Entertainment
8 Worst Movies That Won Multiple Oscars
Sometimes, a movie that people would have preferred went home without any prestigious awards instead end up snatching not just any award, but an Oscar, almost inarguably the single most prestigious award in the film industry. On a few rarer yet sadder occasions, a film gets to take not just one Academy Award home, but multiple. Typically, when a movie wins two or more Oscars, it’s a sign that it’s at least decent; but there are some that defy that rule.
From films that are so mediocre that they just barely count as “bad,” such as The Iron Lady; to ones that are almost universally panned, like Emilia Pérez, there are thankfully only a handful of low-tier films which have won more than one Academy Award. That handful, however, is nonetheless a stain on the history of an awards ceremony that has otherwise been somewhat successful at only rewarding films that are at least solid.
8
‘The Iron Lady’ (2011)
Setting aside the fact that Margaret Thatcher is not exactly one of the most universally-loved historical figures of modern times, making a biopic based on her life and work an inherently divisive concept, The Iron Lady is still not a good movie in any sense imaginable. With its 51% score from both critics and audiences on Rotten Tomatoes, it’s one of the lowest-rated Oscar-winning movies on the platform.
That hate is well-deserved. The film won a well-earned Best Makeup and Hairstyling Oscar, but it also represented Meryl Streep‘s third-ever Academy Award victory, for a performance that low-key deserved a Razzie nomination instead. Her take on Thatcher feels more like a cartoonish impersonation than a true embodiment of such a complicated woman, but it’s not like the script gave her much to work with, anyway. There’s no depth or political analysis in this shallow, awfully boring biopic melodrama that sacrifices creativity in the name of pandering to the Academy.
7
‘One Night of Love’ (1934)
Since cinema was still such a remarkably young medium at the time of the Academy Awards’ creation in 1929, and Academy voters were only starting to figure out which kinds of films deserved Oscars and which ones didn’t, there were many award winners from the 1930s which have aged poorly. Case in point: the romantic musical One Night of Love, one of the worst Oscar-winning movies of all time.
There’s some merit to a few of the tunes of this grand opera-like musical, but these musical segments struggle to carry a story that’s so clichéd, so predictable, and so awfully dated in virtually every way. The movie won Best Sound Recording and the first Best Original Score Oscar ever, both of which were deserved-enough wins. But the film overall has lost all of its luster and magic as the years have passed, today standing as nothing more than a star vehicle for Grace Moore and her admittedly legendary singing talent.
6
‘Anthony Adverse’ (1936)
As if any more proof were needed that the ’30s arguably had the highest concentration of Oscar-winning films that have aged awfully, there’s also Anthony Adverse, one of the decade’s most hated Hollywood movies nowadays. Clocking in at nearly two-and-a-half hours, this epic is based on the 1933 historical epic book of the same name by Hervey Allen, though it’s an epic in name only. Thanks to its lifeless story and disjointed pacing, it holds an 18% rate of approval from critics on Rotten Tomatoes. There are those who would argue it deserves even less.
Trying to cram such a massive 1,200-page epic novel into a single film was always going to be a difficult task to succeed at, but director Mervyn LeRoy found ways to fail in surprisingly spectacular fashion still. The whole film feels painfully rambling and episodic, like a cinematic CliffsNotes summary of the book without any of the heart, emotion, or complex character arcs.
5
‘Wilson’ (1944)
Throughout history, there have been some biopics based on the lives of famous United States Presidents which have been genuinely great films. Wilson, the Woodrow Wilson biopic, is not one such movie. Starring character actor Alexander Knox in one of the few leading roles that he ever played, the film had such an unusually high budget that it inevitably ended up becoming a box office disaster.
Even still, it made its way to a whopping five Academy Awards, including Best Cinematography and Best Original Screenplay. Technically, it’s a strong enough film; but clocking in at two and a half hours and offering pretty much no entertainment value for anyone who’s not a hardcore fan of the history of US Presidents, it’s a bit of a chore to sit through. Poorly paced, hugely propagandistic, and with even less political nuance than The Iron Lady, it’s one of the most awfully boring films ever to win so many Academy Awards.
4
‘Crash’ (2004)
At this point, Crash has become such an infamous movie that you’d be hard-pressed to find anyone who watched it and didn’t dislike it, or anyone who hasn’t watched it and is somehow willing to. It’s one of the Best Picture Oscar winners that have aged like milk the most, a movie whose heavy-handed message boils down to nothing more complex than just “racism bad.” It’s the sort of drama whose themes could be put on a poster without dumbing them down any further.
And yet, in spite of its painful lack of subtlety, the Academy just ate Crash up. Aside from Picture, it also won Best Editing and Original Screenplay, all three wins being among the most puzzling of the 21st century thus far. There are some solid performances here that at least make the film somewhat tolerable, but as the years have passed, Crash has only gotten worse with age.
3
‘Cavalcade’ (1933)
Based on Noël Coward‘s stage play, Cavalcade is a decades-spanning period epic which was an overwhelming critical and financial success upon release. As the years have passed and audiences’ preferences and sensibilities have shifted, opinions on this winner of three Academy Awards have only gotten less favorable. All in all, it’s one of the most disappointing Best Picture wins of all time, one of those duds that Oscar completionists have to painfully sit through in order to fulfill their ambition of watching every Best Picture winner ever.
In many ways, one can attribute the terrible way in which Cavalcade has aged to its being an adaptation of a play. In its efforts to conserve the theatrical spirit of the source material, its melodramatic story ends up feeling unbearably saccharine while its subpar performances feel stiff by comparison. Add to that a dated romantization of the British Empire and social inequities, and you get a film that has aged just about as poorly as any Best Picture winner possibly could.
2
‘Cimarron’ (1931)
The 1930s saw several terrible films claw their way to Oscar glory, but out of all the ones that managed to earn two or more Academy Awards, Best Picture winner Cimarron is easily the worst. If one where to rank every Best Picture-winning Western, this one would have to be at the very bottom. Tonally uneven and filled to the brim with offensive racist stereotypes, it’s a testament to every dimension of the Western genre that has become thematically problematic in retrospect.
But even if it weren’t racist—which it is—, Cimarron would still feel like an awfully archaic disaster by modern standards. Its pacing is glacially slow, its protagonist is deeply unlikable, its celebration of colonialism is repulsive, and its overwhelmingly serious tone makes it pretty much impossible to enjoy any substantial parts of it. Cimarron must have seemed like a tremendous achievement back in 1931, but it has been almost a century since then, and audiences have come to demand infinitely better Best Picture winners.
1
‘Emilia Pérez’ (2024)
One would have had to live under a rock throughout the entirety of the 2024-25 awards season in order to not have heard something about the infamous Emilia Pérez. Awfully racist, awfully transphobic, and awful in virtually every way imaginable, this is one of the worst musical movies in history, even in spite of the fact that it made its way to a record-breaking 13 Academy Award nominations. Thankfully, it only won two of those.
But even still, if the world were any fairer of a place, Emilia Pérez would have had to be content with only a few Razzie nominations. Alas, the Academy found its shallow commentary on gender roles and thinly-researched critique of organized crime in Mexico (made by a French filmmaker with next to zero knowledge of the actual situation) absolutely irresistible. Never has a decision to award any film with multiple Oscars been this objectionable.
Emilia Perez
- Release Date
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November 13, 2024
- Runtime
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130 Minutes
- Director
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Jacques Audiard
- Writers
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Jacques Audiard, Thomas Bidegain, Léa Mysius
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