Fox Searchlight Pictures

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

60

West Side Story (1961)

Pauline Kael famously had zero time for West Side Story, saying “it’s trying so hard to be great it isn’t even good,” and that “the bigger the leap the more, I suppose, the dancer is expressing—on the theory that America is a big, athletic country.” True, the merged sensibilities of co-directors Jerome Robbins and Robert Wise turned out a film that was both more overworked and more portentous than a musical about rival street gangs who work out their hostilities in dance offs ever should have been. And neither Natalie Wood, whose Puerto Rican accent flexes way beyond any dancer’s leap, nor Richard Beymer, sleepy and ineffectual as the former head of the Jets, clear much space around themselves as the romantic leads. Striving at every turn to transcend its genre rather than advance it, West Side Story nevertheless inherits a whole arsenal of strength from its source materials: Shakespeare’s Romeo and Juliet, Leonard Bernstein and Stephen Sondheim’s legendary Broadway score, Robbins’s mold-breaking choreography, and America’s dark, racist heart. Eric Henderson

What Should Have Won: The Hustler

All 90 Best Picture Oscar Winners Ranked

59

The Sting (1973)

If you believe the urban legend, filmmakers have been fooling audiences since at least the Lumiere brothers’ The Arrival of a Train at La Ciotat Station, a screening of which sent people scrambling from their seats as the moving image of a train steamed toward them on screen. The con at the core of George Roy Hill’s The Sting is a little more sophisticated than that: Johnny Hooker (Robert Redford) enlists veteran grifter Henry Gondorff (Paul Newman) to take down the brutal Irish gangster Doyle Lonnegan (Robert Shaw), who murdered Hooker’s mentor. Benefiting much from circumstance and luck, Hooker and Gondorff conspire to open up a fake betting parlor in an effort to bleed Lonnegan dry, financially speaking. There are elaborate conversations, apparent double-crosses, and costume changes aplenty. (Woe unto anyone who doesn’t pay strict attention during the first half hour or so, as the stakes for the scam are briskly outlined.) When this caper first opened, plenty of jaws probably dropped during its denouement, though not necessarily because of the filmmakers’ audacity. The Scott Joplin-soundtracked shenanigans collapse under their own weight, particularly if given a moment’s thought beyond the final fade-out. The Sting looks gorgeous, yes, but it ultimately proves to be as empty as the vacant building housing that fake betting parlor. Preston Jones

What Should Have Won: Cries and Whispers

All 90 Best Picture Oscar Winners Ranked

58

A Man for All Seasons (1966)

The staginess of A Man for All Seasons is evident in Fred Zinnemann’s direction, which uses slow zooms and roundtables of characters conversing to highlight the speech-laden screenplay, adapted from screenwriter Robert Bolt’s own stage play. Make particular note of the now famous scene in which Sir Thomas More (Paul Scofield) lectures Roper (Colin Redgrave) on man’s laws versus god’s laws; the sequence is cut to elevate More’s words as wise, even saintly, ensuring that the film works best as a showcase of its actors’ considerable prowess at chewing scenery. Robert Shaw, Wendy Hiller, Orson Welles, and John Hurt all give memorable performances, but the film itself is nothing revelatory and slags for much of its two-hour runtime. Pauline Kael said “there’s more than a little of the school pageant” in its rhythms. There’s also too little visual distinction to make this more than a creaky recipe for the studio prestige picture. Dillard

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

All 90 Best Picture Oscar Winners Ranked

57

The Sound of Music (1965)

For as empty an experience as The Sound of Music on film is, is it okay to admit that it’s Carmen compared to the stage incarnation? Every plot modification made by screenwriter Ernest Lehman (North by Northwest), every note of the enriched musical arrangements by Irwin Kostal, every coolly delivered, if still unimpeachably wholesome, line delivery by then Queen of the World Julie Andrews all combine to turn what was even then a creaky piece of manipulative flibbertigibbet into a reasonably agreeable way to pass the time with your older relatives, and even subtly reveals some of the play’s more unseemly undercurrents. This is, after all, the story of a man with seven children getting a very young, idealistic nun so hot and bothered she leaves the convent to be his female dear, who will respond to his every beck and call of “Do-Mi.” Eric Henderson

What Should Have Won: Darling

All 90 Best Picture Oscar Winners Ranked

56

Wings (1927)

Seen through the graph of the first Oscars, you can easily make heads or tails of the film’s strengths and weaknesses. In a pattern that would fade to oblivion after Gone with the Wind made the idea of a “sweep” not only possible but mandatory, the Oscars were given out like Cannes prizes, with films rarely taking more than a few statuettes, as if each award bestowed a just measure of validation. Wings won one of two “best movie” prizes, while the other (qualified as “Unique and Artistic Production”) was claimed by F.W. Murnau’s Sunrise, which has, by contrast, aged sublimely. Even though Oscar historians and statistic-heads generally put Wings on top, its prize is the more pedestrian-sounding “Best Picture, Production,” which is exactly right. It’s a producer’s triumph, an undeniably impressive marshaling of logistics, funds, and personnel, all at the service of an evening’s entertainment. More succinctly, it’s a philosophy of moviemaking and award-capturing that has never gone out of style. Christley

What Should Have Won: Seventh Heaven

All 90 Best Picture Oscar Winners Ranked

55

The Shape of Water (2017)

