numbers from those previous awards ceremonies.”

Predicted Winner: La La Land

Best Director

Normally the Best Director and Best Picture awards go hand in hand, but Alejandro González Iñárritu’s win last year for directing The Revenant and Spotlight’s surprise Best Picture victory threw that assumption out the window.

“If there is an upset it might be Barry Jenkins,” Esparza said, referring to the Moonlight director. “You look at the #OscarsSoWhite controversy last year and that might sway voters beyond Moonlight being incredible. He could squeak in as a big surprise, but I just don’t think Damien Chazelle is going to lose.”

Chazelle currently stands at a -3000 bet, a huge margin in any category. “If Chazelle lost it would be one of the biggest upsets in a long time,” Esparza said.

Predicted Winner: Damien Chazelle

Best Actor

The close Best Actor race looks to be down to two actors: Denzel Washington for Fences and Casey Affleck for Manchester by the Sea.“It’s very rare to have a big category be so close like that since the last few years have been a landslide,” Esparza said, citing Eddie Redmayne’s win for The Theory of Everything and Leonardo DiCaprio in The Revenant.

But Esparza said the hype from other categories might give the Oscar gold to Affleck. “Everyone knows that Viola Davis is going to win the Best Supporting Actress award for Fences, and it’s very rare to see Supporting Actress and Actor come up for the same movie,” he said. “I figure Viola Davis is the biggest favorite of the whole ceremony, so that leaves room for Casey Affleck, who also already won the Golden Globe for Best Actor.”

Predicted Winner: Casey Affleck

Best Actress

Anytime Meryl Streep is up for a Best Actress award, you should usually take notice … except for this year. “With La La Land being so hyped, and Ryan Gosling not high up on the Best Actor list, Emma Stone has probably got it,” Esparza said. For the past five years in the current voting scheme, any nominee at -1000 or higher has won the Best Actress award, and Stone is creeping toward that number.

But Esparza says not to count out a former front-runner. “That’s a phenomenal performance,” he said of Natalie Portman’s turn as former First Lady Jacqueline Kennedy in Jackie. “There could be an upset. It’s Emma Stone’s to lose, but I would not be shocked if Natalie Portman took it home.”

Predicted Winner: Emma Stone

Those are just the main categories, but there are 24 other announced categories to choose from. Esparza said it might even be better to focus your bets on the smaller categories, and to not count out movies next to what seem like clear shoe-ins.

“Disregard stuff that you think can’t lose,” he said. “That’s why Oscar betting is so popular. Last year’s odds were seriously against Ex Machina winning Best Visual Effects, but it won. How often in betting do you see a 70-1 shot win?”

See if you win big when the 89th Academy Awards air on February 26, 2017.

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