Wilson’s Oscar Betting Picks & Predictions: Best Picture, Best Actress, More Academy Awards

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VALERIE MACON/AFP via Getty Images

  • Collin Wilson first started an Oscars pool in high school. Over the past three decades, he's honed his handicapping skills.
  • See Wilson's favorite bets for some of the most anticipated awards on Sunday night.

It was March 1995 when I decided to run my first Oscars pool. I was a senior in a small town Arkansas high school, but I was positive the hundred bucks in my pocket could turn into a thousand backing one horse in the race. The 67th Academy Awards featured films such as Pulp Fiction, Four Weddings and a Funeral, Forrest Gump and Shawshank Redemption.

While Forrest and Jenny would turn out to be a generational story, my horse was based on a Stephen King novel with a lifetime performance from Morgan Freeman. Shawshank Redemption had a theatrical re-release and was becoming a dark horse to sweep the seven categories in which it was nominated.

My high school Oscars pool was set and not a single soul went for Shawshank Redemption. Much like the prison cast from the movie, I spent an entire week chanting ‘fresh fish’ at my classmates. Soon after David Letterman’s ‘Uma, Oprah’ joke bombed, so too did my Shawshank money.

Fast forward 25 years later, Shawshank Redemption is considered the greatest movie of all time. My pockets may have been empty heading into senior year spring break, but it did not deter me from betting on this event yearly.

2020 Oscar Odds

Much like odds on a WWE event, numbers can change drastically for nominations in each category. Unlike a WWE event or other guild award shows, there are no leaks from the Academy Award winners. Steam on a nominee can be the result of expert opinion or make believe rumors intended to move a line.

Ask anyone who bet Yorgos Lanthimos last year how much to bet on rumors.

Best Actor, Best Supporting Actress, Best Director and Best Cinematography all have heavy favorites and should be added to a parlay card. This column will serve as a glimpse into the categories in which I have doubt on the current betting favorite.

Here’s a list of the underdog nominees I like along with my betting strategy in those categories.

Oscar Betting Picks & Predictions


Odds as of Tuesday and via DraftKings, where Action Network users can get 10-1 odds on any nominee to win Best Picture. New Jersey and Indiana only.


Best Makeup & Hairstyling

For those of you unaware, there is a Makeup & Hairstyling Guild Awards. This year saw Bombshell win ‘Contemporary Makeup’ and Joker win ‘Period/Character Makeup.’

The past six Oscar winners have aligned with MUAHS winners, but historical trends point to an advantage for Joker.

Per Oscarmetrics — a book that examines whether statistical trends can be used to predict Academy Award winners — the Best Makeup and Hairstyling award tends to go to the film with more overall nominations than the average total nominations of its competitors. Simply put, the more a movie shows up in other categories the better chance of winning here.

The reasoning for this has nothing to do with makeup or hair. Many of the academy voters tend to choose their favorite movie across the board. Other voters choose to honor a film with an less distinguished category. Since the categories creation almost 40 years ago, 70% of the winners have had the most cumulative nominations.

Bombshell, Judy and Maleficent have a combined six nominations. Joker and 1917 are in the double digits, well ahead of the 5.4 average nomination size. Joker is the only film in this group nominated for Best Costume Design, an indicator of the winner more than 50% of the time.

Pick: Joker +550 (down to +200)

[Bet now at DraftKings]

Best Costume Design

This category all depends on the Costume Designer Guild Awards, which have been accurate on nominations and wins over the past five Academy Awards. It is worth mentioning that Little Women, the Oscar favorite, was not even nominated at the guild awards.

At the CDG Awards, Jojo Rabbit won for Period Film, Knives Out for Contemporary Film and Maleficent for Fantasy Film. With only Jojo Rabbit nominated for the Academy Award, the underdog Hitler Youth movement picture deserves the look.

Pick: Jojo Rabbit +275 (down to +100)

Best Documentary: Short Subject

There are no previous trends or analytics supporting Superman, I just have a hunch that this short documentary will generate plenty of buzz among voters. St. Louis Superman looks at an activist in Ferguson, Missouri who is elected to the state House of Representatives. Gun violence in the Ferguson area along with the death of the main characters brother at 9 years old leads straight to the House floor in Washington.

Learning to Skateboard in a Warzone is a worthy story to tell, but the critics have started to generate buzz for Superman. Of the 9,000-plus voters, domestic gun violence is a hot topic for the liberal voters.

