The 12 Worst Best Picture Oscar Winners Of All Time

The thing about the Academy Award for Best Picture is that it is a popularity contest. And, like most popularity contests, it rewards agreeability, both artistically — the winner must be a widely-liked crowd-pleaser, and institutionally — the winner must reflect well on the Academy. The archetype of the "Oscar bait" film is really just the mathematical derivation of decades of the Academy's membership defaulting to the films that pleased the most people while displeasing the fewest, always guided by a certain unspoken sense that Best Picture winners had to be prestigious and respectable — whatever that meant at any given point in history.

At some points, it meant terrible movies were rewarded with the exact right amount of cultural complacency to win Best Picture, whether because they were huge box office hits, because they flattered the industry's self-importance, or because they just fit too snugly into the reigning norms of "good taste." Whatever the case, here is a list of the 12 most preposterous laureates ever chosen in the Oscars' centerpiece category.

Adapted from the eponymous Edna Ferber novel and directed by Old Hollywood journeyman Wesley Ruggles, 1931's "Cimarron" chronicles several decades in the life of the Cravats, a family of settlers who move to an Oklahoma boomtown in 1889, and the various historical trials they go through at the turn of the 20th century.

Shockingly, "Cimarron" was the only Golden Age Hollywood Western — and, indeed, the only Western until "Dances with Wolves" in 1991 — to win Best Picture. And it's hard to imagine a worse representative for the genre. Nevermind the fact that the film is dreadfully, mind-numbingly boring, simply assuming that the audience will have an inherent, reverential fascination with the history-mirroring saga of the Cravat family instead of working to actually make it interesting; the true sin of "Cimarron" that's impossible to get past is its sheer racism.

The movie is even more hostile, patronizing, insulting, and demeaning than the norm for 1930s Westerns in its depiction of Native Americans; virtually every other scene features some sort of vilification, horribly dated notion, or ridiculous stereotype. And somehow, the fact that "Cimarron" is so polite and earnest makes the racism worse. Like the shoddiest Best Picture winners, it's a damning snapshot of what was once considered prestigious and agreeable in the American cultural mainstream.

A cynical bid for respectability by raunchy studio comedy specialist Peter Farrelly, this self-proclaimed 2018 biopic of Bronx bouncer Frank "Tony Lip" Vallelonga (Viggo Mortensen) and legendary concert pianist Don Shirley (Mahershala Ali) dramatizes the supposed camaraderie that blossomed between the two men when Vallelonga worked as Shirley's driver in a 1960s Deep South tour. That relationship is depicted in the kind of hokey, formulaic, "friendship beats racism" way that would look bad for a Best Picture winner released 30 years earlier, complete with hacky direction from Farrelly and the broadest, dumbest comedic caricatures you can imagine — but the film's problems don't stop there.

For starters, "Green Book" adds to Hollywood's long history of mishandling Black stories by completely disrespecting and disregarding Don Shirley, the actually relevant historical figure who lends the film interest, misrepresenting him so enormously that Shirley's family openly called out the movie's inaccuracy and fictitiousness. In effect, "Green Book" — a film co-written by Tony Lip's own son, Nick Vallelonga, who turned out to have made a highly offensive tweet against Muslims in 2015 — makes Shirley's story all about the white guy. Its true interest lies in celebrating Tony Lip, a man depicted as a lovable, kind, honest, streetwise goofball who, despite throwing out glasses used by Black handymen in the first five minutes, has plenty of life lessons to teach Shirley — including lessons about properly honoring his Blackness. The nerve of some filmmakers.

Director Frank Lloyd, who was one of the founders of the Academy of Motion Picture Arts and Sciences and its president from 1934 to 1935, made two Best Picture winners: First "Cavalcade" in 1933, and then "Mutiny on the Bounty" in 1935. The latter, while not transcendental, is at least a solid seafaring good time with strong performances. "Cavalcade," meanwhile, is one of those Best Picture winners that make you wonder what the heck voters at the time were thinking.

