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This story has been updated to reflect the events of the 92nd Annual Academy Awards.

Whatever your opinion of the Academy Awards, if you care about film, you can’t just dismiss them. If nothing else, the Academy’s winners double as a history of film. An imperfect history, sure, but a history nonetheless. Running through the list of Best Picture winners, you’ll see trends wax and wane and at least get a rough sense of what was valued in movies for each year and the progression of trends. Around the World in 80 Days’ Best Picture win, for instance, looks like the pendulum swinging back from the grit of On the Waterfront and Marty, the previous years’ winners.

But what if each year produced two winners? Madness, right? But it would have the advantage of offering a fuller picture of what was going on in the world of film at the time.

This list attempts to do just that: Pick a second film from the list of Best Picture nominees that would both make for a deserving winner and offer a fuller sense of film history. It’s not an attempt to pick a winner from the year in its entirety. (Though Danny Peary’s 1993 book Alternate Oscars proves there’s a lot to be learned from doing that.) It’s not an attempt to suggest that these films are better than the films that won, even if they sometimes are. (Ahem, Crash. Ahem, Braveheart.) It’s an attempt to identify each year’s best Best Picture loser, perhaps suggest a film that could deservingly sit beside the winner as a fine second choice. Consider it an alternate path through Oscars history. So let’s start from the very beginning, back when winners were announced in advance and the awards ceremony consisted of an elaborate dinner.

1st Academy Awards: 1927/28

Winner: Wings

Best Loser: Sunrise

The 1st Academy Awards makes choosing an accompanying Best Picture winner easy: The Academy officially chose one for itself. For one year only, the Oscars selected both an “Outstanding Picture” and a “Best Unique and Artistic Picture.” The idea was to distinguish more commercial films from more artistically inclined efforts (shades of the controversial Outstanding Achievement in Popular Film prize announced, then dropped, in 2018). Retroactively, Outstanding Picture winner Wings was named as that year’s Best Picture winner, consigning Sunrise: A Song of Two Humans to a footnote, if only in terms of awards history. Yet Sunrise is a stunning achievement that could just as easily have taken the honor. The story of an unnamed man (George O’Brien) and woman (Janet Gaynor, who won Best Actress for her work here) in a state of marital discord, it finds F.W. Murnau bringing the German Expressionist techniques he pioneered with films like Nosferatu and The Last Laugh to Hollywood. It’s decidedly, to use the Academy’s terms, unique and artistic, though whether that puts it into a different category than a more popular film like William Wellman’s high-flying Wings remains a surprisingly lively question this deep into the Oscars’ existence.

2nd Academy Awards: 1928/29

Where Sunrise would come to typify the sort of film that usually wins Best Picture — a serious artistic statement from a major director — In Old Arizona typifies the sort of film that would rarely take the top prize in the future, an unpretentious, crowd-pleasing genre film (albeit one that builds to an unexpectedly grim ending). It still works pretty well on those terms, though enjoying it now means looking past the sight of heavily made-up white actors playing Latino characters. Still, this adaptation of an O. Henry story tilts all its sympathies toward the outlaw hero the Cisco Kid (Warner Baxter, in a Best Actor–winning role) and away from the pompous white soldier charged with tracking him down. The popularity of the film would help make Cisco Kid a movie, radio, pulp, comics, and TV staple for years to come, played several more times by Baxter, then later by Cesar Romero and, most recently, Jimmy Smits.

3rd Academy Awards: 1929/30

The prison drama The Big House performs a similar sleight of hand, setting up a new prisoner sent up on a manslaughter charge after a drunk-driving incident (a young Robert Montgomery) as the hero, but focusing instead on a pair of hardened criminals (Chester Morris and Wallace Beery) who turn out to be not as irredeemable as they first appear. A highly influential film that set the pattern for prison movies to come, it’s a gripping piece of filmmaking, filled with images of how prisons dehumanize those within its bars, that builds to a violent climax that still looks pretty shocking.

4th Academy Awards: 1930/31

The only problem with The Front Page is that Lewis Milestone’s adaptation of Ben Hecht and Charles MacArthur’s play about fast-talking journalists on the crime beat will always be overshadowed by Howard Hawks’s even better His Girl Friday, a take on the same material but with a gender flip that makes it do double duty as a romantic comedy. But Milestone’s film is no small accomplishment either. Starring Adolphe Menjou and Pat O’Brien, it’s fast-paced and funny and finds the director doing his best to break past the limitations of the early sound era and bring visual flair to the dialogue-driven material.

5th Academy Awards: 1931/32

Speaking of visual flair, Josef von Sternberg didn’t abandon the stunning visual style he developed in the silent era once sound entered the picture. He also picked up an ideal collaborator in the form of Marlene Dietrich, an actress who understood just how powerfully she could hold the screen with a world-weary look and a breathtaking costume. Shanghai Express is the fourth of seven films that Dietrich made with Sternberg between 1930 and 1935. Set in a China in the midst of political turmoil, it stars Dietrich as a “coaster” — a woman of questionable reputation who moves among the men of the ruling class — who unexpectedly reunites with the man she truly loves on a train destined to be taken over by revolutionaries. Sternberg and Dietrich’s partnership thrived in the pre-Code era, and the film mixes unforgettable images with a complicated depiction of sexual mores that wouldn’t fly a few years later.

6th Academy Awards: 1932/33

Nor, for that matter, would 42nd Street, a behind-the-scenes musical drama about the tough business of putting on a show during the Depression that doesn’t hide the rough edges or turn its characters into saints. (Ginger Rogers, for instance, plays a heroine nicknamed “Anytime Annie.”) This early in the sound era, movies were still figuring out what musicals could be. But they didn’t want for talented creators with big ideas, including Busby Berkeley, who directed the film’s musical sequences. Berkeley understood that there was more to a movie musical than pointing a camera at performers and letting it roll, that the camera itself has to be part of the choreography, and that sense is already very much in place in this early effort of what would turn out to be a long career.

7th Academy Awards: 1934

Frank Capra’s road movie/romantic comedy It Happened One Night became the first film to sweep the Oscars in every major category, dominating the awards so thoroughly that seemingly nobody else had a chance. It was also a too rare instance of a comedy taking the top prize, though the charming romantic mystery The Thin Man — starring Myrna Loy and William Powell as a crime-solving couple who love mystery, alcohol, their dog, and each other — wouldn’t have been a bad choice either. The film kicked off a delightful series, but this first entry is the sharpest and best, with Loy and Powell’s sexual chemistry and bons mots drowning out virtually any other aspect of the film — not that that’s any reason to complain.

