8 Worst Movies That Won Multiple Oscars

Image via Netflix Published Jul 29, 2026, 7:51 AM EDT Diego Pineda has been a devout storyteller his whole life. He has self-published a fantasy novel and a book of short stories, and is actively working on publishing his second novel. A lifelong fan of watching movies and talking about them endlessly, he writes reviews and analyses on his Instagram page dedicated to cinema, and occasionally on his blog. His favorite filmmakers are Andrei Tarkovsky and Charlie Chaplin. He loves modern Mexican cinema and thinks it's tragically underappreciated. Other interests of Diego's include reading, gaming, roller coasters, writing reviews on his Letterboxd account (username: DPP_reviews), and going down rabbit holes of whatever topic he's interested in at any given point. Sign in to your Collider account 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) Image via TWC 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) Image via Warner Bros. Pictures 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) Image via 20th Century Studios 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) Image via 20th Century Studios 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. Collider Exclusive · Oscar Best Picture Quiz Which Oscar Best PictureIs Your Perfect Movie? Parasite · Everything Everywhere · Oppenheimer · Birdman · No Country Five Oscar Best Picture winners. Five completely different visions of what cinema can be — and what it can do to you. One of them is the film that was made for the way your mind works. Ten questions will figure out which one. 🪜Parasite 🌀Everything Everywhere ☢️Oppenheimer 🐦Birdman 🪙No Country for Old Men FIND YOUR FILM → 01 What kind of film experience do you actually want? The best movies don't just entertain — they leave something behind. ASomething that pulls the rug out — that makes me think I'm watching one kind of film and then reveals I'm watching another entirely. BSomething overwhelming — funny, sad, absurd, and genuinely moving, all at once. CSomething grand and weighty — a film that makes me feel the full scale of what I'm watching. DSomething formally daring — a film that pushes what cinema can even do. ESomething lean and relentless — pure tension with no wasted frame. NEXT QUESTION → 02 Which idea grabs you most in a film? Great films are driven by a central obsession. What's yours? AClass, inequality, and what people are willing to do when desperation meets opportunity. BIdentity, family, and the chaos of trying to hold your life together when everything is falling apart. CGenius, moral responsibility, and the catastrophic weight of a decision you can never take back. DEgo, legacy, and the terror of becoming irrelevant while you're still alive to watch it happen. EEvil, chance, and whether moral order actually exists or if we just tell ourselves it does. NEXT QUESTION → 03 How do you like your story told? Form is content. The way a story is shaped changes what it means. AGenre-twisting — I want it to start in one lane and migrate into something completely different. BMaximalist and genre-blending — comedy, action, drama, sci-fi, all in one ride. CEpic and non-linear — cutting between timelines, building a mosaic of cause and consequence. DA single unbroken flow — I want to feel like I'm living it in real time, no cuts to safety. ESpare and precise — every scene doing exactly what it needs to do and nothing more. NEXT QUESTION → 04 What makes a truly great antagonist? The opposition defines the protagonist. What kind of opposition fascinates you? AA system — invisible, structural, and almost impossible to fight because it has no single face. BThe self — the ways we sabotage, abandon, and fail the people we love most. CHistory — the unstoppable momentum of events that no single person can stop or redirect. DThe industry — the machinery of culture that chews up talent and spits out irrelevance. EPure, implacable evil — a force so certain of itself it becomes almost philosophical. NEXT QUESTION → 05 What do you want from a film's ending? The final note is the one that lingers. What do you want it to sound like? AShock and inevitability — a conclusion that recontextualises everything that came before it. BEarned emotion — I want to cry, laugh, and feel genuinely hopeful, even if the world is a mess. CDevastation and grandeur — an ending that makes me sit in silence for a few minutes after. DAmbiguity — something that leaves enough open that I'm still thinking about it days later. EBleakness — an honest refusal to pretend the world is tidier than it actually is. NEXT QUESTION → 06 Which setting pulls you in most? Where a film takes place shapes everything — mood, stakes, what's even possible. AA gleaming modern city with a hidden underside — beauty masking rot, wealth masking desperation. BA collapsing suburban life that opens onto something infinite — the multiverse of a single ordinary person. CThe corridors of power and science at a world-historical turning point — where decisions echo for decades. DThe grimy, alive chaos of New York and Hollywood — fame as both destination and trap. EVast, indifferent landscape — desert and highway where violence arrives without warning or reason. NEXT QUESTION → 07 What cinematic craft impresses you most? Every great film has a signature — a technical or artistic element that makes it unmistakable. AProduction design and mise-en-scène — every frame composed to carry meaning beneath the surface. BEditing and tonal control — the ability to move between registers without losing the audience. CScore and sound design — music that becomes inseparable from the dread and awe of what you're