2021 Oscar Predictions: Trial of the Chicago 7 For Best Picture & More

After a very long wait, the winners for the 93rd Academy Awards will finally be crowned on Sunday.

In anticipation of the biggest night in Hollywood, our staff members are celebrating the only way they know how — by betting. Find their favorite picks for the 2021 Oscars outlined below.

All odds as of April 24 and via DraftKings.

2021 Oscar Predictions

Best Picture: Trial of the Chicago 7 (+600)

Katie Richcreek (editor): Nomadland is the rightful favorite, but at -670, its odds give the film an 87% implied probability of winning Best Picture. And even with historical trends on its side — including nominations for Best Director, Best Adapted Screenplay and Best Film Editing, as well as precursor wins such as Best Film at the British Academy Film Awards — an 87% implied probability is too high.

The primary argument is that two key changes to Oscar voting have led to more volatile results over the past 11 years:

1. The Academy adopted a preferential ballot for Best Picture for the 2009 cycle, meaning that instead of selecting one winner, voters rank nominees. As a result, less polarizing films that don't necessarily garner many first-place results, but are otherwise high on many voters' ballots have an edge.
2. The body of voters has grown about 50% since 2015 following #OscarsSoWhite (based on numbers reported by Variety), meaning that they've increasingly strayed from historical trends.

According to Oscarmetrics author Ben Zauzmer, between 1933 and 2011 (aka three cycles into preferential voting for Best Picture), 78% of Best Director winners went on to win Best Picture for the same film. Over the past eight years, though, only three (37.5%) of Best Director winners have also taken home Best Picture.

With Chloé Zhao an even heavier favorite to win Best Director at -3335 (97.1% implied probability) for Nomadland, I'm more inclined to believe she's a lock to win that award, and less inclined to believe Nomadland will be the film to buck recent trends in favor of older ones.

The Trial of the Chicago 7 could be the beneficiary of this recent trend, not only because preferential balloting arguably favors films that are more generally liked vs. overwhelming adored, but because it won Best Ensemble at the Screen Actors Guild Awards (SAGs) — a trait shared with past Best Picture winners that upset consensus favorites of their respective years.

Since the SAGs introduced the award in 1995, there have been nine times that Best Director winners at the Oscars haven’t also won Best Picture, and five of those nine upsets were pulled off by films that had previously won Best Ensemble. (Spotlight was the most recent example of this five years ago.)

So, while Nomadland is more likely to win, I see betting value on The Trial of the Chicago 7 at +600 odds.

Best Actress: Frances McDormand +400

Jeremy Pond (editor): This might be the most wide-open major category we’ve seen in a long time, with four of the five nominees priced at +600 or lower on the odds. Carey Mulligan (Promising Young Woman) is the current favorite at +125, with former Oscar winner Viola Davis next at +200 for her performance in Ma Rainey’s Black Bottom.

However, the underlay in this battle is Frances McDormand, who starred in massive Best Picture favorite Nomadland (-670). McDormand is a six-time nominee, winning two Best Actress awards for her work in "Fargo" (2016) and Three Billboards Outside Ebbing, Missouri in 2019. A win this year would make her a perfect 3 for 3 in the category.

McDormand’s performance in Nomadland was simply brilliant. She plays a woman named Fern, who travels the country following her husband’s death and becomes part of the nomadic life within America. This film is beautifully shot and directed by Chloé Zhao — oddsmakers have the rising Chinese star as a lock to win Best Director, with her currently sitting at -3335 odds.

For me, McDormand provides the best value among the top-four betting choices. She’s clearly someone the Academy voters love, having bestowed the golden man on her twice in the past five years in this category. The other intriguing angle on McDormand is the fact she went out and recruited Zhao for this film; not the other way around. That should resonate with voters due to the fact Zhao was obviously the perfect choice for job.

I played McDormand at a lower number a few weeks back, so I definitely grabbed her at +400 when she drifted up after the market moved toward Mulligan. That said, I don’t see the odds changing, but I’d take McDormand as low as +150 if there’s a shift prior to Sunday’s show.