8th Academy Awards: 1935

The plot of Top Hat is the flimsiest of farces in which a string of misunderstandings keep Fred Astaire’s and Ginger Rogers’s characters from getting together until the film’s final moments. It’s also a pure delight, with Astaire and Rogers at their most charming as they dance their way through a string of missed connections and moments of mistaken identities to a series of songs written by Irving Berlin. The pair appeared together in ten films, and though both had tremendous success apart from one another, there’s a kind of magic to seeing them together. Top Hat surrounds them with colorful characters, drops them into lush sets, and lets that magic happen.

9th Academy Awards: 1936

Adapted from a Sinclair Lewis novel subsequently turned into a successful play, Dodsworth stars Walter Huston and Ruth Chatterton as a retirement-age couple who get to know each other again while traveling to Europe, only to learn that they don’t relish each others’ company anymore. The film wouldn’t work with a director who couldn’t focus intensely on the inner lives of its characters. Fortunately, it had William Wyler, who knew how to pull that off better than virtually anyone else, via a combination of assured, understated filmmaking and a reliance on strong performances. Wyler already had dozens of films to his credit when he made Dodsworth, but it’s with this film here that he earned the first of many Oscar nominations.

10th Academy Awards: 1937

The Oscars fell into hard-to-break patterns fairly early in its existence, one of them being a tendency to take serious films more, well, seriously than comedies. It Happened One Night’s multi-category sweep a few years earlier and Capra’s second Best Picture triumph for 1938 would prove notable exceptions, and Leo McCarey’s screwball comedy The Awful Truth — in which Cary Grant and Irene Dunne figure out that maybe getting divorced isn’t such a hot idea after all — probably didn’t stand a chance up against the likes of A Star Is Born, The Good Earth, Lost Horizon, and the ultimate winner, The Life of Emile Zola. It’s a sterling example of the form, however, and Grant and Dunne make ideal sparring partners, so ideal that they’d appear in two more films together.

11th Academy Awards: 1938

Another bad habit for the Academy: only occasionally remembering that great films are often made in countries that don’t speak English, efforts usually relegated to the Best Foreign Language Film category. That category wouldn’t even be introduced until 1947, but at least the awards for 1938 acknowledged the existence of Jean Renoir’s Grand Illusion, a humanistic story of the first World War released as a second such war loomed on the horizon.

12th Academy Awards: 1939

Every once in a while there’s a year that’s home to more enduring classics than most years. Sometimes the Best Picture nominees don’t reflect this. (The nominees for 1999, for instance, leave out Being John Malkovich, Magnolia, The Matrix, Fight Club, The Talented Mister Ripley, Boys Don’t Cry, The Iron Giant … the list goes on.) But sometimes they do. Gone With the Wind — a giant cultural phenomenon if nothing else — beat out Dark Victory, Mr. Smith Goes to Washington, Ninotchka, Of Mice and Men, Stagecoach, The Wuthering Heights, Goodbye Mr. Chips, and Love Affair to win Best Picture. It also beat out an equally, if not more, enduring film from director Victor Fleming: The Wizard of Oz, which has since become several generations’ first bewitching introduction to both musicals and classic Hollywood filmmaking.

13th Academy Awards: 1940

1940 wasn’t quite 1939, but it still produced more timeless movies than most years. Both Alfred Hitchcock and John Ford directed two Best Picture nominees (Hitchcock’s Rebecca took the prize) and with The Philadelphia Story, George Cukor delivered one of the greatest romantic comedies. But if we want this list to double as a shadow history of other trends in Oscar-nominated films, let’s give this slot to The Great Dictator, both because Charlie Chaplin isn’t represented anywhere else — on this list or the list of actual winners — and because nobody else was making a film like it in 1940. Even after the outbreak of World War II, Hollywood wasn’t rushing to make films condemning Hitler; Chaplin served as his own producer for the film, in which he plays the dual roles of fascist dictator Adenoid Hynkel and his look-alike, an unnamed Jewish barber who gets swept up into the ugly business of authoritarianism. It was a risky undertaking, mixing absurd humor with biting satire in the service of a heartfelt plea for peace, but it became a hit with critics and audiences alike.

14th Academy Awards: 1941

How Green Was My Valley beating out Citizen Kane — for years the consensus choice for the greatest film ever made — to win Best Picture is one of the easiest examples to point to of Oscar getting it wrong. This overlooks two facts: (1) How Green Was My Valley is also pretty great, and (2) the competition was tough that year, which also saw nominations go to Here Comes Mr. Jordan, The Little Foxes, The Maltese Falcon, Sergeant York, and Suspicion, among others. (The Academy would cap the nominee number at five a few years later, and it would stay that way until 2009.) That said, none of those movies are Citizen Kane, first-time director Orson Welles’s rise-and-fall story (co-scripted by Herman Mankiewicz) inspired by the life of William Randolph Hearst and filled with every filmmaking trick Welles knew (and many he invented).

15th Academy Awards: 1942

1942 was another year with an abundance of great Best Picture nominees (Yankee Doodle Dandy and The Pride of the Yankees among them), yet it still makes the most sense to choose an Orson Welles film as our alternate. The Magnificent Ambersons was taken out of Welles’s hands before he finished it, setting him up to have high-profile conflicts with studios and producers for the rest of his career. The tacked-on ending still sticks out, but the depiction of a midwestern family’s dimming prospects and fading optimism is both endlessly inventive and deeply affecting.

16th Academy Awards: 1943

When David O. Selznick made a big push for the 1946 film Duel in the Sun, Variety dismissed it as a “glorified Western.” The genre wasn’t held in universally low esteem — Cimarron won Best Picture; Stagecoach and others earned nominations — but talking of it dismissively didn’t exactly raise any eyebrows either. Such was the uphill battle faced by Westerns even at the height of their popularity. But even the most snobbish viewer could see that William Wellman’s The Ox-Bow Incident was no ordinary Western. A story of mob mentality taken to a deadly extreme, it stars Henry Fonda as a cowboy who joins a posse to track down some murderers only to watch as its pursuit of justice spins out of control. The prolific Wellman directed Wings, the first Best Picture winner, and here seizes on the story’s timelessness and helps set the stage for the morally ambiguous Westerns that would dominate the 1950s.

