As much as the people who handle the marketing for the Academy Awards would like to present the honor as an artistic one, its not entirely true. Arguably, that’s what their Governors Awards are for, but the true rewards of receiving an Oscar come in the form of funding. It’s essentially a great PR boost and that shouldn’t be looked down on or considered any less important than any honors in artistic accomplishment and technical skill. Martin Scorsese secured money for towering, radical masterworks like The Wolf of Wall Street and Silence because of the Oscar love for one of his least ambitious works, The Departed. The late Jonathan Demme’s wins for his own masterpieces, Philadelphia and The Silence of the Lambs, allowed him to continue a career defined by audacity in form and subject matter. The same could be said of Spike Lee, Steven Soderbergh, Richard Linklater, and a number of other filmmakers that have defined the best of American filmmaking over the last few decades.

Image via A24

And yet, for those who have been and likely always will be drunk on the movies, it’s an impossible task to not feel that the Oscars should be a reflection of the state of cinema in America, reserved for movies that are fearless, unique, and overflowing with political and philosophical ideas. In rare cases, such as with The Best Years of Our Lives or The Hurt Locker, the distance between the artistic merits of the year’s Best Picture winner and its polished reflection of what Academy members want to be seen as caring most about is not that far. To bolster a movie about the startling psychological damage and fatalistic pull of war at a time when the public is exhausted with the Iraq War makes the governing body look smart and serious while also celebrating an artist as thoughtful and excessively talented as Kathryn Bigelow. Most of the time, however, the divide is much greater.

To separate the great from the good and the good from the bad, I have ranked every single Oscar winner for Best Picture and plan to update it on an annual basis. If you just can’t stand the numbers here, sound off in the comments.

91) 'Driving Miss Daisy' (1989)


What an absolutely wretched undertaking. Though it’s not uncommon to waste the talents of Morgan Freeman, this extended fit of soft-boiled racism deserves a special amount of derision for being so insufferable to gaze upon, conveying the unique feeling of being smothered by lamp doilies. The script is a forced game-show-host grin in the face of America’s tradition of enslaving black Americans, and even when that’s not readily apparent, the family drama stuff with Jessica Tandy’s titular crank and her son (poor Dan Aykroyd) is also about as exhilarating as the annual San Bernardino Ankle Sock Convention. Make it go away!

What Should Have Won: My Left Foot

90) 'Crash' (2005)


A photo-fucking-finish with the previous entry, but this one has the better cast being drowned in well-meaning sap. Paul Haggis at once energized and deflated his career with this astonishingly wrong-headed attempt to surmise and solve modern-day racism during one week of grim, ugly nonsense in Los Angeles. Don Cheadle, Matt Dillon, Thandie Newton, Terrence Howard, Sandra Bullock, Chris “Ludacris” Bridges, and Michael Peña, just to start, try valiantly to give this thing some lifeblood but it all comes off like politically agreeable hokum, which makes its ambitions all the more embarrassing. It’s a work of staggering condescension from beginning to end.

What Should Have Won: Capote

89) 'Green Book' (2018)


Not very long into Green Book, Viggo Mortensen’s Tony “Lip” Vallelonga, a bouncer, driver, and part-time bruiser for the New York mafia, disposes of two glasses because they were used by black service men working in his home. One might argue that Tony’s apparent deep-seated racism in this moment is meant to be performative – he does so in the company of his friends who are all exactly like him – but director and co-writer Peter Farrelly certainly doesn’t go to any trouble to highlight that, and that’s not how I read it when I saw the movie last November. What you see is a white man who is offended by the idea of drinking out of the same glasses as black men, even if they were to be washed.

