The 21 Most Unique Best Picture Winners in Oscars History
Written by Andreas Babiolakis
Ever heard the term “Oscar Bait”? It is applied to films that are built solely to win awards (particularly ones by the Academy). We are all used to seeing dramas, epics, war films, and other Academy Award mainstays win many trophies, including the coveted top prize: Best Picture. By the time I write this article, there have been ninety five Best Picture winners (well, ninety six: more on that soon). It is safe to say that roughly twenty percent of all Best Picture winners actually feel a little different from what you would expect. Which films felt refreshing when they won? Which motion pictures stand out amongst the others because they are unusual, different, or just unexpected? Here are the twenty most unique Best Picture winners in Oscars History.
Note: These selections don’t necessarily mean that these films are better than the other Best Picture winners ever. Many masterpieces are left off of this list because they feel like they fit in to the Oscars’ history of awards rather nicely.
Sunrise: A Song of Two Humans
Two technicalities here. First: Sunrise: A Song of Two Humans is actually one of the first Best Picture winners ever, sharing the award with Wings. The very first Academy Awards had two separate awards for Best Picture: Unique and Artistic Picture (Sunrise), and Outstanding Picture (Wings). While the latter is what is actually considered Best Picture now, how could I turn down the magnificent, aesthetic whirlwind that is Sunrise? This is a groundbreaking silent film that used minimal instances of recorded sound to create atmosphere within this stylized, somewhat-expressionist world. The end result is a fever dream between estranged lovers that reunite and find paradise in everyday life. It’s kind of fitting that the sole winner of the Unique and Artistic Picture is a standout feature in Academy history; not that there’s anything wrong with Wings (it’s a terrific film), but the Academy would lean towards technically strong epics and straightforward dramas from here on out.
Grand Hotel
Grand Hotel isn’t a strange film by any means, but you’ll be hard pressed to find a Best Picture winner like it. This is a series of storylines of different kindred spirits that all take place within the titular location; the idea is that you never know what will take place each night within this popular hotel. As you wander the halls and climb floors to revisit each and every story, the main central theme is that life is unpredictable. You invade the privacy of travellers behind close doors, and I think it’s this level of candidness that spoke to the Academy. One other kicker that makes Grand Hotel truly unique is that it won Best Picture and wasn’t even nominated in any other category. Make sense of that, if you will.
Cavalcade
Not every film on this list will be good. Cavalcade is actually quite rough, but it’s the interesting premise that places it here. We follow the Marryot family through a number of historical events at the turn of the twentieth century, including the death of Queen Victoria, both World War I and the Second Boer War, and even the sinking of the Titanic (so it is the first Best Picture winner about that subject matter). While these different vignettes aren’t explored well enough, Cavalcade is still a tapestry of history that expresses the magnitude of circumstance and the agility of time, as we soar through decades of one family’s existence (we even cut through different generations). Not a good film but a unique idea.
Rebecca
The next film to feel out of place within the history of the Best Picture award is Alfred Hitchcock’s frigid Rebecca (sadly, this is also unique feeling because the Oscars barely ever showed Hitchcock and his films much love otherwise). This film likely had a bit of help with producer David O. Selznick’s name attached to it (he produced the previous year’s big winner, Gone With the Wind), but that doesn’t take away from how singular this gothic, psychological drama is. Featuring a protagonist without a name and the mysterious spirit that hypnotizes her (Maxim de Winter), Rebecca is a spooky downward spiral of ghastly proportions that borders on the edge of being a horror film at times. Oscar baited films are romanticized and lush. Rebecca couldn’t be any further from this; it’s a cynical depiction of love from a cast of mannequins that cast dread — not chemistry — amongst each other. It’s ironically delightful in this way.
The Lost Weekend
As the criteria for being a Best Picture winner was being molded, Billy Wilder’s dismal The Lost Weekend became the first film to win both the Palme d’Or (then known as the Grand Prix) and the Academy Award’s biggest prize. In this psychological noir film, all that happens is that we are cooped up with an alcoholic writer that battles his addiction on the titular weekend (which gets in the way of a major assignment). We follow him to the depths of hell, including an unforgettable night of hallucination caused by withdrawal symptoms. The Lost Weekend isn’t all terrifying, but I feel like Wilder would have gone the distance if the film didn’t have to abide by the Hays Code. A Wilder film would win Best Picture again a little more than ten years later: the magnificent The Apartment.
Tom Jones
Again, not every film on this list is great. Just because a film doesn’t feel like your typical Best Picture winner, that doesn’t mean that it’s actually strong. Case in point: Tom Jones. This strange period piece feature is an exercise conducted by director Tony Richardson: to see how much a conventional film can be broken while still being recognizably orthodox. The titular playboy, played by Albert Finney, feels like a then-modern-day participant of the Swinging London years (much like the films Alfie, The Knack… and How to Get It, and Kaleidoscope) transported to the eighteenth century. That’s not the only sense of modernity here: Richardson explores the breaking of fourth walls, nearly-arthouse aesthetics, and tons of self-aware storytelling. These choices don’t always work, but they apparently left an impression on the Academy back in 1963/1964.