watching. DCinematography as performance — the camera not recording events but participating in them. ESilence and restraint — what's left unsaid and unshown doing more work than any dialogue could. NEXT QUESTION → 08 What kind of main character do you root for? The protagonist is the lens. Who you choose to follow says something about you. ASomeone smart and resourceful who makes increasingly dangerous decisions under pressure. BSomeone overwhelmed and ordinary who turns out to be capable of something extraordinary. CA brilliant, tortured figure whose gifts and flaws are inseparable from each other. DA self-destructive artist whose ego is both their superpower and their undoing. EA quiet, principled person trying to make sense of a world that has stopped making sense. NEXT QUESTION → 09 How do you feel about a film that takes its time? Pace is a choice. Some films sprint; others let tension accumulate slowly, deliberately. AI love a slow build when I know the payoff is going to be seismic — patience for a devastating reveal. BGive me relentless momentum — I want to feel breathless and emotionally spent by the end. CEpic runtime doesn't scare me — if the material demands three hours, give me three hours. DI want it to feel propulsive even when nothing is technically happening — restless energy throughout. EDeliberate and unhurried — I want dread to accumulate in the spaces between the action. NEXT QUESTION → 10 What do you want to feel walking out of the cinema? The best films leave a mark. What kind of mark do you want? AUnsettled — like I've just seen something I can't fully explain but can't stop thinking about. BMoved and energised — like the film reminded me what actually matters and gave me something to hold onto. CHumbled — like I've been in the presence of something genuinely important and overwhelming. DExhilarated — like I've just seen cinema doing something it's never quite done before. EHaunted — like a cold, quiet dread that stays with me for days. REVEAL MY FILM → The Academy Has Decided Your Perfect Film Is…Your answers have pointed to one Oscar Best Picture winner above all others. This is the film that was made for the way your mind works. ParasiteYou are drawn to films that operate on multiple levels simultaneously — that begin in one genre and quietly, brilliantly migrate into another. Bong Joon-ho's Parasite is a film about class, desire, and the architecture of inequality that manages to be darkly funny, deeply suspenseful, and genuinely shocking across a single extraordinary running time. Your instinct is for cinema that hides its true intentions until the moment it's ready to reveal them. Parasite is exactly that — a film that rewards close attention and punishes assumptions, right up to its devastating final image. Everything Everywhere All at OnceYou want it all — and this film gives you all of it. The Daniels' Everything Everywhere All at Once is one of the most maximalist films ever made: action comedy, multiverse sci-fi, family drama, existential crisis, and a genuinely earned emotional core that sneaks up on you amid the chaos. You are someone who responds to ambition, who doesn't want cinema to choose between being entertaining and being meaningful. This film refuses that choice entirely. It is overwhelming by design, and its overwhelming nature is precisely the point — because the feeling of being crushed by infinite possibility is exactly what it's about. OppenheimerYou are drawn to cinema on a grand scale — films that understand history not as a backdrop but as a force, and that place their characters inside that force and watch what happens. Christopher Nolan's Oppenheimer is a film about the terrifying gap between what we can do and what we should do, told with the full weight of one of the most consequential moments in human history behind it. You want your films to feel important without feeling self-important — to earn their ambition through sheer craft and the gravity of their subject. Oppenheimer does exactly that. It is enormous, complicated, and refuses easy comfort. BirdmanYou are drawn to films that foreground their own construction — that make the how of the filmmaking part of the what it's about. Alejandro González Iñárritu's Birdman, shot to appear as a single continuous take, is cinema examining itself through the cracked mirror of a fading actor's ego. You respond to formal daring, to the feeling that a film is doing something that probably shouldn't be possible. Michael Keaton's performance and Emmanuel Lubezki's restless camera create something genuinely unlike anything else — a film that is simultaneously about creativity, relevance, self-destruction, and the impossibility of ever truly knowing if your work means anything at all. No Country for Old MenYou are drawn to cinema that trusts silence, that refuses to explain itself, and that treats dread as a form of meaning. The Coen Brothers' No Country for Old Men is a film about the arrival of a new kind of evil — implacable, arbitrary, and utterly indifferent to the moral frameworks we use to make sense of the world. It is one of the most formally controlled films ever made, and its controlled restraint is what makes it so terrifying. You want your films to haunt you, not comfort you. You are not interested in resolution if resolution would be dishonest. No Country for Old Men is honest in a way that most cinema never dares to be. ↻ RETAKE THE QUIZ 2 'Cimarron' (1931) Image via RKO Radio Pictures 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) Image via Netflix 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 November 13, 2024 Runtime 130 Minutes Cast Karla Sofía Gascón Emilia / Manitas