Racism isn’t portrayed as particularly scary or malevolent in Farrelly’s movie, at least not to the point where you might remember that white supremacists are currently enjoying a rejuvenated public acceptance both in America and Europe. In fact, it’s not all that long after Tony is hired by Dr. Don Shirley (Mahershala Ali), the pioneering jazz pianist and composer, to drive him from gig to gig on a 1962 tour of the American South that any sense of Tony being anything but dumb, crude, and a little insensitive is eliminated, as if he’d never put those glasses in the garbage at all. Amongst the innumerable failures of Green Book is its refusal to consider the work of change and empathizing. Tony doesn’t really have to do any soul-searching to become an ally, and he doesn’t have to struggle with any familial or social constructs that helped build up such intolerance. Eventually, he just kind of gets it.

The emptiness and regressive nature of this well-meaning gesture toward unity may not smack you in the face immediately, and that’s largely thanks to Farrelly and his technical team. Visually, Green Book is his most accomplished film to date. The pacing is steady and breezy; the compositions are mostly appealing but never exhilarating; the wardrobe, production design, and set design are all stellar; and the cast is uniformly excellent. Farrelly has attained the false respectability in his films that he’s been chasing ever since the early aughts and has ensured himself a few more high-paying gigs in the bargain. In doing so, he’s also ensured a multi-million-dollar career for an Islamaphobe, namely co-writer and producer Nick Vallelonga, Tony’s real-life son. For whatever he meant it to be, Farrelly’s movie is a relic so desperate for relevancy and popularity that it avoids confronting the issues at the very core of its central relationship. In hindsight, there’s really no other movie that could have won.

What Should Have Won: BlacKkKlansman

88) 'Rain Man' (1988)


An asshole, played by Tom Cruise, belittles and attempts to make a quick fortune off of his long-lost autistic brother for two hours in this miserable ordeal. Give credit to Dustin Hoffman for devoting himself to a deeply wrong-headed character and Barry Levinson’s direction is both breezy and efficient but even for someone who isn’t fond of extolling popular morality, it’s hard to see any good in this. Other than reasserting well-treaded family values and reminding people to be kind to those with mental disorders, Rain Man brandishes little in the way of thought or political curiosity. That it’s also a tremendous bore does not help matters.

What Should Have Won: Dangerous Liaisons

87) 'Shakespeare in Love' (1998)


On first glance, this one’s fine: excellent technical work from the set design down to the wardrobe, exuberant performers, and a playful-enough story. Once you start thinking about the film, however, things are a bit less agreeable. Gwyneth Paltrow is not very good but is also not given much to work with here, and the script’s perspective on Shakespeare is borderline offensive. He’s a total cad, a drunk, and a horrid friend who steals freely from Christopher Marlow (Rupert Everett) and is then edited down by performers and producers, who were instrumental in his genius. As the film has it, Shakespeare is no different from Kramer in his absent-minded good luck, and that makes the more self-serious stretches of this bloated, insufferably cute romantic comedy all the more impossible to care about. A hearty nod for scene-stealers Geoffrey Rush, Ben Affleck, and, yes, Dame Judi Dench, but the film remains predictable, lazily paced, and unfunny in the extreme, edited into a visual mush for costume drama fans.

What Should Have Won: The Thin Red Line

86) 'The Artist' (2011)


The ultimate legitimization of nostalgia and gimmickry over invention – remember, this won over Terrence Malick’s The Tree of Life and Hugo, a much better movie about the imaginative spirit and creatively technical minds that made silent film such a wonder. This broad-as-fuck challenge to make a silent movie adds exactly nothing to the film’s base-level charms, as it seems even more interested in venerating the power of classical Hollywood storytelling. As a reflection of the industry it professes to love, it’s pretty flat and shows none of the obsessive nuance and feeling of experience that powers the best movies about making movies. Director Michel Hazanavicius is more than competent in his visual excursions but rarely exhilarating or even particularly charming. Rather than searching for the luxurious sense of textures, the thick, lavish shadows of the bygone era of cinema, The Artist feels like a movie that was given its nostalgic heft in post-production, the true art of the silent era boiled down to a few clicks of the mouse.