17th Academy Awards: 1944

Billy Wilder and co-writer Raymond Chandler didn’t create film noir with this adaptation of a James M. Cain story about an insurance agent (Fred MacMurray), a femme fatale (Barbara Stanwyck), and the murderous scheme they embark on together. But film noir certainly wouldn’t have been the same without the combination of Wilder’s sour take on humanity and Chandler’s dialogue. The Academy was more in the mood for uplift, honoring Going My Way, in which Bing Crosby plays a laid-back priest. But it’s Wilder’s film whose influence would seep into the groundwater.

18th Academy Awards: 1945

Did any director thrive in the studio system quite as much as Michael Curtiz? Born in Hungary, Curtiz enjoyed great success in the European film industry, and then even greater success when he became Warner Bros.’s No. 1 in-house director, a stint that included Casablanca, a long association with Errol Flynn, and more. Curtiz was meticulous and adaptive and at first none-too-thrilled to be working with Joan Crawford, who needed a comeback and to prove her worth to Warner Bros. when she landed the lead in Mildred Pierce. She achieved both aims, and won over Curtiz, with this noir-influenced James M. Cain adaptation about a mother who gives and gives to a daughter who takes more than she deserves. It’s an example of every piece of the studio machinery working in perfect sync — from the star to the shadow-drenched compositions — to create art as heartbreaking as it is thrilling.

19th Academy Awards: 1946

World War II upended the professional lives of both director Frank Capra and actor James Stewart. Capra focused on making morale-boosting documentaries about the war. Stewart fought, returning shaken by his experiences as an airman. He would rarely discuss his time in the service in later years, and he struggled to resume acting, pausing before accepting the role of George Bailey, the small-town savings-and-loan proprietor who comes to realize how much his life has touched those around him. The film underperformed at the box office, only becoming a Christmas staple years later after a copyright lapse led to near-constant airings on local stations in the ’70s and ’80s. It didn’t lack for plaudits at the time, however, earning five Oscar nominations, including a Best Actor nod for Stewart and a Best Director nomination for Capra. It lost them all to The Best Years of Our Lives, another thoughtful consideration about what really matters, similarly informed by the war years. They now make a satisfying double feature.

20th Academy Awards: 1947

David Lean wouldn’t win any Academy Awards until he became the go-to architect of thoughtful epics like Bridge on the River Kwai and Lawrence of Arabia. But he might just as rightly have won for this adaptation of Charles Dickens’s Great Expectations, which streamlines the novel without losing Dickens’s clever plotting, rich characters, or flair for grotesquerie. Its nomination provided another sign that the British film industry remained alive and well in the years after World War II — to say nothing of what was happening in Italy, Japan, France, Sweden, and elsewhere. More would follow.

21st Academy Awards: 1948

We can probably thank The Red Shoes for inspiring an entire generation of dancers, and it’s not hard to see why. Its story about pursuing artistic perfection no matter what the personal cost goes to some tragic places, but there’s so much beauty along the way that it almost seems worth it. That ambiguity is at the heart of Michael Powell and Emeric Pressburger’s story, which centers on a ballerina who struggles to reconcile her need to pursue her artistic gifts with her desire for happiness. Powell and Pressburger were pushing boundaries as well, blurring the lines between filmmaking and choreography — and reality and dreams — in the stunning dance sequences and making bold use of Technicolor in ways never attempted before. It’s a tale of obsession made with obsessive attention to detail and a stunning command of film’s power to stir and move.

22nd Academy Awards: 1949

A case of a clever idea elevated by a thoughtful filmmaker and a perfect cast, A Letter to Three Wives gives viewers three stories of unsettled marriages for the price of one. Originally based on the novel A Letter to Five Wives before being trimmed (at one point Anne Baxter was to have played a fourth wife), it opens with three wives (Jeanne Crain, Ann Sothern, and Linda Darnell) receiving a letter from a never-seen friend informing them that she’s leaving town with one of their husbands. As the day passes, each reflects on whether or not it could be her husband — and whether or not she should blame herself if it is. It’s a rich setup that Joseph Mankiewicz uses to depict the domestic discontents beneath the surface of postwar American prosperity.

23rd Academy Awards: 1950

There’s long been a strand of self-loathing to the film industry, and sometimes that self-loathing leads to great movies. It’s evident in All About Eve, a film about the cutthroat world of Broadway that could just as easily have been about Hollywood. And it’s essentially the raison d’être of Billy Wilder’s equal parts tragic and darkly funny Sunset Boulevard, in which a struggling screenwriter (William Holden) discovers Hollywood’s gothic underbelly after stumbling into an intense relationship with an unstable star of the silent age (Gloria Swanson). Swanson’s own history — she’d been one of Paramount’s biggest stars but had struggled professionally since her heyday — is just one way the film holds a dark mirror up to the town that made it possible.

24th Academy Awards: 1951

Adapting Theodore Dreiser’s An American Tragedy, George Stevens chose to focus on the interior lives of its characters: a striving factory worker (Montgomery Clift), the co-worker he romances and impregnates (Shelley Winters), and the smart-set object of desire (Elizabeth Taylor) who leads him to make some cruel choices. Powered by intense performances and Stevens’s craftsmanship, it’s powered by the tension between its raw emotions and the artfulness of their presentation — the same combination that powered another nominee that might just as easily have taken the year’s Best Picture prize, A Streetcar Named Desire.

25th Academy Awards: 1952

A Western in which the hero spends much of the film fearing for his life, unable to rally those he’s sworn to protect to help him in spite of the righteousness of his cause, High Noon didn’t fit the genre’s usual mold, and it didn’t please all of the genre’s admirers. Howard Hawks has said he made Rio Bravo as a response to the film, turned off by the seeming helplessness of the hero, played by Gary Cooper. But the Fred Zinnemann–directed film struck a chord with audiences and critics alike, many of which did not miss that its central conflict mirrored the paranoia of the McCarthy era. But though it won four Oscars, including a Best Actor prize for Gary Cooper, controversy surrounded it thanks to the hounding of screenwriter Carl Foreman for taking the fifth before HUAC. (Among those doing the criticizing, John Wayne, who’d turned down the Cooper role and whose The Quiet Man was also nominated for Best Picture that year.) Foreman ended up blacklisted and Cecil B. DeMille’s popular, if little loved, The Greatest Show on Earth took the top prize.