Truth be told, it's not quite so hard to take a guess: "Cavalcade," a Noël Coward adaptation about the life of an upper-class English family throughout the first three decades of the 20th century, is the kind of agonizingly respectable, painfully tasteful, and utterly dull drama that seems almost calculated to win trophies from middlebrow tastemaking organizations. Surely that's a more feasible explanation for its making than the idea that Lloyd was actually compelled and moved by its story — a possibility which, if true, does not come through in a single scene. 

"Cavalcade" parades through its epochal narrative like a disinterested visitor walking at a uniform pace through a museum exhibit, covering each development in the Marryot family timeline perfunctorily, never lending depth or texture to any character. Even in the rare moments when the movie bothers to spring for emotion, it simply runs the sappiest sentimentality protocols and calls it a day.

To put it as clearly as possible, "Crash" won Best Picture because a large contingent of the Academy refused to give Best Picture to "Brokeback Mountain," a gay romance movie, in 2006. Not even Paul Haggis himself thinks "Crash" was the best film of 2005. But, if it were a worthy movie besmirched by a controversial win — in the manner of, say, "How Green Was My Valley," a John Ford masterpiece that won 20th Century Fox its first Best Picture Oscar, yet is doomed to be remembered as the movie that beat "Citizen Kane" — "Crash" wouldn't have the reputation it does. The reason it's routinely remembered as one of the most egregious Best Picture Oscar winners is that it is, well, an atrocious movie.

Much like "Cimarron" is a poor envoy for classic Westerns, "Crash" is handily the worst of the 2000s "hyperlink films" that could possibly have become the one to win Best Picture. The movie is all sizzle, all grandiloquent dramatics and intense gestures and would-be Big Scenes, without so much as an inkling of substance or profundity. To make matters worse, its exploration of racism, the theme that would supposedly unify all the interlocking storylines, is catastrophically shallow and regressive, substituting sensationalistic violence for cogency, and ultimately making no real point except "Everyone is a little bit racist, including people of color." If there's one thing for which racism is an actual unifying theme, it's undeserving Best Picture winners.

The first film to win the Best Picture Oscar, 1927's "Wings," was a silent film — and it was also the last silent film to win, until "The Artist" struck gold again in 2011 with its throwback homage. Just one year after "Wings," the American film industry was already so caught up in talkie fever that it even went ahead and gave Best Picture to a dreadful musical, strictly because it acted as a showreel for the new technology.

Another way to dissect the victory of "The Broadway Melody" would be to describe it as one of those cases of a movie that was so massively popular, such a box office juggernaut, that the Academy got swept up in a kind of herd effect and felt compelled to reward the money with trophies — a practice as old as the Oscars themselves, in case you were thinking it started in 2019 when "Bohemian Rhapsody" won four awards. Although talkies had debuted in 1927 with "The Jazz Singer," "The Broadway Melody" was their first big commercial expression, and going to see it was almost like a theme park attraction for movie audiences in 1929: Come watch actors sing and dance! Come watch the pictures talk!

The quality of the film itself was almost a non-factor, which might explain why, seen today, "The Broadway Melody" is little more than a paint-by-numbers showbiz musical with grating performances, unbearably repetitive numbers, and mostly forgettable songs.

What is interesting enough about the life of Broadway impresario Florenz Ziegfeld Jr. to engagingly fill a three-hour runtime? Not much, as it turns out, but that doesn't stop "The Great Ziegfeld" from trying.

In fairness, were the 1936 Robert Z. Leonard film shorter and more focused, it might actually have found a kernel of genuine psychological fascination in Ziegfeld's self-defeating, egomaniacal obsession with bloated spectacle. Instead, the movie gives in to that same bloated spectacle, deferentially recreating the "Ziegfeld Follies" and other Ziegfeld revues at enormous, stultifying length, and punctuating performance sequences with flashes of backstage drama that seem unaware of their potential for juicy fun.

