Fox Searchlight Pictures

All 90 Best Picture Oscar Winners Ranked
All 90 Best Picture Oscar Winners Ranked


Terms of Endearment (1983)

It would be inaccurate to call this three-hankie classic, maybe the finest defense for the portmanteau “dramedy” that’s ever graced American screens, artless. On a Film Comment podcast about films designed to make their audiences cry, Mark Harris sagely pinpointed how the James L. Brooks production’s very first major laugh—as a young Aurora Greenaway (Shirley MacLaine, flawlessly prickly) crawls into her baby daughter’s crib thinking she’s stopped breathing and isn’t satisfied until she’s made the infant cry—encapsulates the entire central relationship in a nutshell. Still, the reason Terms of Endearment truly works is that Brooks’s comparatively loose and easy style give his actors the opportunity to breathe unexpected moments of real-life experience into their roles. Compare it to something like Steel Magnolias—in which Dolly Parton robotically declares “laughter through tears is my favorite emotion”—to see just how deftly Brooks avoids formula and achieves Parton’s emotional Valhalla. Eric Henderson

What Should Have Won: Terms of Endearment

All 90 Best Picture Oscar Winners Ranked


All the King’s Men (1949)

Pauline Kael once claimed that Willie Stark (Broderick Crawford), the folksy tin-pot despot at the center of Robert Rossen’s All the King’s Men, “might just make you feel better about the president you’ve got.” If only! In fact, Stark’s political graft, double-dealing, and sexual indiscretions all look a bit quaint in comparison to the shameless lies, bald-faced corruption, and vicious race-baiting of our current grafter in chief. But that doesn’t mean this pared-down adaptation of Robert Penn Warren’s Pulitzer Prize-winning novel lacks for insight into the warped psychology of U.S. politics. On the contrary, the film remains a compelling and surprisingly ambivalent study of a uniquely American demagogue: a hayseed bootstrapper turned thuggish autocrat who bellows populist slogans at throngs of whooping yokels like a cracker-barrel Mussolini. Crawford’s thunderous performance brings Stark to life, but it’s Rossen’s direction—which draws influence from the murky cynicism of film noir and the refractive realism of Citizen Kane—that ultimately makes the character so gripping. Rather than resolving the contradictions of Stark’s character, Rossen prefers instead to gape at him with a mixture of fascination and revulsion. Keith Watson

What Should Have Won: A Letter to Three Wives

All 90 Best Picture Oscar Winners Ranked


Gentleman’s Agreement (1947)

In a near-prophetic artistic gesture, director Elia Kazan presages and diagnoses the cult of social-issue martyrdom in the cinema as wholly well meaning but ostensibly shallow and unwise; the Potsdam Agreement and Hirohito’s surrender were, as major world events, barely settling into the social mindset and history at the time of the film’s release. Arguably Kazan’s first major work, Gentleman’s Agreement resonates with outrage and anguish, but its overarching thematic stronghold is far more fascinated in the importance and dangers of masquerade, the dividing yet highly permeable lines between façade and identity. And yet, Kazan smartly evokes and defends the power of narrative to summon truths thought largely intangible, as Schuyler Green’s (Gregory Peck) article on anti-Semitism is ultimately widely regarded as watershed writing, a coincidental prognostication of the film’s tremendously positive reception. The director, who emigrated to America from Istanbul and was brought up in the Greek Orthodox faith, clearly offers Green as his proxy, making Gentleman’s Agreement something like a fictional but sincere articulation of its making, but the tone of anger that rumbles beneath this whip-smart drama unmistakably comes from someone who knows all too well what it’s like to not be welcomed into the club. Cabin

What Should Have Won: Crossfire

All 90 Best Picture Oscar Winners Ranked


From Here to Eternity (1953)