26th Academy Awards: 1953

The film that made Audrey Hepburn a movie star, Roman Holiday is the ideal to which all romantic comedies aspire, and builds to a lovely, bittersweet ending that few have dared to duplicate. Hepburn plays Ann, a princess who sneaks away from her handlers and gets to explore Rome in the company of Joe (Gregory Peck), a worldly reporter who at first doesn’t recognize her, then conspires to exploit the friendship — an instinct that lasts until he realizes that he’s falling for her. Co-scripted by a long-uncredited Dalton Trumbo, it’s both a love letter to Rome and distillation of what it feels like to fall unexpectedly in love, even when there’s little hope of that love lasting beyond the length of a fling.

27th Academy Awards: 1954

Humphrey Bogart became famous by playing a certain type of cool, hard-bitten character, but he created some of his best performances by tweaking his onscreen persona. In a Lonely Place, for instance, finds him plumbing the darkness beneath the surface of a hardened loner. And in The Caine Mutiny, he portrays a naval captain who cracks in slow-motion, his air of authority hiding the rage and paranoia that drives him. There’s much to recommend in Edward Dmytryk’s adaptation of Herman Wouk’s novel, about a mutiny and its ensuing court martial in the midst of World War II, but it’s Bogart’s haunting work that makes it unforgettable.

28th Academy Awards: 1955

To continue the theme of naval rebellion: Henry Fonda spent years playing the lead of Mister Roberts on Broadway — so long, in fact, that by the time this film adaptation came around, some considered him too old, and too long out of movies, to play the part. But the film suggests no one else could have played it half as well, pitting Fonda’s Roberts, a junior-grade naval lieutenant, against a tyrannical captain played by James Cagney as they work an unglamorous assignment during World War II. The film’s a strange but potent mix of irreverence and patriotism. Roberts wants to fight but is kept away from the war by his dull commanding officer’s whims, so he retaliates with insubordination. It has a tattered origin, too. John Ford directed it until illness and conflict drove him away, leading to Mervyn LeRoy and an uncredited Josh Logan taking over. (Logan, co-writer of the theatrical version, also directed another 1955 Best Picture nominee, Picnic.) But the humor keeps it lively from beginning to end, and the performances — including a Best Supporting Actor–winning turn from Jack Lemmon — are priceless.

29th Academy Awards: 1956

George Stevens won his second Best Director prize for Giant, a sprawling story of oil, Texas, racism, and thwarted passion starring Elizabeth Taylor, Rock Hudson, and (in his final role) James Dean. Yet it wasn’t enough to overcome the publicity blitz created by producer Mike Todd for his star-packed adaptation of Jules Verne’s novel. (That Todd was married to Taylor added an extra twist to the tale.) Nonetheless, in the middle of a decade in which prestige pictures often emphasized bigness, Giant remains a model of how to tell an intimate story on a grand scale, focusing on the lives of a handful of characters without letting them become dwarfed by the landscape or the extended running time.

30th Academy Awards: 1957

The film industry saw television as a threat from the moment it was introduced, and spent much of the ’50s trying to create new ways to compete with the new medium on the block, from wide-screen movies to 3-D. But TV and film found that their coexistence could be mutually beneficial, with television sometimes serving as a proving ground for film material and a new generation of film directors honing their skills on the small screen, where they learned to work fast and make the most of a few sets and limited budgets. 12 Angry Men benefited from both those trends, adapting a previously produced teleplay and serving as the feature-film debut of Sidney Lumet, who’d worked extensively in television. Lumet and a remarkable cast headed by Henry Fonda create high drama as jurors arguing a case that all but Fonda’s character sees as open-and-shut — leading him to dig in in an attempt to make everyone else see it his way.

31st Academy Awards: 1958

Producer and director Stanley Kramer’s name has become synonymous with righteous films about pressing social issues, and while that’s not entirely unfair, it doesn’t quite capture the variety of films that bear his name, from High Noon, The Caine Mutiny, and The Wild One (which he produced) to It’s a Mad, Mad, Mad, Mad World, an attempt to make comedy on an epic scale. The Defiant Ones is, literally and figuratively, one of his most bare-knuckled efforts, chaining Sidney Poitier and Tony Curtis together as escaped prisoners and forcing them to work out their differences if they want to survive. The film deals with prejudice by folding it into a propulsive chase movie, letting the politics serve the narrative and not the other way around. Kramer didn’t always get that balance right, but it works here.

32nd Academy Awards: 1959

Otto Preminger was no stranger to taboo-smashing when he made Anatomy of a Murder, having previously directed The Moon Is Blue — scandalous for its then-shocking discussion of sexuality — and The Man With the Golden Arm, which dealt frankly with drug addiction. The legal thriller Anatomy of a Murder was no exception, shocking audiences with a courtroom drama filled with graphic discussions of rape. That it was Jimmy Stewart as a laid-back lawyer doing much of the talking only made it more shocking, and the film was even banned for a time in Chicago. Once smashed, taboos have a hard time being restored, and its straightforward approach to adult material helped set the stage for the decade to come, one in which the once-inescapable Motion Picture Production Code would first lose power before being replaced by the modern ratings system.

33rd Academy Awards: 1960

Robert Mitchum rarely got to show his gentler side, but it’s on full display in this Fred Zinnemann–directed story about Irish-Australian settlers living a peripatetic existence along Australian frontier. Mitchum plays a man whose wanderlust is challenged by the needs of his wife (Deborah Kerr) and son, and Zinnemann’s beautiful shots of the Australian wilderness make it easy to see why anyone would find it hard to stay in one place. It’s a film of high stakes, if little overt drama, highlighted by Peter Ustinov’s comic supporting turn. Those qualities might have made it easy to choose a masterpiece like The Apartment over it, but it remains an involving story of a family’s by turns joyful and perilous existence.

34th Academy Awards: 1961

A tale of moral compromise and the heavy price of success set in the seedy world of competitive pool, Robert Rossen’s The Hustler earned nine Academy Award nominations, and gave Newman one of his most famous roles, one he’d revisit years later in The Color of Money, for which he’d finally win a Best Actor trophy after six nominations. The film became a hit unexpectedly, its success spurred in part by rave reviews and a sense that the film knew the ins and outs of the world it was depicting. (That Rossen had once hustled pool probably helped.) Though shot in Cinemascope, it’s defined by a sense of claustrophobia. These are characters who always feel like the walls are about to close in on them. Often they’re right.