At the heart of it all is William Powell in a performance that saddles him with repeating the same character beats over and over; his natural charisma as a performer is all but depleted by the third or fourth time Ziegfeld is floundering again and making a desperate bid for success again and miraculously reinventing himself again. Anticipating the blueprint of Oscar-ready biopics that seem satisfied with themselves for existing, content to relay biographical bullet points without bothering to find a compelling angle into their subjects or an artistic raison d'être, "The Great Ziegfeld" is a movie about the allure of aesthetic pleasure that offers little to no pleasure of its own.

And here we have the final boss of anodyne liberal movies about racism — and of '80s establishment taste. The '80s were one of the most fruitful decades ever for Hollywood cinema, but you wouldn't necessarily know it from the era's best-received films, which generally set out to counterweight the grittiness and risk-taking of the '70s by settling into a stable model of profitable prestige drama.

In 1989, "Driving Miss Daisy" rode that formula — respectable ambience, respectable structure, respectable cinematography, respectable storytelling, respectable dialogue, respectable values, not a smidge of discomfort or subversion — to glowing reviews and an easy Best Picture Oscar win, despite some dissent and controversy clouding its commercial success. It was only with hindsight that the egregiousness of said win became a widespread consensus, when the spell of '80s respectability cinema began to wear off, and the concept of a corny feel-good movie about a rich white widow (Jessica Tandy) learning to like and respect her saintlike Black driver (Morgan Freeman) stopped carrying built-in mainstream critical cachet.

By the turn of the 21st century, it became obvious that the movie's would-be lesson on interracial neighborliness was a big nothing compared to the actual, potent, lasting insights of Spike Lee's "Do the Right Thing," released the same year and not even nominated for Best Picture. By the time Lee lost Best Picture again to a movie about interracial passenger-chauffeur friendship in 2019 and rightfully stormed off in disgust, "Driving Miss Daisy" had become a national joke.

You might be noticing a pattern on this list: "Green Book" harbors little to no interest in the titular travel guide about Black-friendly establishments in the Jim Crow era; "Cavalcade" sorely lacks the rhythm and intensity of a cavalcade; "The Great Ziegfeld" does not make a particularly convincing argument for Ziegfeld's greatness. (To its credit, "Crash" really does feel like a messy road pile-up of a film.) And, if you can believe it, 1952's "The Greatest Show on Earth" was ... not that.

The only Best Picture winner directed by Cecil B. DeMille, the movie exemplifies the worst tendencies not only of the legendary American filmmaker, but of the Oscars themselves as an institution — and of Hollywood more broadly, for that matter. It's a clunking, self-important feat of megalomania that takes what should be a guaranteed fun subject — the circus — and completely saps it of wonder or joy, instead offering repeated testaments to its own massive budget and industrial scale of production, as if throwing dollar bills at viewers' faces and asking them to be awestruck. Some of the circus sequences are impressive enough, but the sense of danger and vulnerability and courage that makes the circus appealing is nowhere to be seen; in between set pieces, the movie plods impatiently and generically through its own story, utterly devoid of any real curiosity about the characters and the milieu it purports to reveal in up-close detail.

There's something endearing about "Around the World in 80 Days," a thoroughly awful movie that's nonetheless completely understandable and almost forgivable as a Best Picture Winner. As a time capsule of what made movie audiences tick in 1956, the Michael Anderson-directed film is kind of fascinating: Watching it, you can easily imagine viewers going "Ooh" and "Aah" while being introduced to world wonders for the first time in massive 70 mm cinematography, and there's even a certain quaint amusement to be had in watching the movie stack up cameos from huge stars, clearly angling for cheers, in the 1950s equivalent of the Avengers Assemble scene.

Sadly, as an actual viewing experience, "Around the World in 80 Days" is pretty miserable nowadays. Jules Verne's novel about an English gentleman (here played by David Niven) using his money and resources to circumvent the Earth as fast as possible has both an adventure and a wish fulfillment element to it, but Anderson's film keeps only the wish fulfillment, completely dispensing with any sense of urgency or tension or excitement in Phileas Fogg's quest. In their place, all that's offered is attraction upon attraction — dance sequences, bullfighting sequences, low-speed chase sequences, all the bang a 1956 theatergoer could get for their buck. Which would be fine — there's really nothing wrong with a good travelogue flick — if not for the fact that "Around the World in 80 Days" is three hours long, and gets to feel interminable.