Best Actress: Andra Day (+600)

Collin Whitchurch (editor): By far the most interesting of the major award categories, these odds have zigzagged all over the place and favorite Carey Mulligan's current price actually lists her at plus odds for the first time since early February. Shortly thereafter, she moved to -190 and has been around there until recently, when buzz for Viola Davis entirely changed the game.

Davis, whose performance as Ma Rainey was the best acting performing of the year across the board and absolutely deserves this award, didn't come out of nowhere. However, as recently as mid-March, she was tracking around the fourth-best odds, behind Frances McDormand and Andra Day, along with Mulligan. An honor by the Screen Actors Guild lowered her odds, but are complicated by the fact that the BAFTAs honored McDormand.

Further complicating things is the fact that Mulligan wasn't honored by either, and there's been only one time in history when the Academy Award Best Actress winner wasn't honored by either the SAG or the BAFTAs: 1994, which just so happens to be the first year of the SAG Awards, when the Oscar went to Jessica Lange (Blue Sky), the SAG Award went to Jodie Foster (Nell) and the BAFTA went to Susan Sarandon (The Client).

But wait, there's more.

Andra Day was awarded by the Hollywood Foreign Press Association for Best Actress (drama) at the Golden Globes. The Globes split their awards into two categories, of course, but the last time neither of the Globes Best Actress awards went to the actress who won at the Academy Awards was 2001, when Halle Berry won the Oscar for Monster's Ball while Nicole Kidman won a Globe for Moulin Rouge! and Sissy Spacek won one for In The Bedroom.

The other time that happened was in 1994, the same year the SAGs and BAFTAs got it wrong.

So to sum it up, Mulligan — the favorite — winning would mean the Academy Awards' Best Actress wouldn't have won at the SAGs, BAFTAs or Golden Globes, something that's only happened once and that was 27 years ago.

Given all the chaos, the best advice I can give is to close your eyes and throw a dart. Or, in reality, take a flier on the most appealing odds among the four contenders (while pouring one out for Vanessa Kirby, who is very good in Pieces of a Woman).

That means a bet on Day at the time of this writing, but whichever of the four have the highest odds at the book of your choice at the time of your wager would work just the same.

Collin Wilson (analyst): Still reeling from an Erivo 50-1 bet that closed 12-1 in 2020, we take another crack at predicting Best Actress.

The formula provided a winner in 2020, and is tried-and-true method to cashing a ticket. The two biggest elements in determining a winner in this category is to play a historical character and the age of the nominee. For these five actors, the only historical characters are played by Viola Davis and Andra Day.

The average age of the winner in the Best Actress category is generally lower than 35 and greater than 60. Zellweger was only the third woman to ever win the award between the age of 50 to 59 years old. Davis falls into the neutral territory at 55 years of age, with McDormand at 63 years old and the remaining candidates 36 and under.

In past years when there were two nominees who played historical characters, the expectation is a victory 40% of the time. That actual number is 47% since the award was first given in 1929. The analytics point to an upset here with Andra Day, but splitting a unit with Davis is a solid backup plan.

I would bet this down to +150 odds.

Best Original Screenplay: The Trial of the Chicago 7 (+275)

Whitchurch:In both screenwriting categories, it's important to keep in mind that the Academy's qualifications are much different from the Writer's Guild of America's top prizes. Every year, the WGA's nominations leave out several Oscar contenders that were not written by guild members, and this year's list included Nomadland, Mank, Minari and more.

That said, it's tough to argue with Promising Young Woman as the strong favorite. The BAFTAs have a so-so predictive record (12 of the last 20 correct) and Promising Young Woman emerged victorious there over The Trial of the Chicago 7. Although it's important to note that the BAFTAs drastically overhauled their voting process this year, so even that track record is tough to fully figure.

I think this is where Promising Young Woman gets rewarded where it's going to fall short in most of the bigger categories (unless Mulligan pulls out Best Actress), but I can see an argument for The Trial of the Chicago 7. The Academy loves Aaron Sorkin. Well, it at least loves to nominate him, at least. And a loss here would make him 1-for-4 in screenwriting nominations.

This category is right in line with where we often see upsets, though, so I'm recommending a play on Sorkin's Trial down to +200. Minari is the toughest to figure, so my recommendation there is to watch for movement and if you see the odds start to shorten, jump before they get to short.