Set against a backdrop of a military base in Hawaii in the weeks prior to the attack on Pearl Harbor, From Here to Eternity is about two men who die and two relationships that fall apart because three soldiers resist doing what would make their lives easier. The central cast of Burt Lancaster, Deborah Kerr, Montgomery Clift, Donna Reed, and Frank Sinatra showily perform their characters’ hatred for the paste that they try to fix with love or violence, sometimes both. Perhaps Director Fred Zinnemann himself gets a little too intoxicated with all the tragedy. The drama steadily grows into something just a little too big for the film’s meager narrative, sacrificing its coherence to the logic of the romances and passions on screen. But From Here to Eternity achieves its real intensity in the way it toys with and distorts its setting. Zinnemann’s bitter vision strips away the appeal of scenic Hawaii, turning it into a sinkhole, a place where passions swell but people quickly get stuck in place. Military life looks less like a model of personal discipline than a backwater of petty bureaucracy and personal abuse. In other words, Zinnemann frames the perfect setting for a story about self-destructive men and women yearning for a future with an ambiguous, probably impossible, promise of fulfillment. More than its iconic beach scene, then, the final moments summarize From Here to Eternity best: Reed and Kerr’s characters on a boat bound for the California, their dreams smashed to pieces. Whether life on the mainland will have more to offer them is anybody’s guess. Goldberg

What Should Have Won: From Here to Eternity

All 90 Best Picture Oscar Winners Ranked


Schindler’s List (1993)

This depiction of the wartime life of Oskar Schindler (Liam Neeson), a German entrepreneur who opened factories to help the Nazi war effort in Poland, only to staff them with Jewish workers, remains Steven Spielberg’s most personal film, but for different reasons than ancestry. Oddly triangulated between Schindler’s relationship with his workers, most prominently his accountant, Itzhak Stern (Ben Kingsley), and the brutal Nazi commandant Amon Goeth (Ralph Fiennes), the film allows Spielberg to study life in the ghetto, the concentration camps, and the Nazi aristocracy, but more potently dissects the limitations of fiscal success and artistic power, not to mention the valley that too often separates the personal and the logical. Spielberg has always aligned himself with the great and the burdened, and his connection with Schindler reveals a particular sadness in the director’s identity as a filmmaker. Spielberg’s indisputable talent has allowed him to put strong attention on domestic and international humanitarian issues while also crafting a number of hugely popular and successful entertainments, often utilizing the medium’s ability to preserve or recreate life and its philosophical promise of defying death to provide an optimist’s view of history. But that philosophical promise remains just that: a promise without a tangible reality. Schindler’s List is at once Spielberg’s doomed attempt to make good on that promise and a smart treatise on the essential impossibility of that promise. Cabin

What Should Have Won: The Piano

All 90 Best Picture Oscar Winners Ranked


You Can’t Take It with You (1938)

Tony Kirby (Jimmy Stewart), the son of snobs, falls in love with Alice (Jean Arthur), the daughter of free-spirited artists. Their relationship forms the core of this subversive romantic-comedy epic (126 minutes!), but the film is much bigger than the two of them, touching also on schemes involving real estate and munitions monopolies. Robert Riskin’s screenplay, based on a Kaufman-Hart play, treads themes that would later dominate director Frank Capra’s It’s a Wonderful Life: the evil that bankers do, and the importance of having friends who’ll take up a collection for you (in this case, neighbors, to pay a legal fine). But the villainous Mr. Potter-type isn’t played by Lionel Barrymore; Edward Arnold takes the role, while Barrymore plays his foil, the eccentric Grandpa Vanderhof, embodying anti-capitalist ideals in his apathy for money and his emphases on happiness and fun. He lords over a sort of commune dominated by several generations of his family and a few stray creatives: The house has a dancer, playwright, inventor, vibraphonist, fireworks manufacturers and more, including minstrel-y servants whose depiction is racist. Otherwise, they’re a delightful ensemble, loveable kooks bantering wittily, scrambling through screwball scenarios. But the squeaky Arthur, as Vanderhof’s granddaughter, dominates. She and Stewart are adorable together, as they seem to genuinely relish one another. Her eyes can simultaneously express love and loneliness; in fact, that’s her resting face, open and giving while pulling you into its yearning darkness. She’s irresistible. Stewart

What Should Have Won: Grand Illusion

All 90 Best Picture Oscar Winners Ranked


Marty (1955)

Played with heartbreaking vulnerability by Ernest Borgnine, Marty is the quintessential cinematic everyman, a lonely, insecure Bronx butcher resigned to bachelorhood but nevertheless secretly hoping to find a love of his own. When he meets the equally plain, lovelorn schoolteacher Clara (Betsy Blair), hope rises in Marty’s heart, only to be immediately quashed by the belittlement and criticism of those around him. In chronicling its proletarian protagonist’s struggle to find happiness, Marty shined a light on the regular people that went to the movies, reflecting their small hopes and dreams back to them with dignity and gritty humor. Borgnine channels the rough, primal energy that characterized his darker roles in earlier films into a measured performance of quiet despair and stoic solitude. There’s an underlying hint of self-loathing in his performance that gives the character an edge it might otherwise lack, endowing Marty with a moral grandeur worthy of Willy Loman and the other great, forlorn antiheroes of American tragedy. This small, humble character study, which also won the Palme d’Or at Cannes, brought a naturalism to the American screen that helped pave the way for the unsentimental realism of the films of the ’60s and ’70s. Ivanov