Silver linings first: For what it's worth, the widescreen Metrocolor visual conception of "Gigi" is utterly splendorous. It's not the finest hour of Vincente Minnelli by any stretch, but he's still Minnelli, and his old-timey Paris is to die for. The songs, too, are mostly quite solid — with one very unfortunate exception — and help a lot of the movie's more arid stretches breeze by.

But alas, "Gigi" is pretty much all arid stretches — a film that approaches a thorny, somewhat unsavory subject with seemingly no real ideas about how it wants to tackle it, resulting in a mess both icky and dull. The movie adapts Sidonie-Gabrielle Colette's eponymous 1944 novella about a girl trained from a young age to be a courtesan. While Colette's writing was wry and sharply satirical, full of quietly corrosive insights about the commodification of relationships and of women's autonomy in Belle Époque Paris, Minnelli's "Gigi" is a straightforward romance, which casts the literally groomed relationship between the teenage Gigi (Leslie Caron) and the adult Gaston Lachaille (Louis Jordan) as cute and aspirational — and has a 70-year-old Maurice Chevalier sing a song called "Thank Heaven for Little Girls."

The oblivious skeeviness of that number is symptomatic of how there's no real weight or intelligence to any of the film's decisions — just a series of well-taken opportunities to make an expensive spectacle of Paris and its social scene. You'd be better off watching the lesser-known but much smarter 1949 adaptation directed by Jacqueline Audry.

Émile Zola was a great French writer who caused a seismic shift in literary history by writing sharply-observed novels about society's poor and disenfranchised. Late into his career, he took one of the bravest stands ever taken by an artist, jeopardizing his entire reputation to publicly denounce the antisemitic legal persecution of a Jewish French artillery officer, in what became known as the Dreyfus affair. William Dieterle's "The Life of Emile Zola" is a film that covers all that, but in the single most antithetical way possible to Zola's (Paul Muni) work: meekly and cautiously.

Somehow, the movie chronicles the injustice against Alfred Dreyfus (Joseph Schildkraut) without once mentioning the words "Jew" or "antisemitism" — a symptom of its 1937 production, a time when Nazism was on the rise and Hollywood was loath to ruffle feathers by antagonizing it. Without the actual specifics of the Dreyfus affair, all that's left for the movie is to dwell on mannerly prestige filmmaking tactics, pay vague lip service to Zola's ideals, and pat itself on the back; this is yet another Best Picture winner that makes you feel like you're watching the stuffy, pseudo-progressive Oscar bait biopic germinate in real time.

Every movie on this list is tedious and uninteresting in its own way. The Academy is much too fixated on staid notions of propriety to award the kind of trash that's fun to watch. However, "Tom Jones" is one of the absolute least watchable things a movie can be: A comedy that isn't funny at all. Directed by great English filmmaker Tony Richardson in maybe his least inspired work ever, the movie adapts Henry Fielding's 1749 picaresque novel, and, though it was released in 1963, "Tom Jones" really does feel like something people could only possibly have found hilarious in the 18th century.

That's really the movie's cardinal sin, much more than its bizarre staccato structure and near-absence of a proper plot — which would be fine, even stimulating traits for a better Best Picture winner to have. Unfortunately, "Tom Jones" replaces conventionally engaging storytelling with attempts at zany humor that at best don't land anymore, and at worst actively grate with their sheer misogyny and crassness. As much charm as Albert Finney tries to impart to his womanizing chivalric hero, he is just resoundingly annoying as scripted; it never really gets fun to watch him swagger and flirt his way through 18th-century England. The best explanation for "Tom Jones'" Best Picture win is that it may have sparked a "Shrek"-esque morbid catharsis by skewering Oscar-friendly pompous historical dramas. But there's not much use in a parody that's as boring as its target.