In the past two decades, an entire cottage industry of Oscar punditry has emerged online. As a result, for those “in the know,” the Academy Awards might feel more predictable than ever before. Still, every year there are a handful of true shockers, and these moments often become the highlight of the night.
That’s why, in celebration of National Underdog Day on Dec. 16, BetCalifornia.com is shifting from the many California sports betting updates and is shining a spotlight on the biggest Oscars upsets in recent years. Using SportsOddsHistory.com, we looked at the closing odds for all the eventual winners between 2010 and 2023 in each of the Oscars’ six major categories (Best Picture, Best Director, Best Actor, Best Actress, Best Supporting Actor & Best Supporting Actress). Then we ranked the 10 winners who had the longest odds before taking the stage and accepting their Academy Award.
Most Surprising Oscars Winners Since 2010
Colman & Hopkins: Oscars' Biggest Underdogs
February 24th, 2019 was supposed to be Glenn Close’s big night. The celebrated actress, who had never won an Oscar before, walked the red carpet into Hollywood’s Dolby Theatre wearing a gold dress that weighed in at 40 pounds. You can’t blame her for the symbolic (and presumptuous) gown. Vegas had set the odds of Glenn Close winning Best Lead Actress for her role in “The Wife” at -620. That suggests over an 86% chance of her taking home the Oscar.
But although Close was the favorite, it would be “The Favorite” that did her in — that is, the quirky international co-production about royal court life starring Olivia Colman as 18th-century British monarch Queen Anne. By the odds, Colman was +650 (representing a 13% implied probability), but she still managed to take home the Best Lead Actress Award. By the numbers, it’s the biggest Oscar upset in more than a decade.
Anthony Hopkins's 2021 win for “The Father” (which happens to co-star Olivia Colman) is the second biggest upset. He won at +600 odds. But it’s worth noting that Chadwick Boseman was an even bigger favorite than Close to win for his Leading Role in “Ma Rainey’s Black Bottom” — which was his final role before he tragically passed on Aug. 28, 2020.
Boseman was -1200 to win the Academy Award when the night began.
Other Major Upsets
Easily the most memorable upset on our list is 2017’s Best Picture win for “Moonlight,” which was a +430 underdog up against “La La Land,” a -450 favorite. The artful, queer coming-of-age story triumphing over the glossy musical would have been shocking in its own right — but, of course, the moment was punctuated by Faye Dunaway and Warren Beatty mistakenly announcing that “La La Land” had won. It turns out the adjudicators of the awards accidentally handed the envelope for Best Lead Actress to Dunaway and Beatty. That award of course went to Emma Stone for “La La Land.”
A pair of Best Director surprise wins also made that list at No. 7 and 8. First Boon Joon Ho’s 2020 win for “Parasite” (+310). The taut Korean thriller would also upset Sam Mendez and his “oner” WWI film “1917” in the Best Picture Category (+173)
And then all the way back in 2013, Taiwanese filmmaker Ang Lee won his second Academy Award for his visually arresting adaptation of the novel “Life of Pi” at +250 odds. Of course, this was the year in which “Argo” won Best Picture, but its director, Ben Affleck, didn’t even receive a nomination.
Legal betting on sports and the Academy Awards may not have arrived in California yet, but betting odds are still a great resource when filling out your office Oscar pool — just remember: don’t be scared of picking a few underdogs when California sportsbook apps become available.
Jeff Parker is an entertainment writer for BetCalifornia.com. A writer for film, television and the internet, Jeff is a life long movie buff, with a Masters Degree in Popular Culture. He lives in Halifax, Nova Scotia, where he works full time as documentary filmmaker and producer.