What Should Have Won: The Tree of Life

85) 'Slumdog Millionaire' (2008)


You’ll have to pardon the cynic in me on this one but: What’s with all the incessant joy in this movie? Danny Boyle’s attempt to give the world a sense of Indian culture in the story of a poor young boy who turns into a bright romantic (Dev Patel) also allows the Trainspotting director to take the Bollywood format out for a test spin. This is one of those Triumph of the Cute situations, where an incredibly important subject – the fate of the poor and abandoned in post-colonial India – is mutated into an occasionally winning but largely saccharine and tedious romantic comedy. The movie is a greatest hits of Boyle’s worst visual tendencies and it zaps the film of any perceived interest in the land of India and the tight corridors of its neighborhoods and cities. The inclusion of the game show as a framing device underlines the film’s playfulness, which feels at odds with its increasingly insincere interest in the history and complicated politics of the country.

What Should Have Won: The Curious Case of Benjamin Button

84) 'Out of Africa' (1985)


On one hand, it’s a biopic about famed female humanitarian and writer Karen Blixen, played with quiet but potent and often physical energy by Meryl Streep, who begins an intimate extramarital affair with an enigmatic hunk (Robert Redford) in Kenya. On the other hand, it’s directed by the late Sydney Pollack, whose movies regularly boast narrative efficiency and bucolic settings but little in the way of personal reflection or any sense of a vast, complex inner world within his characters. The story is interesting, up to a point, but the timidity of the overall production catches none of the innumerable fascinating things about Streep’s character or the men and animals she must handle with care.

What Should Have Won: Prizzi’s Honor

83) 'Kramer vs. Kramer' (1979)


A softball, borderline misogynistic depiction of divorce that spends half the time patting itself on the back. An ambitious, talented, and well-off professional (Dustin Hoffman) becomes a single parent when his wife (Meryl Streep) runs off to explore herself, an act that is only seen from the husband’s perspective and is portrayed almost exclusively as selfish. That’s certainly part of the mix of feelings, but Kramer vs. Kramer is not, in any way, interested in what the mother’s exploration is or where it comes from. Instead, it acts to lionize the single father, especially one with a creative streak. There’s also a severe lack of intimacy: the scenes between father and son feel more suited to a credit card commercial than an empathetic, experienced depiction of being a single parent with a full-time job. At this point, the movie feels like a propaganda video from the left wing of the Men’s Rights movement.

What Should Have Won: Apocalypse Now or All That Jazz

82) 'A Man for All Seasons' (1966)


The quasi-lead performance from Robert Shaw is the sweet, syrupy plum amongst a lump of bland porridge here. The Jaws actor’s take on King Henry VIII is thoughtful, aggressive, and rousingly intricate in the rhythms of its delivery, and he is backed with considerable force by Paul Scofield as Thomas More, Orson Welles, Wendy Hiller, John Hurt, and Susannah York. They all take great glee in diggint into Robert Bolt’s screenplay, which he adapted from his own beloved play of the same title. The players and the words are the beating heart inside a calcified cadaver of a movie, which fails to muster even a single image that conveys any kind of personality or ideas beyond the text. It’s a filmed play essentially, something that director Fred Zinnemann would become known for and the Oscars would continuously reward for not particularly good reasons. For all its basic entertainment value, it shows a severe deficit of visual invention.

What Should Have Won: Who’s Afraid of Virginia Woolf?

81) 'Argo' (2012)


The premiere example of Hollywood’s vacant self-interest. Rather than show anything beyond a passing interest in Iran’s modern chaotic state or, say, America’s hand in developing said bedlam, writer-director Ben Affleck focuses almost exclusively on the handful of American hostages that were in danger during the uprising and the fraudulent film crew that saved them. The movie is primarily a celebration of Hollywood’s clout and the importance of the medium that they have popularized, as it is ultimately those things that distract or impress the Iranian government and people enough to hatch their escape plan. Affleck’s gift for visual tension is deployed far more efficiently in The Town and Gone Baby Gone, and neither of those films felt so profoundly self-important yet pompously careless as Argo does by the end of its excessive runtime.