Midnight Cowboy
The first X-rated film to win Best Picture, Midnight Cowboy is likely not what the attendees of the very first Academy Awards envisioned for the future of the ceremony. A Texan vagabond heads to New York City to become a gigolo; already, you can see why this feels like quite a different Best Picture winner. He arrives in the city that never sleeps, and it isn’t all bells and whistles like he imagined. As he and his partner in crime struggle to survive, this blend of counterculture cinema and the death of the American dream is anything but hopeful. This was a major turning point: when New Hollywood cinema was crashing down on the ways of old.
The French Connection
After Midnight Cowboy, the sky was the limit for more antithetical features. Enter The French Connection: William Friedkin’s combination of New Hollywood and the French New Wave movement. We’ve seen the Academy award gritty films since (The Deer Hunter and The Departed come to mind), but The French Connection is so unorthodox for its time that it still feels more atypical for the Oscars to honour. With purposefully choppy editing, a lack of polish, and one of cinema’s most concerning antiheroes in detective Popeye Doyle, Friedkin’s film is experimental enough to leave an impact, whether you’re the Academy voters of the early 70s or a modern day viewer that is still blown away by how daring this film is.
Annie Hall
Somewhat similar to Tom Jones (whilst being significantly better), Annie Hall is an extremely self aware film that breaks the fourth wall more times (and even goes much further with its meta commentary and design). It sounds silly, but another thing that makes Annie Hall feel unique in Academy history is that it is actually a straight up comedy. Comedies don’t typically get much Academy love (if you don’t believe me, I encourage you to flip through every Oscar winner ever and do the math of how often straight up comedies — not dramedies, historical comedies, musicals, et cetera — win), especially not for Best Picture. It definitely has happened before, but more so during the early days of the Academy Awards (like It Happened One Night and You Can’t Take It With You), but Annie Hall winning in the seventies (when the Oscars had its uppity identity) still stands out.
The Last Emperor
Released during one of the safer decades of the Academy Awards is Bernardo Bertolucci’s The Last Emperor. This reads like another biopic on paper, but Bertolucci’s affinity for arthouse cinema can be felt here (even if the film is still considerably straightforward by his standards, it still feels quite out there for the Oscars). Focusing on the final years of the Forbidden City (and Puyi’s reign as the titular last emperor there), as well as the political shifts in China and Japan, Bertolucci’s masterpiece may speak enough of the Academy’s language to be noticed (a large, ambitious, historical epic). However, there’s enough of his aesthetic, creative thumbprint to make The Last Emperor such a refreshing win; I consider it one of the more underrated, under-loved Best Picture winners to this day.
The Silence of the Lambs
Jonathan Demme’s psychological horror, The Silence of the Lambs, is forever a part of Oscars lore. Not only did a genre film (specifically a horror film, which the Academy hates far more than comedies) win Best Picture, it also is one of the only films to win all five of the top prizes: Best Picture, Best Director, Best Actor, Best Actress, and either of the screenplay awards (It Happened One Night and One Flew Over the Cuckoo’s Nest being the other two films). An FBI student, Clarice Starling, is on the hunt for serial killer Buffalo Bill and needs imprisoned cannibal Hannibal Lecter’s help to stop the murders. Terrifying, gory, and quite unhinged for its time, The Silence of the Lambs is anything but a safe film. It almost feels impossible that this won Best Picture, but maybe the Academy can’t say no to one of the greatest thrillers of all time.
American Beauty
We’ve seen dramas win Best Picture before, but not something quite like American Beauty: the existential antithesis to the American Dream. By the tail end of the twentieth century, it felt like the promises of success in the United States were all but a lie. Sam Mendes and Alan Ball have this answer to all of the patriotism that was blindly followed after the decline of the New Hollywood movement: a film that questions everything and insists that there isn’t a definitive answer to how one should live their life. It’s cooky, awkward, strange, and full of self loathing, but American Beauty is a brilliant deconstruction of conventions.
The Lord of the Rings: The Return of the King
On one hand, The Return of the King is not unlike most of the war epics that have won Best Picture if you really think about it. People have accepted that this third entry of Peter Jackson’s The Lord of the Rings trilogy is an Oscars titan (it is tied with Ben-Hur and Titanic with the most wins in Academy Awards history with eleven trophies). Take a step back and see what we have here: we have a fantasy film (only one other has won Best Picture: more on that later), and a second sequel in a franchise (the only other sequel to win is The Godfather Part II). This won Best Picture. It actually swept the awards. We’ve accepted this as if this is normal. It’s worth noticing that this is actually extraordinary.
No Country for Old Men
A few westerns won Best Picture before (the terrible Cimarron, the quite-good Dances with Wolves, and the perfect revisionist film Unforgiven), but No Country for Old Men — if you can even consider it a western (I do) — is on its own. Quite possibly the bleakest film to ever win Best Picture, this nihilistic game of cat-and-mouse never holds your hand. Not once. As Anton Chigurh takes on the symbolic role as death itself traversing across the southern states and northern Mexico, we see life affected and/or terminated again and again. Death comes for everyone. Even the film itself cuts off abruptly, which bothered many viewers when it was released; I find a bit of comfort in this brave decision. No Country for Old Men is anything but Oscar bait.