Pick: St. Louis Superman +1000 (down to +200)

[Bet now at DraftKings]

Best Original Score

1917 (+325)

Joker should absolutely be the favorite in this category, as Hildur Guðnadóttir has become the hottest name in the industry. Guðnadóttir just won the Best Score Grammy for her work on Chernobyl and was named Composer of the Year at the World Soundtrack Awards.

The money on 1917 Best Original Score completely pulls at the ‘lifetime achievement’ strings. Thomas Newman is nominated once again by the Academy but is yet to win a single instance. Newman has 15 nominations over his career for work including Shawshank Redemption, American Beauty, Finding Nemo and WALL-E.

There certainly is a bit of Meryl Streep to this story. The actress has 17 nominations for Best Actress and just two victories. Newman may get enough votes for ‘lifetime achievement’ to make this category interesting.  Personally, I will wait for the number to offer better odds as the public gets more involved in the market.

Pick: 1917 +325 (will wait for +500)

[Bet now at DraftKings]

Best Actress

While every expert at Gold Derby had Glenn Close projected as the 2019 winner, it was Olivia Colman who took home the award — another reminder that the Academy is becoming more unpredictable as nominee and voter base sizes continue to grow.

While Renée Zellweger is sweeping SAG and the Golden Globes, the big question is if an underdog can win this category. The answer is absolutely.

Per Oscarmetrics, two trends have been constant with the award winners in Best Actress. First, play a historical character. Both Zellweger and Cynthia Erivo accomplish that in their respective roles.

The second has to deal with age.

The Best Actress award has seen a large majority of it’s winners go to the 35 and under crowd along with the 60-plus. Marlee Matlin, Jennifer Lawrence and Audrey Hepburn all won at an early age while Helen Mirren, Meryl Streep and Jessica Tandy won post 60.

Cynthia Erivo of Harriet just turned 33, indicating a 23% win probability. Six former winners were 33 years old.

Zellweger is trying to overcome the steepest of odds in a category that dates back to 1927. The actress is 50 years old, which is in the range for the lowest win probability for the category. No person has ever won the award between the ages of 50 to 53, while only two have won the award between the ages of 50 through 59.

Pick: Cynthia Erivo +2500 (down to +500)

[Bet now at DraftKings]

Best Picture

This is the most unpredictable category by far, as three of the past 15 years have produced the biggest upsets.

Moonlight is considered the biggest upset of all time after coming up empty for Best Picture at BAFTA, SAG, Directors Guild and Writers Guild. Plenty of people point to the increase in number of nominees and the additional diversity in the voting base.

As a gambler, we couldn’t be happier that long shots are getting to the window.

The rules for beating the average nomination size apply to this category, as Annie Hall is the only Best Picture with a score of -1.6. The average nomination score for 2020 is 7.66, knocking out every contender except The Irishman, 1917, Joker and Once Upon a Time in Hollywood. While 1917 is my personal favorite, I would not wager on them with the current odds.

1917 is attempting to be the first Best Picture without a nomination in Best Acting or Best Film Editing since 1934, the birth of the editing category. If voters are not into 1917, the lack of dialogue between two main characters in a straight-forward story without a nomination in editing would be the reason.

Parasite may also have a tough path as a foreign-language film. No picture has ever won Best Foreign Film and Best Picture, something Parasite will obviously have to defeat. The movie also has a very low number of total nominations, something that would eclipse Annie Hall’s mark of -1.6.

As my colleague Chris Raybon pointed out on the Action Network Podcast, there are voters who refuse to watch movies with subtitles.

The voting process for Best Picture is very important from a betting standpoint: A film must have a required number of first place votes, then garner enough overall votes to win. An Academy Award voter ranks the films for Best Picture and does not simply check a box.

A movie can simply garner a few first-place votes then sweep second- or third-place votes on the majority of ballots to win Best Picture.

This is truly a ‘movie I hated the least’ voting scenario. Both Joker and Once Upon A Time In Hollywood meet the grand slam nominations for writing, directing, acting and editing. Neither film will be downgraded for a lack of dialogue, editing or as a foreign film.

Parasite and 1917 leave lasting memories and should be a two horse race for Best Picture, but because of the voting process, this is a four-horse race. I will take any of the four horses that offer the best odds.

Picks: Joker +800; Once Upon A Time In Hollywood +1200 (and any outlet with backslide steam on Parasite or 1917 to +400)

[Bet now at DraftKings]

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