Betting the Academy Awards can seem like a daunting task, but it’s an event that has just as many upsets as a horse race. In that regard, the best way to handicap the Oscars is looking at it as you would look at the Kentucky Derby and the Kentucky Derby prep races.
Here is how I’m handicapping this year’s Academy Awards:
As of March 16, The Power of the Dog (-280) is the favorite here. The odds for the two contenders behind it are the surprise award season ensemble-driven CODA (+ 400) and Belfast (+ 650), the black-and-white gem out the United Kingdom.
The Power of the Dog has continued its dominance, winning at the Golden Globes, Critic’s Choice and the all-important British Academy Awards. In my opinion, you should never bet anything chalkier than -125 in the Oscars because like the Super Bowl, there are so many ways to bet this event.
Typically the British Academy of Film is a good place to look when it comes to Best Picture and Best Actor, and Power of the Dog won Best Picture at both the British Academy and Critics Choice Awards.
This category is always susceptible for upsets, although I don’t see it happening this year with Power of the Dog moving with the momentum of a freight train. If I had to bet on an upset, I would go with Belfast (+ 650) as it hits on many of the notes that the Academy has voted on before: It’s a period piece and it shows a slice of life through the eyes of a child during a turbulent time in Northern Ireland/Ireland relations. Also watch out for CODA (+ 500) which has been the darling of the award season and is campaigning hard in the lead up to the Oscars.
BEST SUPPORTING ACTOR
Speaking of CODA, the one award I believe they will certainly win is in the Supporting Actor category with Taylor Kotsur (-330). The early-season favorite was Kodi Smit-McPhee (+ 200) for The Power of the Dog. He won early at the Globes, but as the season has progressed Kotsur has really taken the reins in this category. If you’re looking for an upset, it could be in this category with Smit-McPhee taking home the statue.
BEST SUPPORTING ACTRESS/ BEST DIRECTOR
This will be a brief analysis: Don’t bet these two categories.
The winner for Best Supporting Actress is going to be Ariana DeBose (-1600) from Steven Spielberg’s adaptation of West Side Story. She has won every award this season -- and deservingly so. If you wanted to try to pick an upset here go with Kirsten Dunst (+ 600) from The Power of the Dog.
Best Director is going to The Power of the Dog director Jane Campion (-3500). Kenneth Branagh (14-1) for Belfast maybe has an outside shot, but I wouldn’t recommend playing that here.
Will Smith (-800) has won many of the big awards at the SAG’s, Globes and Critic’s Choice Awards for his portrayal of Richard Williams, the father/coach of the Williams sisters in King Richard. This looks to be his year, and if you want to call it a career Oscar win, then go ahead. Every year there is one big surprise at the Oscars, though, and it could come in this category with Benedict Cumberbatch (+ 450). His role is big and somewhat understated, and the Academy loves to reward a role that requires restraint and either a physical or emotional change. I think Will Smith is a rightful big favorite, but don’t be surprised if Cumberbatch makes a late push.
In one of the most competitive fields this year, Best Actress is really down to four contenders. The favorite right now is Jessica Chastain (-150) for The Eyes of Tammy Faye, in which she also served as producer. After losing at the Golden Globes to the next short shot on the board Nicole Kidman (+ 250) in Being the Ricardos, Chastain has swept every award show, winning at the SAG’s and Critic’s Choice Awards. How did she do at the British Academy’s? She wasn’t nominated along with all the other nominees for this year’s Oscars, so we can’t use that as a measuring stick.
I really liked Nicole Kidman in Being the Ricardos and think it's the type of showy performance of a beloved American Icon that could steal this award. Look no further than Renée Zellweger’s performance in Judy where she basically rode the Over the Rainbow train to her golden statue.
Even though she hasn’t made much noise this award season, Kristen Stewart (+ 500) has a shot to make a splash on the big night for her frightening look as Princess Diana in Spencer. She is great in the role, it helps that she is the clear-cut star in this picture. It must be mentioned that anything that is connected to Princess Diana always will gain attention, including the actress who plays her. Watch for her to make some noise leading up to March 27.
Olivia Colman is + 500 for Lost Daughters. She has become a favorite of the Academy winning in 2018 for The Favorite and being nominated last year for The Father. Penelope Cruz (16/1) is nominated for Parallel Mothers, which may appeal to the international voters (a growing part of the Academy), but realistically she doesn’t have a shot against this field.
BEST OF THE REST
Some of the long shots I feel are being overlooked are in the below the line categories.
Best Makeup and Hair Styling: Cruella (+ 500)
Best Original Screenplay: Belfast (+ 175)
Best Original Song: Dos Oruguitas (Encanto) (+ 225)
Best Film Editing: The Power of the Dog (+ 300)