Tomorrow, we will be celebrating the best movies of 2025 as the 98th Academy Awards take place at the Dolby Theatre in Los Angeles. Led by Ryan Coogler‘s record-breaking nominee, Sinners, and director Paul Thomas Anderson‘s critical darling One Battle After Another, the stage is set for the biggest prizes in the movie calendar to be handed out.
Ahead of this year’s Oscars, thoughts turn to those movies of the past that cemented their names in cinema history with Academy Award victories. However, for every iconic winner, such as The Godfather or<em> Parasite</em>, others have found notoriety for all the wrong reasons, as they take the place of another movie or performer widely considered the more deserving nominee or winner. With that in mind, here’s a look at those Oscar mistakes that have aged like milk.
Mickey Rourke – ‘The Wrestler’ (2008)
The race for the Best Actor prize was one of the most intense in the Academy’s history. Although other performances that year were impressive, it eventually came down to a nail-biting contest between Sean Penn‘s transformation into Harvey Milk and Mickey Rourke‘s performance as Randy “The Ram” Robinson in The Wrestler.
The decision to award Penn the prize on the night wasn’t necessarily an upset, but, years on, and the comeback story of Rourke in a performance that mirrored his life has stood the test of time. The best performance in Rourke’s career, compared to a performance that doesn’t even come close to Penn’s best, this was a mistake by the Academy.
Toni Collette – ‘Hereditary’ (2018)
The horror genre may have a greater presence at the Academy Awards than ever before, with films like Get Out and The Substance breaking into the Best Picture category, but that doesn’t mean it is still not often disrespected. Perhaps the most egregious modern case in point is Toni Collette‘s snub from the Best Actress category in 2019.
One of the best leading female turns in modern memory, few have managed to conjure a visceral, ground-shaking performance quite like Collette’s in Hereditary. A highlight of the recent horror renaissance, the film might have its detractors, but most would consider it a masterpiece, and one that deserved greater critical recognition.
‘Singin’ in the Rain’ (1952)
It’s true that audiences in 1952 didn’t quite take to Singin’ in the Rain as future generations would. A modest box office success, the movie would go fairly overlooked by critics, too, although it did pick up a pair of Academy Award nominations for Best Score and Best Supporting Actress for Jean Hagen.
Now considered one of the greatest musical movies of all time and a quintessential piece of Golden Age cinema, Singin’ in the Rain‘s omission entirely from the Best Picture line-up at the 25th Academy Awards is shocking. This shock is compounded when considering that year’s winner, The Greatest Show on Earth, is one of the worst picks in Oscars history.
‘Saving Private Ryan’ (1998)
One of the most famous snubs of all time, the victory of John Madden’s Shakespeare in Love at the 71st Academy Awards changed the way Oscars campaigns were run forever. Gone was the reliance on a film’s quality, and aggressive marketing campaigns, and quiet slander of competition became the norm. Truly, Shakespeare in Love did not deserve to win that night.
This is made all worse when considering it defeated Saving Private Ryan, one of the greatest war movies ever put to film. Steven Spielberg’s unflinching masterpiece should’ve walked away from the ceremony with the most prestigious prize, but at least it still took home a total of five Golden Statues.
Ralph Fiennes – ‘Schindler’s List’ (1993)
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No decision by the Academy has aged this poorly. At the 62nd Academy Awards, Driving Miss Daisy took home the Best Picture prize despite its sanitized depiction of race relations in segregated South. A film that made many uncomfortable, its triumph raised more than a few eyebrows as a precursor discourse decades before #OscarsSoWhite campaign began.
What makes this decision even more painful is that Spike Lee’s groundbreaking Do The Right Thing was an unflinching portrayal of how racism was manifesting on American streets only for it not even to make it into Best Picture nominees list. Driving Miss Daisy’s win has aged terribly, but Do The Right Thing’s snub has aged even worse.