35th Academy Awards: 1962

It’s not hard to see why Gregory Peck’s performance as Atticus Finch has become synonymous with unbending American virtue in the face of fierce opposition. Peck plays Finch as a man with a deep sense of right and wrong, but also as someone capable of deep disappointment, someone who struggles with how to convey the injustice of life to his children. Like the film around him and the Harper Lee novel from which it’s adapted, he’s hopeful but clear-eyed, aware of how hard it is to champion justice and tolerance in a world that often seems to want neither.

36th Academy Awards: 1963

The concept of “too big to fail,” coined for the banking system, can extend to movies, too. Cleopatra was a notorious flop in 1963, but that didn’t stop it from winning a Best Picture nomination anyway. It’s worth seeing if only to see what all that money looks like on the screen, but for a better example of Hollywood going big — in the most literal sense — check out How the West Was Won, a star-filled omnibus film directed by John Ford, Henry Hathaway, and George Marshall that charts the progress of Western expansion via a series of loosely related stories. Its full effect will be lost on even the biggest home screen, however. It’s the most ambitious film shot in true Cinerama, a process involving three cameras, three projectors, and an arcing screen that creates an immersive quality rivaled only by IMAX. It’s a good movie, but an even better spectacle.

37th Academy Awards: 1964

Stanley Kubrick set out to make Dr. Strangelove as a straight thriller, but the deeper he got into the project, the more absurdity he saw in Cold War politics and the careful balancing act needed to keep a policy of mutually assured destruction from tipping over into a nuclear apocalypse. The result — an obsidian-black comedy in which Peter Sellers plays multiple roles — depicts a crisis set in motion by the one man’s cracked mind, but kept in motion by the insane systems around it. It’s filled with comic high points, but it’s the queasy sense that the fate of the world has never been more perilous that makes it haunting — now as much as ever.

38th Academy Awards: 1965

Seeing the biggest movies of 1965 meant sitting still for a while. The winner, the Julie Andrews–starring musical The Sound of Music, clocks in at 174 minutes. Doctor Zhivago, which tied it with five nominations, runs 193 minutes. Director David Lean didn’t want for Oscar success, having taken both Bridge on the River Kwai and Lawrence of Arabia to Best Picture wins and winning Best Director for both, but here the Academy ultimately went with the lighter option with The Sound of Music, a box-office smash that didn’t do much for critics at the time. The years have been kind to The Sound of Music, but there would have been no shame in giving Lean a third win for his sweeping story of upheaval in Russia starring Omar Sharif and Julie Christie, an emerging star who’d win Best Actress for a different Best Picture nominee, the stylish British morality play Darling.

39th Academy Awards: 1966

In filmmaking, there are big risks and small risks. Taking a shockingly profane Edward Albee play about one long, dark night in the lives of a hard-drinking middle-aged couple — and handing it over to a first-time director — is itself a pretty big risk. Casting married movie stars who seemed at first too young and glamorous for the parts only made it more risky. But with his adaptation of Who’s Afraid of Virginia Woolf?, Mike Nichols showed audiences something they’d never seen before, stripping away the glamour from Elizabeth Taylor and Richard Burton and letting their harsh words draw blood as they spend an evening with a younger couple who gets drawn into the emotional quicksand around them. The risk paid off with a nomination, though not a trophy, and helped push the boundaries of what was permissible in movies in ways that would never be pushed back.

40th Academy Awards: 1967

Containing everything from talking animals to amoral criminals, the nominees for 1967 double as a cross-section of what was going on in Hollywood at the time, so much so that Mark Harris used it as the subject for his excellent book Pictures at a Revolution. Filtering a story of prejudice through a tense thriller set in the Deep South, In the Heat of the Night took the top prize. Elsewhere, both The Graduate and Bonnie and Clyde captured a Hollywood filled with fresh ideas, the product of an emerging generation of new filmmakers and the influence of the French New Wave. Of the two, Bonnie and Clyde is the more radical, and its violent antiheroes — Warren Beatty and Faye Dunaway playing a pair of notorious Depression-era outlaws — made it the more controversial, so let’s make it our alternate choice and let it serve as a stand-in for the seismic changes going on around it.

41st Academy Awards: 1968

Sometimes the Best Picture field is defined by what it leaves out. 1968 could have seen nods for 2001: A Space Odyssey, Faces, Rosemary’s Baby, or any number of other challenging films. Instead, the Academy played it safe, awarding the splashy Dickens musical Oliver! and not getting all that adventurous with the nominees, either. The Lion in Winter, in which Peter O’Toole’s Henry II and Katharine Hepburn’s Eleanor of Aquitaine argue over who should succeed him as King of England, proved controversial in part because it looked like such a safe choice, even prompting several critics to resign from the New York Film Critics Circle after it won that prize. Groundbreaking it’s not, but O’Toole and Hepburn (who’d win her second Best Actress prize for her work) are remarkable and the film’s sharp exchanges give it an electric charge that makes it anything but staid.

42nd Academy Awards: 1969

The breakout success of Easy Rider marked a turning point that would help define the next decade of films, a shaggier period less beholden to the old ways of doing things. The Best Picture nominations overlooked it, as well as another sign of things to come, Sam Peckinpah’s ultraviolent Western The Wild Bunch. But another Best Picture nominee offered a more playful variation on The Wild Bunch’s elegiac spirit, the George Roy Hill–directed Butch Cassidy and the Sundance Kid, starring Paul Newman and Robert Redford as outlaws roaming an Old West that’s starting to leave them behind. Scripted by William Goldman, it used one of film’s most venerable genres to explore the idea of changing times as a turbulent decade drew to a close.

43rd Academy Awards: 1970

The 43rd Academy Awards provided even more evidence of the upheaval happening in the movie business. In the Best Picture category, hip and irreverent New Hollywood films like M*A*S*H and Five Easy Pieces vied with the cornball Airport and Love Story (even if the latter dressed up its sappy narrative with New Wave–inspired filmmaking). The winner, the sharp biopic Patton, belonged to neither camp, but Five Easy Pieces — a Bob Rafelson–directed film fueled by the restlessness and discontent of the ’60s, in which Jack Nicholson plays a man who believes he doesn’t fit in anywhere — would have represented the changing times.

44th Academy Awards: 1971

Peter Bogdanovich made his feature directorial debut in 1968 with the inventive, low-budget thriller Targets, but his meteoric ascent began a few years later with this Larry McMurtry adaptation about a small Texas town and the reckless youth that call it home in the early 1950s. Bogdanovich grew up idolizing (and later often befriending) the directors and actors of classic Hollywood, but he never slavishly imitated them. Instead, he made films that bridged the gap between new and old. Shot in black-and-white and filled with images influenced by classic Westerns, The Last Picture Show pays homage to Bogdanovich’s influences but has a restless, New Hollywood energy and downbeat tone, all its own.

