'Anora' Will Clean Up At The 2025 Oscars: Best Bets For 97th Academy Awards

This is the most degenerate betting thing I've written since joining OutKick in August 2022. This says a lot considering I've given out "best bets" for the last two Nathan's Hot Dog Eating Contests. Yet, my 2025 Academy Awards article is grosser since I've only seen two of the 10 Best Picture nominees: Dune: Part Two and Conclave. Dune kicked a** and Conclave was fine (3.5 out of 5 stars). 

Nonetheless, March Madness hasn't started, football season is over, and there's only so much money I can lose on the NBA and PGA TOUR before gambling on other things instead. That said, fade or follow my 2025 Oscars action at your peril. Here are my bets for the 97th Academy Awards, hosted by Conan O'Brien and airing on ABC Sunday, March 2 at 7 p.m. ET. 

2025 Academy Awards Betting Card (DraftKings) 

• ‘Anora’ for Best Picture (-200)
• Mikey Madison for Best Actress in ‘Anora’ (+175)
• Timothee Chalamet for Best Actor in ‘A Complete Unknown’ (+150)
• Sean Baker for Best Director in ‘Anora’ (-175)
• ‘Conclave’ for Best Film Editing (-165)

Best Picture: ‘Anora’ (-200) 

Starring Madison as "Anora" aka "Ani" and Mark Aleksandrovich Eydelshteyn as "Ivan," Ani's love interest, this movie burst onto the scene, winning the coveted Palme d'Or for Best Feature Film at the Cannes Film Festival last summer. In a toss-up year like 2025, I'm gambling on the Academy deferring to the French picking an American film as the year's best.  

This is the only Best Picture nominee I haven't seen that I want to see. I'm a New York native who likes modern stories. Anora checks both boxes since it's set in Brooklyn. It's about strippers, partying, and poor/working-class people mixing it up with rich folks, and it has nudity. All awesome things. For my gambling analysis, my brother, the biggest film fan I know, who watches every Best Picture nominee, says Anora will win.

Best Actress: Mikey Madison (+175)

Demi Moore (-250) is the odds-on favorite for her performance as "Elisabeth Sparkle" in The Substance, a "body horror" flick, which is a style of movie that rarely wins Academy Awards.  Granted, Moore could win Best Actress as a lifetime achievement award based on her being a Hollywood star for decades and never winning anything.  

But, Madison had a much higher usage rate, so to speak, in Anora than Moore in The Substance. Per ScreenTimeCentral.com, Moore is 42% of The Substance while Madison appeared on-screen for 78% of Anora. If we are nitpicking (and I am), then Madison represents an "Actress in a leading role" more than Moore (damn that's annoying to say and write). 

Mikey Madison is the second betting favorite to win Best Actress at the 2025 Academy Awards for her role in 'Anora'. (Photo credit: Jay Calderon/The Desert Sun-USA TODAY NETWORK via Imagn Images)

Madison vs. Moore is similar to last year's Best Actress race between Lily Gladstone in Killers of the Flower Moon vs. Emma Stone in Poor Things. Gladstone was a -175 favorite and Stone was +125. But, Gladstone had 27% of screen time in Killers of the Flower Moon compared to Stone, who was on-screen for 69% of her movie. 

Bill Maher shared an amazing Oscars trend on this week's Real Time. Maher said 14 Best Actress winners played prostitute roles. Spoiler alert for those who haven't seen Anora yet, myself included, the Anora character played by Madison is a "lady of the night" from Brooklyn. I'm definitely giving my money to a … err, never mind. Bet Madison though. 

Best Actor: Timothee Chalamet (+150) 

Chalamet won the Best Actor award at the Screen Actors Guild (SAG) Awards for his portrayal of Bob Dylan. Ten of the 12 Best Actor winners at the SAG Awards have gone on to win the same award at the Oscars. Adrien Brody (-250) is the favorite for his role in The Brutalist while winning Best Actor at the Golden Globes and BAFTA Awards. 

Brody won Best Actor at the 75th Academy Awards for his role in The Pianist, upsetting Hollywood legends Jack Nicholson in About Schmidt and Daniel Day-Lewis in Gangs of New York. So, Brody will lose to Chalamet for the same reason Joel Embiid won the 2022-23 NBA MVP over Nikola Jokić: "Voter fatigue."

Despite being the best player in the world, Jokic lost the MVP to Embiid because he won the previous two years and basketball gatekeepers didn't think Jokic should three-peat before winning an NBA championship. Chalamet will win because the Academy doesn't want Brody to win his second Best Actor award, putting him in elite company. 

The vibes are just right with Chalamet, whose SAG acceptance speech was covered on OutKick. Chalamet said he wanted to be "one of the greats" in Hollywood, and it's rare for an actor to be so outwardly ambitious. The film industry needs more box office stars, and by awarding him Sunday, the Academy gives another way for studios to promote Chalamet's movies. 

Best Director: Sean Baker for ‘Anora’ (-175)

Pinnacle Sportsbook lists Baker's odds to win this award at -250 Friday evening. That's significant because Pinnacle is the sharpest oddsmaker in the world, known for booking the largest wagers. Hence, whenever DraftKings or FanDuel differ from Pinnacle, I typically side with the latter. 

I used this approach when successfully betting the Anatomy of a Fall to win Best Original Screenplay at the 2024 Academy Awards. The Anatomy of a Fall's odds were -280 at DraftKings but -501 at Pinnacle. 

Lastly, Baker won "Outstanding Achievement in Feature Film" at the 2025 Directors Guild of America Awards. Nineteen of the previous 21 winners of this award have also won Best Director at the Oscars, including the last four Academy Awards. 

Best Film Editing: ‘Conclave’ (-165) 

This is another category where DraftKings differs from Pinnacle. Conclave is the odds-on favorite at both sportsbooks. However, at DraftKings, the Vatican thriller is -165 compared to Pinnacle, where it's priced as a heavier favorite, -210. The last two Best Picture winners also won Best Film Editing. But, from 2013-2021, the Best Picture winner did NOT win for editing. 

Plus, the Best Picture category is more wide-open than in previous years. Meaning, other films will get recognition in these overall production categories. Finally, people will see Anora's Best Film Editing odds at +175 and its Best Picture odds at -250, and think they are getting value in the former. Well, that's a "sucker bet" if there is such a thing at the Oscars. 

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