Winning an Oscar is supposed to be the ultimate validation of cinematic excellence. But history has shown that even the Academy of Motion Picture Arts and Sciences can have an off day—or an entire awards season. Some films have managed to snag multiple golden statuettes despite being, well, pretty terrible. Whether they're boring biopics, heavy-handed dramas, or dated musicals, these movies make you wonder if the voters were watching the same screen as the rest of us.
From the infamous Crash to the recent Emilia Pérez, here are the worst films that somehow walked away with more than one Oscar.
8. The Iron Lady (2011)
Meryl Streep is a national treasure, but even she couldn't save this muddled biopic about Margaret Thatcher. While the makeup and hairstyling Oscar was well-deserved, Streep's third Academy Award for Best Actress felt more like a lifetime achievement nod than a recognition of a great performance. Her portrayal veers into caricature, and the script offers zero political insight or emotional depth. With a 51% score on Rotten Tomatoes from both critics and audiences, it's one of the lowest-rated multiple-Oscar winners in history.
7. One Night of Love (1934)
In the early days of cinema, the Academy was still figuring things out. This romantic musical won the first-ever Best Original Score Oscar and Best Sound Recording, but the film itself has aged like milk. The opera-like tunes are pleasant enough, but the clichéd, predictable story is a slog by modern standards. It's a relic that only survives as a showcase for Grace Moore's singing talent.
6. Anthony Adverse (1936)
Based on a 1,200-page novel, this epic historical drama tries to cram too much into its nearly two-and-a-half-hour runtime. The result is a disjointed, lifeless mess that holds an 18% critic score on Rotten Tomatoes. Director Mervyn LeRoy fails to capture any of the heart or complexity of the source material, leaving viewers with a cinematic CliffsNotes that feels more like a chore than entertainment.
5. Wilson (1944)
This Woodrow Wilson biopic was a box office disaster despite its massive budget, yet it somehow won five Oscars, including Best Cinematography and Best Original Screenplay. Technically competent but painfully boring, the film is a two-and-a-half-hour propaganda piece with zero political nuance. Unless you're a die-hard fan of presidential history, this is one of the most tedious multiple-Oscar winners ever.
4. Crash (2004)
Perhaps the most infamous Best Picture winner of the 21st century, Crash is a textbook example of a movie that mistakes heavy-handedness for profundity. Its message—'racism is bad'—is delivered with all the subtlety of a sledgehammer. Yet the Academy awarded it three Oscars: Best Picture, Best Original Screenplay, and Best Editing. It's a film that has aged so poorly that even its defenders have mostly gone silent.
3. Cimarron (1931)
This Western epic won three Oscars, including Best Picture, but modern audiences find it nearly unwatchable. The pacing is glacial, the performances are stilted, and its portrayal of Native Americans is cringeworthy by today's standards. It's a historical curiosity that proves even the Academy's early choices could be wildly off the mark.
2. Emilia Pérez (2024)
The most recent addition to this dubious list, Emilia Pérez is a musical crime drama that critics have called 'a trainwreck' and 'almost universally panned.' Despite its multiple Oscar wins, including Best Original Song and Best Supporting Actress, the film is a chaotic mess that fails to cohere. It's a stark reminder that even in the modern era, the Academy can still get it spectacularly wrong.
1. The Broadway Melody (1929)
The second-ever Best Picture winner is a musical that has not aged well at all. Its simplistic plot, dated performances, and technical limitations make it a slog for contemporary viewers. Winning an additional Oscar for Best Director, it's a film that only survives as a footnote in cinema history—and a cautionary tale about the dangers of early Academy hype.
These films serve as proof that even the most prestigious awards can be handed out for all the wrong reasons. Whether it's a misguided attempt at relevance, a love for a star performance, or just a collective lapse in judgment, the Academy has a long history of rewarding mediocrity. Next time you see a movie win multiple Oscars, remember: it might just be one of these.