45th Academy Awards: 1972

Bob Fosse’s adaptation of John Kander and Fred Ebb’s musical takes many liberties with its source material — cutting some characters and songs, adding others, expanding the narrative — but it captures the same sense of mounting doom as the openness and personal liberties of Weimar-era Berlin fade with the rise of fascism. Fosse’s challenges included mounting a musical at a moment when they’d fallen out of favor, and though Cabaret bears little in common with golden age Hollywood musicals, the presence of Liza Minnelli as its star provides a sense of continuity. Anyone expecting a happy ending, however, was in for a shock, and the film’s depiction of ambiguous sexuality and cultural chaos felt just as connected to the ascendant glam-rock movement, which embraced it, as it was to the MGM spectacles of old.

46th Academy Awards: 1973

Film from non-English-speaking countries, however remarkable, usually have to settle for winning in the Best Foreign Language Film category, but every once in a while one breaks through. It’s highly unlikely the Academy would ever have honored Ingmar Bergman’s Cries and Whispers — one of the director’s most grueling films — with a trophy, but doing so would have acknowledged his many contributions to the explosion of European filmmaking talent trying to make sense of what had happened to the world in the years after the Second World War. (Even if The Sting is, admittedly, much more fun.)

47th Academy Awards: 1974

Were it not for the inclusion of Irwin Allen’s dull, star-studded disaster movie The Towering Inferno, this would be a contender for the strongest field of Best Picture nominees ever produced. Bob Fosse’s Lenny and Roman Polanski’s Chinatown remain revered classics, but the year belonged to Francis Ford Coppola, if only because of numbers; Coppola released not one but two Best Picture nominees in 1974. Giving the second slot to another Coppola film might seem excessive, but not only is The Conversation a masterpiece that can stand side by side with The Godfather Part II, it’s a strikingly different film, trading in the epic sweep of his gangster classics for disturbing intimacy in a portrait of a surveillance expert (Gene Hackman) who comes undone when he gets too close to an assignment.

48th Academy Awards: 1975

A magnum opus attempting to do nothing less than capture the downcast spirit of post-Watergate America, Robert Altman’s Nashville follows two dozen characters during a few eventful days in Music City, USA, a place where entertainment and politics intersect and dreamers and cynics rub shoulders. Altman’s habit of carving movies out of hours of heavily improvised footage could easily have gotten away from him — as it sometimes did elsewhere — but the results here are stunning, veering from comedy to tragedy and ending in a kind of fevered madness.

49th Academy Awards: 1976

In 1976, the feel-good picture of the year told the story of a scrappy boxer who rises from obscurity, fights the champ — and loses, securing only a moral victory in the process. Such was the spirit of the times, but Rocky Balboa’s journey looks downright triumphant next to that of Travis Bickle (Robert De Niro), the alienated cabbie for whom New York has become a living hell. Director Martin Scorsese and screenwriter Paul Schrader take the film to the sort of dark places few movies dare to go. The Academy responded with a nomination but no award, but its vision of one disturbed man’s plumbing of the lower depths has proved enduring.

50th Academy Awards: 1977

The ill-defined Outstanding Achievement in Popular Film idea may or may not return in the future. But even if it’s a bad idea, there is some logic to it. Films that capture the public imagination via sensation, action, and special effects tend not to win Best Picture even when they become one of their era’s defining moments. There’s no better example of that than the films of 1977, when Star Wars helped define blockbuster filmmaking, became a pop-culture phenomenon, and took over the imaginations of a whole generation — only to see the top honor go to Woody Allen’s bittersweet story of an on-again, off-again love affair. (Star Wars didn’t exactly fade into obscurity due to the loss, however.)

51st Academy Awards: 1978

Mainstream films mostly stayed away from the topic of the Vietnam War until years after the fall of Saigon, but in 1978, two such films earned Best Picture nominations. Michael Cimino’s The Deer Hunter offered a nightmarish vision of the war, but Hal Ashby’s Coming Home is just as uncompromising in its own way, depicting the homefront experiences of a Marine captain (Bruce Dern), his wife (Jane Fonda), and a paraplegic veteran (Jon Voight) in late-’60s California. The leads and Ashby’s intuitive direction — often paced to the rhythms of hit songs from the ’60s before they became soundtrack clichés — helps capture the spirit of a country still figuring out what it had been through, what it meant, and where it needed to go next.

52nd Academy Awards: 1979

A determinedly small film that’s all the better for its tight focus, this Peter Yates–directed coming-of-age story follows four friends as they try to navigate the strange space between high school and the rest of their lives. The focus belongs to Dave (Dennis Christopher), a talented cyclist infatuated with all things Italian who — with the help of friends played by Dennis Quaid, Daniel Stern, and Jackie Earle Haley — concentrates on participating in a big race and trying to figure out what’s next for him. Filmed and set in Bloomington, Indiana, it keeps a light tone without losing sight of the limited options to the working-class children of the quarry workers who built the college town that now looks down on them.

53rd Academy Awards: 1980

As with the year How Green Was My Valley beat Citizen Kane, Scorsese’s searing Raging Bull loss to Robert Redford’s Ordinary People has become an easy example of how the Oscars often get it wrong. That’s not really fair to Ordinary People, which is a pretty terrific in its own right. But because another Scorsese film got one of our spots above (and will get one below), let’s give this one to The Elephant Man, David Lynch’s retelling of the friendship between John Merrick (John Hurt), a deformed man exhibit in a Victorian freak show, and Frederick Teaves (Anthony Hopkins), a doctor who takes him into his care and helps restore his sense of dignity. A moving costume drama that’s also very much a David Lynch film, it mixes striking black-and-white photography with a compassion for outsiders of all kinds.

54th Academy Awards: 1981

A decades-in-the-making passion project for director and star Warren Beatty, Reds brought the sweep of a Hollywood epic to a subject most epics wouldn’t touch: the life of radical journalist Jack Reed (Beatty), a writer now best known for Ten Days That Shook The World, his account of Russia’s October Revolution. Ambitious at every level, Beatty’s film mixes an all-star cast (one that includes Diane Keaton and Jack Nicholson), stately narrative filmmaking, and documentary interviews with those who knew Reed and his circle. It earned Beatty a Best Director trophy, but the Best Picture prize proved more elusive, perhaps in part because of the film’s refusal to draw any easy conclusions about the radical ideas it depicts.