Though set in Baltimore in the early 1960s at the height of the Cold War, Guillermo del Toro’s The Shape of Water truly takes place in Movieland: that generic realm of borrowed fantasies where The Majestic and Amélie are also set. It’s been made with a level of craftsmanship that should be the envy of most filmmakers, but the impudent, unruly streak that so often gives del Toro’s films their pulse has been airbrushed away. Del Toro’s sentimental side takes over here, leaving the audience with a plot that fuses E.T. and Free Willy with a frustrated woman’s daydream of sexual salvation. Del Toro is aiming for critique via contrast, proffering a rosy vision of romantic acceptance that’s pointedly unpalatable to a real-life society governed by boundaries and biases. But such critique isn’t earned because del Toro isn’t willing to acknowledge uncertainty or emotional or moral fallibility on the part of his heroes, shifting all of humankind’s unsavory characteristics over to Strickland (Michael Shannon) and other American and Russian military personnel. Why doesn’t Elisa (Sally Hawkins), presumably romantically alone most of her life, feel terror once she’s found love? For all its conceits, themes, and symbols, The Shape of Water fails to impart a sense that its antique tropes have been adopted for a purpose. People, smitten with the film’s banalities, will claim that it has “heart.” But del Toro’s heart beats louder when he allows himself to play, dreaming his own dreams and respecting his heroes enough to sully them. Chuck Bowen

What Should Have Won: Phantom Thread

All 90 Best Picture Oscar Winners Ranked

54

Rocky (1976)

Blue-collar triumph reigns supreme in Rocky, a film that arguably created the sports movie clichés that have defined decades of American imitators, from Hoosiers to Rudy to We Are Marshall. Sylvester Stallone’s original formula, which follows a hungry young fighter in Philadelphia vying for his shot the heavyweight champion of the world, steals its use of streetwise dialogue and awkward passages of intimacy from other filmmakers, especially John Cassavetes, and molds it into a pandering crowd-pleaser. Rocky appeals to the dubious idea that human perseverance, particularly on the part of the underprivileged, is the solution to a society where momentary disadvantage is not so much baked into the culture as it is a matter of personal will. While other American filmmakers were pointing to the grimmer, systemic issues of media, racism, and political corruption, John G. Alvidsen is content to have his titular character quite literally wrap himself in the American flag. Dillard

What Should Have Won: Taxi Driver

All 90 Best Picture Oscar Winners Ranked

53

Slumdog Millionaire (2008)

Danny Boyle’s Slumdog Millionaire is a fairy tale of upward mobility in which the indefatigable Jamal’s (Dev Patel) devotion to protecting and—after his self-interested older brother, Salim (Madhur Mittal), becomes a murderous gangster and turns traitor on his sibling—reuniting with Latika (Freida Pinto) is predicated on unwavering faith in love. That destiny favors the pure of heart who are disadvantaged and romantic is an unabashedly mushy concept, and yet Boyle’s direction is ecstatic, enthralled by the notion that kindness and generosity in the face of hardship have a way of paying dividends in the most unexpected, circuitous ways. Jamal faces down two gangsters, the police, and a dastardly game show host on his way to Who Wants to Be a Millionaire’s 20-million rupee final question, an improbable path forged by an unwillingness to accept social standing as fixed that, eventually, unites him with the country of India at large. Schager

What Should Have Won: The Curious Case of Benjamin Button

All 90 Best Picture Oscar Winners Ranked

52

Oliver! (1968)

Based on Charles Dickens’s Oliver Twist, Oliver! survived the transplant from Broadway to screen about as well as any movie from its era. And even for as hopelessly behind the times it seemed circa 1968, maybe part of its appeal was in reminding a populace battered by political unrest, bloody assassinations, racial strife, and endless war that, hey, at least we’re not putting boys who ask for more gruel up for sale out on the cold, soot-ridden streets. Or beating the women who try to help them to death. So if the material seems unduly grim for the milieu, at least it delivers a score of memorable songs fit for whistling past the graveyard, and a stockade of grimed-up urchins popping their knees to Onna White’s precocious choreography. No one would ever die claiming this as Carol Reed’s finest hour, but on its own terms, it’s a reasonably well-oiled machine of a musical, if vaguely terrifying throughout. Eric Henderson

What Should Have Won: A Lion in Winter

All 90 Best Picture Oscar Winners Ranked

51

Patton (1970)

George C. Scott is Patton. In a career-defining performance, Scott embodied the controversial U.S. general in ways that have been equaled but never surpassed in the history of American biopics. Scott gets all of Patton’s rage, self-pity, arrogance, doubts and seemingly every other human emotion across in discreet chunks and sometimes all at once, capturing the modern-day gentleman warrior’s quixotic bravura, self-love, and misanthropy in equal measure. The screenplay, co-written by Francis Ford Coppola, has Shakespearean overtones, from soliloquies delivered in iambic pentameter on the eternal nature of war to ruminations on the difference (or lack thereof) between acting and being. This formal complexity is matched by the sheer scale and power of the battle scenes, which capture the brutality and amorality of the battlefield and hold up better than most war films from the time. But Patton is also a strange work for its time, an essentially pro-war film released at the height of the Vietnam War that glorifies an egomaniacal general precisely for his disregard for humanitarian notions like the wellbeing of his soldiers. It also glosses over his deep and abiding racism, particularly his anti-Semitism, as well as his dangerous warmongering after WWII. This out-of-placeness gives the film an uncanny quality, its undeniable visceral power masking an ethically retrograde core. Oleg Ivanov

What Should Have Won: Five Easy Pieces

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