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 Scorsesesecured money for towering, radical masterworks likeThe Wolf of Wall StreetandSilencebecause of the Oscar love for one of his least ambitious works,The Departed. The lateJonathan Demme’s wins for his own masterpieces,PhiladelphiaandThe Silence of the Lambs, allowed him to continue a career defined by audacity in form and subject matter. The same could be said ofSpike Lee,Steven Soderbergh,Richard Linklater, and a number of other filmmakers that have defined the best of American filmmaking over the last few decades.
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 withThe Best Years of Our LivesorThe 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 asKathryn 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 ofMorgan 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 withJessica Tandy’s titular crank and her son (poorDan 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 Haggisat 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, andMichael 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 intoGreen 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 ofGreen Bookis 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 Bookis 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 byTom 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 toDustin Hoffmanfor devoting himself to a deeply wrong-headed character andBarry 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 Manbrandishes 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 Paltrowis 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-stealersGeoffrey Rush,Ben Affleck, and, yes, DameJudi 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 overTerrence Malick’sThe Tree of LifeandHugo, 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. DirectorMichel Hazanaviciusis 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 Artistfeels 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 theTrainspottingdirector 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 byMeryl Streep, who begins an intimate extramarital affair with an enigmatic hunk (Robert Redford) in Kenya. On the other hand, it’s directed by the lateSydney 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, butKramer vs. Krameris 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 NoworAll That Jazz
82) ‘A Man for All Seasons’ (1966)
The quasi-lead performance fromRobert Shawis the sweet, syrupy plum amongst a lump of bland porridge here. TheJawsactor’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 byPaul Scofieldas Thomas More,Orson Welles,Wendy Hiller,John Hurt, andSusannah York. They all take great glee in diggint intoRobert 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 directorFred Zinnemannwould 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?