55th Academy Awards: 1982

A fairy tale set in the American suburbs and dressed up in science-fiction trappings, Steven Spielberg’s E.T. the Extra-Terrestrial suggests that even the most mundane settings could be filled with wonder via the story of an alien who takes refuge with a family still reeling from divorce. For years the highest-grossing movie of all time, its emotionally rich, visually stunning storytelling captures everything Spielberg did better than everyone else at this point in his career. He made it look easy. The many imitators that followed proved that wasn’t the case.

56th Academy Awards: 1983

Adapting Tom Wolfe’s book about the early days of the American space program, Philip Kaufman delivered a movie equal parts epic and irreverent, capturing the danger of spaceflight (and the test-pilot programs that preceded it) and the absurdity of a political environment that pushed it into existence and the media circus surrounding the original astronauts and their wives. In other words, it stays true to the tone cultivated by Wolfe, a movie equally at home depicting awesome achievements and the flawed men and women who made it possible.

57th Academy Awards: 1984

Sally Field’s “You like me!” acceptance speech after she won Best Actress honors for Places in the Heart gave the Oscars a moment sure to be featured in highlight reels from now until the end of the Oscars themselves. Field is remarkable in the film, and it wouldn’t have been a bad Best Picture choice, either. Written and directed by Robert Benton (Kramer vs. Kramer) and beautifully shot by Néstor Almendros, it stars Field as a widow who forms a makeshift family that includes a blind lodger (John Malkovich) and a homeless man (Danny Glover) in a deeply prejudiced Depression-era Texas town. Benton drew from his own memories growing up in Texas, and the mix of affection for and repulsion toward the place that made him can be felt from beginning to end.

58th Academy Awards: 1985

Few directors stayed as engaged and interested in risk from the beginning of their career to the end as John Huston, who kept taking chances until his death in 1985. Prizzi’s Honor, Huston’s penultimate film, became both a critical and popular favorite, but it might have been a disaster without a director as capable of balancing comedy, suspense, and romance, or willing to compromise with a less daring ending — though a cast that includes Jack Nicholson, Kathleen Turner, and Anjelica Huston (John’s daughter) certainly helps, too.

59th Academy Awards: 1986

From the ’60s through the aughts, producer Ismail Merchant, director James Ivory, and screenwriter Ruth Prawer Jhabvala made immaculately sculpted films for art-house audiences, often literary adaptations capturing a way of life now lost to time. Their commercial and critical success found a high-water mark in the ’80s and early ’90s, beginning with this spirited E.M. Forster adaptation starring Helena Bonham Carter, Daniel Day Lewis, Judi Dench, and Maggie Smith. A Room With a View offers stunning Florentine cityscapes, gorgeous costumes, and peerlessly rendered depictions of yearning and repression — essentially everything a Forster adaptation needs and with a cast it’s impossible to imagine improving upon. The team became a kind of lazy shorthand for tastefully unadventurous filmmaking, and unfairly so. Their best films burst with intelligence and passion.

60th Academy Awards: 1987

At once a funny, carefully realized look a complicated relationship and an incisive, prescient study of the power of mass media, James L. Brooks’s Broadcast News is the result both of Brooks’s exhaustive research and the skills with dialogue and character he’d spent years honing via film and TV work. Albert Brooks and Holly Hunter co-star as a journalist and producer, respectively, working in TV news whose aforementioned complicated relationship is shaken up by the arrival of an attractive, inexperienced, charming new reporter (William Hurt) who’s slowly revealed to be a chilling suggestion of journalism’s future.

61st Academy Awards: 1988

Some types of movies that often have a hard time winning Best Picture Oscars, especially in the past few decades: comedies in general, romantic comedies in particular, and most films focused more on women than men. Mike Nichols’s Working Girl, in which Melanie Griffith keeps losing her footing as she climbs the corporate ladder while dealing with sexism and a treacherous boss (Sigourney Weaver), checks all those boxes, making it a dark horse in the year’s race, even if it was one of the most sophisticated and winning comedies of the decade. Playing a character who’s a mix of brains and Staten Island–bred determination, Griffith’s at her most charming here.

62nd Academy Awards: 1989

Oliver Stone would discover there was no cinematic flourish or excessive gesture he didn’t like in the 1990s, but with Born on the Fourth of July, he made one of the best films of 1989, a late entry in a cycle of ’80s movies reckoning with the legacy of the Vietnam War. It’s territory he’d previously explored with the semi-autobiographical (and Oscar-winning) Platoon, but here he uses the experiences of Ron Kovic, a Marine turned antiwar activist who became one of the most prominent voices for veterans after returning home and adjusting to life as a paraplegic. Tom Cruise plays Kovic memorably in a performance that tears down all his movie-star charm, requiring him to be vulnerable onscreen in a way he’d never been before and has rarely been since.

63rd Academy Awards: 1990

Ten years after making one of the best films of his career and losing the Best Picture Oscar to a movie star making his directorial debut, Martin Scorsese did it again. Goodfellas didn’t take the prize but, to put it mildly, it would make a fine alternate choice, having gone on to become one of the most admired — and most imitated — films of the ’90s, a film that captures both the transgressive rush of living outside the law and the long, paranoid comedown of staying in the life too long.

64th Academy Awards: 1991

One of the most beloved products of the Disney animation renaissance that began in the late 1980s — a string of films that breathed new life into both the studio and theatrical animation on the whole — Beauty and the Beast made news as the first animated feature to earn a Best Picture nomination. It would remain the only such film to earn that distinction until 2009, by which time the animated output of Disney, Pixar, and other studios had helped the form shed its reputation as strictly kids’ stuff. Combining classic hand-drawn animation with some computer-assisted flourishes, Beauty and the Beast now looks like a bridge between the past and the future.

65th Academy Awards: 1992

Neil Jordan’s The Crying Game was so defined by its twist that all the other elements that made the film compelling got a bit lost in the conversation. The big reveal is, of course, an unforgettable moment, but it’s just one part of a complex political thriller that begins with a member of the IRA (Stephen Rea) developing a bond with a British soldier (Forest Whitaker) he’s helped to kidnap — a bond that leads him to make good on a promise to look after the soldier’s London girlfriend (Jaye Davidson). It works both as a propulsive suspense film and as an exploration of the slipperiness of identity — national, ideological, sexual, and otherwise.