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Best Original Screenplay: Minari (+1400)

Wilson: This is a tricky category because of the rules that follow the analytics. The Writers Guild winner generally follows up with an Academy Award.

That is good news for Promising Young Woman — winner of the Writers Guild Original Screenplay over The Trial or the Chicago 7, Sound of Metal and Judas and the Black Messiah. But the movie missing from that list is Minari.

Due to restrictions, Minari was ineligible to be nominated at the Writers Guild, making the nominee a complete wildcard. The movie did pull six nominations from the BAFTA's and 10 from the Critics Choice Awards. If there is an ace in the hold, it may be Lee Isaac Chung filling the role of writer and director.

Writing from life experiences and directing is what got Almost Famous and Moonlight to the window.

OSCARmetrics predicts a 12% chance for a Writers Guild ineligible entry to defeat other nominees that were up for the WGA, while the favorite is 67%. The correct odds for Minari should be +700 and Promising Young Woman at -200. With those buy prices, Minari is the pick, but keep an eye out for steam and a cheap buy on the clubhouse leader.

I would bet this down to +700.

Best Adapted Screenplay: The Father +300

Chris Raybon (analyst): Nomadland has its strengths, but I’m not sure a deliberately plotless screenplay should be considered a lock. The Gold Derby editors agree: 91% are on The Father; not Nomadland. The Father‘s expert odds also imply a 51.5% chance of winning after a late surge, so there’s major value here.

I would bet The Father all the way down to -105.

Best Visual Effects: The Midnight Sky +275

Eugenia Leal (product analyst): If there's going to be an upset on Sunday, it will be with The Midnight Sky for Best Visual Effects.

This movie starring George Clooney illustrates the complex exploration of space, as scientists go off in search of a habitable planet while their Earth is imploding. From Earth, to space, Jupiter and beyond, The Midnight Sky captures gorgeous visual effects only seen in movies like the Martian and Interstellar. In 2015, Interstellar won this award for taking their audience through an incredible voyage through space and time.

The Midnight Sky achieved this with breathtaking scenes and realism throughout the film. Compared to your classic action movie like Tenet (-560), and Mulan (+1700), The Midnight Sky is different from the rest because it takes on the task of illustrating a journey through space that is both realistic and captivating.

As a +275 underdog, a $100 bet would net a $275 profit.

Best Animated Short: If Anything Happens I Love You -335

Pond: My lock on Oscars night comes via this 12-minute film that tells the story of grieving parents coping with the loss of their daughter, who was killed in a school shooting.

Directors Will McCormick and Michael Govier, who also wrote the film told entirely without dialogue, created this masterpiece that's shot in 2D animation and was created by an all-female animation team.

Obviously, the odds aren’t what you would describe as desirable. However, if you’re someone who has no issues laying this kind of number with a sizable investment attached, I believe IAHILY provides the best value of any of the big favorites in the prime categories.

At -335, the implied odds indicate it has a 77% chance of taking home the Oscar. So, according to our Betting Odds Calculator, a $100 bettor would profit $29.85 for a $129.85 return, a $1,000 wager would deliver a $298.51 profit, and so on.

Personally, I played IAHILY early on when the number was a tad lower, but tacked on more this week due to my belief it was better than the other four in the category. And if I’m being honest, I firmly believe it’s underpriced and should be going for north of -500 odds. All shorts have some sort of human element built into their respective stories, but IAHILY hits the deepest by addressing the sad reality of what’s becoming an American norm.

Lay the big odds — and take 12 minutes of your day — to watch this soon-to-be Oscar winner.

Best Original Song: Husavik +350

Raybon: Husavik is starting to gain steam and has gone from +400 to +355, while Speak Now comes down from -200 to -155 odds.

Husavik still a great value: Not only does its 28.5% expert vote handily beat out its implied probability, but it’s also considered the favorite among editors with 81.8% of the vote.

The experts and editors have been wrong only once each, so this should be treated as close to a toss up between Husavik and Speak Now. Io Si is getting more love from the markets than from Gold Derby, and only one film its had ranked outside the top two has won.

I believe Husavik has no worse than a 50/50 shot and would bet it down to +100 odds.