What Should Have Won: Zero Dark Thirty

80) 'A Beautiful Mind' (2001)


Not unlike future nominee The Imitation Game, Ron Howard’s take on the life of cryptography pioneer John Nash (Russell Crowe in fine form) is noticeably hindered by its omissions in personal history. Screenwriter Akiva Goldsman has a long, storied career of writing sentimental, nonsensical gibberish for untold amounts of money and here, his attempts to restrain the more not-so-family-friendly elements of Nash’s life – repressed homosexuality, just to start – stick out like a broken algorithm. Howard is, as always, capable and efficient in his plain, classical stylization and the cast, including Ed Harris, Jennifer Connelly, and Paul Bettany, is uniformly compelling but the very blueprints of the movies are cripplingly faulty. Not only is it a piss-poor depiction of mental illness and treatment, it’s an expression of competency in the face of inarguable, imposing genius of a very rare sort.

What Should Have Won: Gosford Park

79) 'Chicago' (2002)


This is around the part of the list where we get into straight mediocrities, which make up the majority of this list. Indeed, most of the movies that have won best picture are not out-and-out bad but rather weak tea. Such is certainly the case with Hollywood’s long-gestating adaptation of Chicago, the Broadway smash centered around the trial of saucy husband-killer Roxie Hart, played by Renee Zellwegger. Richard Gere is having a ball as Billy Flynn, her swanky lawyer, and Catherine Zeta-Jones lights the place up as Velma, her newfound, scandalous best friend. They’re all entertaining, and they’re all almost eclipsed by John C. Reilly bringing down the house with “Mr. Cellophane.” Director Rob Marshall adds plenty of flash and fading dazzle but his large evasion of long takes betrays a lack of confidence in the physical and vocal abilities of the stars. The whole production feels like a giant put-on, a half-kidding exercise in capitalizing on brand recognition. With the athletic pizzazz and wonders of stagecraft leached from the adaptation, replaced by effects and attentive production design, Chicago comes off as a glittered-up trifle.

What Should Have Won: The Pianist

78) 'The Broadway Melody' (1929)


The Broadway Melody opens with an exquisite sequence, in which an owner of a musical think-tank of sorts passes through a hall with rooms filled with different musicians creating distinct sounds and melodies, ending with the man who pens the titular number. It’s all downhill from there in this amiable, impersonal musical about a pair of showgirl sisters (Anita Page and Bessie Love) who turn competitive when the entertainment business favors one over the other. The characters come off as primarily cyphers, representing a series of pretty familiar opinions of showbiz and entertainers in general, predictable even for the 1920s and 30s. As such, the movie comes off as nothing more than a vaguely competent musical with nothing much in the way of delights beyond the songs.

What Should Have Won: The Patriot

77) 'Braveheart' (1995)


How long will it be before Mel Gibson alienates us all again? My guess is about 18 months after President Donald Trump attends the premiere screening of Passion of the Christ 2: Resurrection Boogaloo. Maybe I’m letting my cynicism get the better of me here but Gibson’s obsession with the victimization of Christians has tainted his entire catalog, including Braveheart. As Gibson writes and portrays him, William Wallace is less a thoughtful yet violent revolutionary than a cypher for Gibson to express how reasonable, good, and not at all misinformed or ill-intentioned Christian folk are always chopped up, tortured, and executed by the greedy government and betrayed by the godless. Gibson is not interested in the complex political philosophies of Wallace or even the everyday toils of life under the rule of King Edward the Longshanks, only his makeup as a Christian martyr. His simplicity, even in its remarkably epic scope, disgraces a tremendous historical figure and carelessly milks outrage against those who don’t agree with Christians.

What Should Have Won: Babe

76) 'Mrs. Miniver' (1942)


William Wyler holds the title for the most nominated director in Oscar history and, for the most part, he deserves that title. To me, Wyler is the missing link between John Ford and Steven Spielberg, an artist capable of crafting masterworks but also egregiously docile prestige dramas. Mrs. Miniver lands in the latter category, unfortunately, but it benefits greatly from Wyler’s sharp, economic sense of visual storytelling. The story, about a British family dealing with life in the early days of Germany’s invasion of England, is lacking for intimacy and unremarkable, unwilling to see the ugliness, loss, and chaos of war and the effects of such conflicts at home. There are moments that are moving but Wyler’s film largely sticks to a far too familiar and biased perspective of World War II, the Oscars’ favorite subject by quite a margin.