The Artist
Yes. Technically one (or two, if you consider Sunrise a winner) silent film previously won Best Picture, but The Artist was made when the invention of talkies was over eighty years old and almost no one was making silent pictures. Remember when this film came out and some people were actually worried that this would be a gimmick that kept being done? That was stupid. Anyway, The Artist is a splendid love letter to the cinema of yesteryear: a turning point where many jobs were cost in order to usher in the innovation of sound in film. The Artist is creative with its homages and approaches, and it remains a touching experiment. If it was somewhat overrated when it first came out, I’d call it under-loved now: it still holds up really well, folks.
Birdman or (The Unexpected Virtue of Ignorance)
Not only is Birdman quite dark with its comedy (which is always welcome), its depictions of existentialism are so clever, as the stage meets cinema in one homogenous experience. An illusion of one single shot makes us feel like we are watching a stage adaptation, yet the inhibitions of blockbuster cinema keep colliding with traditionalism; this tug-of-war is the heart of Birdman, and surrounding it are discussions on art versus criticism, objectivity versus subjectivity, and legacy versus identity. When Birdman won, it almost felt miraculous: something this different, creatively bitter, and idiosyncratic could win the Academy over.
Moonlight
If The Last Emperor was at least slightly arthouse, then Barry Jenkins’ Moonlight is the most arthouse Best Picture winner to date. This film is much more akin to the films of Wong Kar-wai (of whom is never really honoured by the Academy, sadly) than your typical Oscars fair. As we zip through three different chapters of Chiron’s life (and experience Black queerness in Miami), we see a lone soul who is forced to change his identity in order to survive in a rough neighbourhood. Courageous, aesthetically brilliant, authentically moving, and enlightening, Moonlight continues to feel like one of the most refreshing selections for Best Picture (sadly, as we all know, this punctuation point was robbed by a major snafu).
The Shape of Water
Guillermo del Toro’s Cold War fantasy romantic drama, The Shape of Water, was a tough sell for many people that reserve to watch films until after they win Oscars. They didn’t want to watch the film where a woman makes out with a fish monster, but they would be missing the point entirely. This beautiful fairy tale is so magical, loving, and profound, as its grace is as strong as its gore and imagination. Del Toro is the master of making adults feel like children again, as they gaze upon whimsical journeys; of course, these dreams get destroyed by the director’s nightmarish cuts to reality, but we’re more blessed by his affinity of finding warmth in the most unusual places and beings. I don’t care what anyone says: The Shape of Water is sublime.
Parasite
Let’s get the obvious out of the way: Parasite is the very first Best Picture winner to not be in English (I’d similarly include CODA here for its major usage of American Sign Language, but I do think the story is much more straightforward and stripped down than most of the other films included here). Bong Joon-ho’s genre bender (it’s part black comedy, mystery, thriller, and even familial drama) is so atypical of what we’ve seen do well over the course of the Oscars, but I’ll never forget how great it felt when this won. It’s nice to see the actual best film of a year win Best Picture, a film from another country and another language winning opens the door of possibility for many, and such a creative premise being honoured was a nice change of pace (I think many of us are exhausted of the same-old formulas and themes winning time and time again).
Nomadland
Five films from the previous decade are included on this list, which to me means that the Academy Awards are branching out a bit in its old age. The 2020s are off to a similar start with the docudrama Nomadland. Chloé Zhao’s magnum opus follows a recently laid off woman that travels across America in her van. The many people Frances McDormand’s character meets are real nomads that represent themselves. Zhao allows the natural lighting to also paint a story of realism, as we find breathtaking sights amongst the realities of hardship. It still feels unusual that the Academy willingly went for a film this minimalist, spiritual, and raw (especially when similar directors like Terrence Malick have barely been given a fair chance by the very same group).
Everything Everywhere All at Once
We arrive with our latest winner (as I write this): Everything Everywhere All at Once. I was inspired to write this list because of this film; it flat out has to be the most unique film to ever win Best Picture. Multiverse story aside, this is another genre bender that somehow pulls off all of its separate missions (it is a hilarious comedy, a heartbreaking drama, an even heavier romance, a kickass action film, a sci-fi adventure, and even slightly terrifying at times). Besides, what other Best Picture winner has someone being bludgeoned to death by dildos, self-inflicted paper cuts, trophies going where they shouldn’t be going, and a meditative moment where we are all just rocks existing without purpose? I haven’t even scratched the surface as to what you’ll find in this extraordinarily bonkers film by the Daniels. Not only did this film win the top prize, it is the most accoladed Best Picture winner since Slumdog Millionaire well over ten years before (Everything Everywhere is actually the most accoladed film of all time, with over one hundred and sixty wins across all ceremonies). Despite its absurdities, this film just speaks to almost everyone.
Andreas Babiolakis has a Masters degree in Film and Photography Preservation and Collections Management from Toronto Metropolitan University, as well as a Bachelors degree in Cinema Studies from York University. His favourite times of year are the Criterion Collection flash sales and the annual Toronto International Film Festival.