What Should Have Won: Marty

All 90 Best Picture Oscar Winners Ranked


The Deer Hunter (1978)

Coming as The Deer Hunter did just three years after the fall of Saigon, it’s unsurprising that Michael Cimino’s film plays like history written in lightning. Indeed, this fine-grained epic about what war does to men—blue-collar souls shredded beyond recognition in the damp, bloody jungles of Southeast Asia—derives considerable power from its sense of urgency. Thanks to the work of a formidable cast that includes Robert De Niro, Meryl Streep, and an Oscar-winning Christopher Walken, the film is greater than the sum of its parts—parts that have long been co-opted by popular culture, such as the harrowing Russian roulette scene. The steady accumulation of vivid details helps to give the film its cumulative power. It’s in the faces of a Russian Orthodox wedding’s attendees, in the grubbiness of the car that takes a group of men hunting, and it’s certainly in Steven Pushkov (John Savage) shrieking “Michael, there’s rats in here!” while stuck in a river (that Savage was actually screaming at Cimino, and not De Niro’s Michael, is beside the point). The 50-minute wedding sequence that opens the film is a masterful evocation of the home front as a kind of idyll, as well as a sharply detailed introduction to the group of soldiers who will go off to fight in a war that destroys their hearts and minds. Cimino’s film faced off against another Vietnam drama, Coming Home, at the Oscars and rightly prevailed on the big night, for this is a film that refuses to ever slip into the saccharine. Jones

What Should Have Won: An Unmarried Woman

All 90 Best Picture Oscar Winners Ranked


The Departed (2006)

With Michael Ballhaus’s coiled, constantly roving cinematography bringing a measure of unease to the underworld action, The Departed jumps out of the gate like a caged lion freed into the wild, delivering a rapid-fire primer on the congruent paths of state police academy trainees Billy Costigan (Leonardo DiCaprio), an intelligent recruit desperate to reject his family’s criminal past, and Colin Sullivan (Matt Damon), a careerist with political dreams and deep-seated ties to Costello. Sullivan is Costello’s mole in the police department and Costigan is the cop infiltrating Costello’s crew, and both are soon ordered to discover the other’s identity, a dueling-rats conceit William Monahan’s screenplay embellishes with trademark Martin Scorsese preoccupations: Catholicism, double lives, issues of honor, honesty, and deceit, and the bond shared between fathers and sons. Faithful to premise of Infernal Affairs, Scorsese’s adaptation nonetheless substitutes the original’s sleek, cool demeanor with a feverish, foul, funky energy that’s layered with a thin coating of sexual deviance (epitomized by Nicholson’s porn-theater dildo antics) and dysfunction (with Sullivan cast as the impotent son to Costello’s seriously virile papa). Deftly employing classic rock for clever commentary—never more so than with adjacent Nicholson and DiCaprio love scenes subtly linked by Pink Floyd’s “Comfortably Numb”—and swiftly crosscutting between multiple subplots, Scorsese’s film, for much of its 150 minutes, rocks violently, passionately, urgently. Schager

What Should Have Won: Letters from Iwo Jima

All 90 Best Picture Oscar Winners Ranked


Going My Way (1944)

In his BFI book on Boudu Saved from Drowning, Richard Boston argues that Groucho Marx could be seen as the author of his films, offering the following question as attempted evidence for his claim: “Without cheating, can you say off the top of your head who directed Duck Soup or any other Marx Brothers film?” Unfortunately for Boston, he’s asked cinephiles to name Leo McCarey, perhaps the most unique studio director of the 1930s. McCarey made better films than Going My Way, but few are as simultaneously warm and sharp, spinning its comedic yarn of two priests butting heads over their differences with an effortlessness that balances songs, visual gags, and dramatic conflict without forcing the film’s tone in one direction or another. In an era when Hollywood’s idea of fun involved navigating a maze of implied sexual interests and foregrounding vaudevillian performance styles, Going My Way remains among the most thoroughly accessible. Dillard

What Should Have Won: Double Indemnity