What Should Have Won: The Magnificent Ambersons

75) 'West Side Story' (1961)


Let’s forget for the moment that gang warfare, even in the days when guns were less prevalent, wasn’t quite as romantic as this. Musicals, for the most part, have a tendency to excise the ugliness and bluntness of their subjects. The more unshakeable issue with this adaptation of Jerome Robbins and Arthur Laurents’ stage musical of the same name, itself an adaptation of Romeo & Juliet, is its classicism. Directed by Robbins and Robert Wise, West Side Story, which incorporates matters of race, crime, and class into its reminiscent narrative, is absolutely petrified of actually confronting those matters, even as it hints at their more illicit outcomes to drive its drama. The skill of the performers and the thrill of the music numbers is undeniable, but West Side Story never feels like the cinematic dream of anxious, angry youth that it should. Instead, Wise and Robbins’ colorful trifle comes off as nothing more than a mediocre musical unimaginatively transferred to the new environs of the big screen.

What Should Have Won: The Hustler

74) 'Cimarron' (1931)


This is a particular disappointment. Anthony Mann’s 1960 version of Cimarron depicts a brutal, unyielding emotional landscape that came from the land rush of the late 19th century in Oklahoma. It’s not a perfect movie – Mann’s venomous stylistic persona was watered down by co-director Charles Walters - but it’s one that palpably gets at the ugliness, violence, and unchecked ferocity that help bring America into the modern age. Wesley Ruggles' 1931 take, on the other hand, is a visually plain, if passable family drama that occasionally gets wrapped up in the bigger drama of an America coming together through rampant opportunism, theft, and corruption. Mann’s film remains stuck in your mind despite its flaws, whereas the 1931 version evaporates like steam the moment after it finishes.

What Should Have Won: The Front Page

73) 'Around the World in 80 Days' (1956)


Absolutely none of the thrilling, adventurous spirit of that powered Jules Verne’s exceptional novel survives in this bloated adaptation from John Farrow and Michael Anderson, he of Logan’s Run and The Quiller Memorandum. Though clearly hampered by the technology of the day, this would-be epic, clocking in at nearly three hours, is impressive for its wonky, expressive set and production design, as well as David Niven’s central performance as the playful and wise Phileas Fogg, but not much else at all. The warmth between Fogg and Passepartout (Cantinflas) feels tinny at best but even worse is the halted sense of action, a constant feeling of unending inertia. For a film that should be inflicted with curiosity, confidence, and a bear’s appetite for the unknown, Around the World in 80 Days more convincingly conjures the experience of sitting in a waiting room for that same amount of time.

What Should Have Won: Giant

72) 'Gigi' (1958)


Of all the movies that they could have nominated the great Vincente Minelli for, they had to award his artistry for one of his most empty and impersonal projects, a rare mediocrity in a career full of reflective, daring masterworks. Sure, the Academy also awarded the very good An American in Paris but that hardly assuages the issue. This musical, which follows the courtship between a wealthy Parisian bachelor and the titular young woman who captures his attention when so many other woman simply bore or disgust him, gave us one of the more famed renditions of Jacques Brel’s infamous “Thank Heaven for Little Girls.” That’s not a compliment. The entire film justifies lust for youth without considering the psychological pitfalls of the scenario, and never considers what it says about older men who chase after young women. For all the fanciful environs and set design, the film scurries past the idea that desire for youth tends to stem from a shattering fear of death. There’s no fear and little in the way of pain in Gigi, which makes its outlandish story of unlikely romance all the more unconvincing and surprisingly crude.

What Should Have Won: Cat on a Hot Tin Roof

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