66th Academy Awards: 1993

The Fugitive almost plays like the result of a dare: What if you made a movie that was basically one long chase scene? Could it work? Could it still feel substantial? Adapting a ’60s TV series that had been a pop-culture sensation in its day, Andrew Davis brought in actors with the gravity to elevate an already smart script, casting Harrison Ford as the wrongly accused man on the run and Tommy Lee Jones as the lawman determined to bring him in. It’s one of the rare action movies to have earned a Best Picture nomination, and it’s not hard to picture it as a winner (at least in a year when Schindler’s List didn’t effectively shut down any competition from the moment of its release).

67th Academy Awards: 1994

Quentin Tarantino (and co-writer Roger Avary) had to settle for the Best Original Screenplay trophy for the era-defining Pulp Fiction. But whether you see Forrest Gump as a sentimental celebration of all things boomer or a sly send-up of the same, Pulp Fiction had more to say about where we were headed as a culture than where we’d been. Which isn’t to say that Pulp Fiction isn’t as rooted in the past in its own way as the Robert Zemeckis–directed winner, but its attempts to get beneath the surface of genre tropes and B-movie thrills through a mix of earnest admiration and irony helped reinvent them for a new generation.

68th Academy Awards: 1995

Winner: Braveheart

Best Loser: Babe

It’s rare that the Academy gets a chance to reward a film and its polar opposite in the same year. The films of 1995, however, offered just such a chance. Instead of going with a story of macho sacrifice and revenge, it could have given the Best Picture honors to Babe, a film that emphasizes the importance of sensitivity, tolerance, and communication via the tale of a pig who doesn’t know he’s not supposed to do the work of a sheepdog so goes ahead and does it anyway. The Academy didn’t, but in our alternative universe, we can.

69th Academy Awards: 1996

“Who are you people?” Billy Crystal quipped in the opening monologue of an Oscars ceremony he dubbed “Sundance by the Sea.” It was a year in which independent filmmaking made itself felt, a trend evident even in the Best Picture category. Of the five nominees, only one, Jerry Maguire, came from a major studio (and even it mostly played like an indie). The award went to the stately The English Patient, arguably the nominee most indebted to classic Hollywood filmmaking. It could just as easily have gone to Joel and Ethan Coen’s Fargo, however, a better representative of what was happening away from the traditional Hollywood system, where the usual rules don’t apply and a film about a pregnant police officer investigating a murder in the upper Midwest could get a green light and find an enthusiastic audience.

70th Academy Awards: 1997

From their labyrinthine plots to their unvarnished — but historically accurate — racial attitudes and language, James Ellroy’s novels have long proven difficult to adapt. Curtis Hanson’s pass at one of his best books cracked the code. It streamlined the plot and turned down the heat on the racism but left the spirit intact, and in Guy Pearce and Russell Crowe — a pair of Australian actors then relatively new to American audiences — it found the perfect embodiment of Ellroy’s morally conflicted protagonists. The result was a fresh take on classic noir themes set in a seedy, bygone L.A. It plays like it was ripped from the pages of one of Ellroy’s books, set in a place where one wrong turn could take anyone down the path to ruin.

71st Academy Awards: 1998

Much like Schindler’s List, everyone knew Saving Private Ryan — an acclaimed film on an important historical topic from a top-tier filmmaker — would win Best Picture from the moment it was released. And then … it just didn’t. Twenty years later, it seems all the odder that a pleasant trifle like Shakespeare in Love — a film released and relentlessly promoted by the Weinstein brothers’ Miramax at the height of its powers — would win out over one of the capstone achievements of Steven Spielberg’s career. But, hey, in our alternate-universe Oscars, that’s easy enough to correct.

72nd Academy Awards: 1999

1999 was a wild year at the movies, yielding one singular film after another, from Three Kings to Fight Club to Magnolia to Being John Malkovich to The Blair Witch Project to The Matrix. Some of these confirmed emerging directors like Spike Jonze and David O. Russell as major talents. Others, like The Matrix, broke new ground with stunning special effects. The year’s Best Picture nominees, however, barely reflected any of this. American Beauty wasn’t exactly a safe choice for the winner, but it was hardly the most inventive offering of the year. Nor were The Cider House Rules or The Green Mile, or even The Insider, a fantastic Michael Mann movie, but one from an established director challenging himself to bring the same sort of tension to a docudrama that he had previously brought to crime films. Of the nominees, The Sixth Sense provided the best indication of what was happening elsewhere in the film world. A seemingly out-of-nowhere supernatural drama crafted with discipline by M. Night Shyamalan, a filmmaker most moviegoers had never heard of, it became a cultural phenomenon by taking viewers by surprise — but the twist never would have worked without the patience Shyamalan invested in the filmmaking or the careful performances by Bruce Willis and Haley Joel Osment.

73rd Academy Awards: 2000

Assuming the Academy sought to reward an action film with lyrical elements as 2000’s Best Picture, they had two easy choices: Ridley Scott’s Gladiator and Ang Lee’s Crouching Tiger, Hidden Dragon. They went with the one that emphasized the action over the lyricism, however. Combat is a form a communication in Lee’s modern riff on the wuxia films of his youth, using stunning fight scenes to tell a story of doomed love starring Chow Yun-fat and Michelle Yeoh.

74th Academy Awards: 2001

Big often wins at the Oscars, and in most years, indies struggle to compete with deep-pocketed studio projects. Despite its critical acclaim and multiple nominations, In the Bedroom never really stood a chance. The first official Sundance selection to earn a Best Picture nomination, the debut film from actor turned director Todd Field is a gutting depiction of violence and its aftermath, watching as the marriage of a happily married couple (played by Tom Wilkinson and Sissy Spacek) fractures after the murder of their son. It’s a small story told with precision, delicacy, and an unflinching commitment to following difficult choices to their unsettling conclusions — all qualities that make it remarkable, even if they may also have hurt its chances to take home any prizes.

75th Academy Awards: 2002

Martin Scorsese would finally win an Oscar a few years later for The Departed, but it would have been just as fitting for him to have won for this story of a rough, long-lost New York starring Leonardo DiCaprio and Daniel Day-Lewis. The film has its problems, particularly toward the end, but its ambition and commitment to recreating 19th-century Manhattan, down to its last muddy detail, mark it as one of the last of the old-style epics, before green screens and CGI made depictions of the past much less tactile and, all too often, much less immersive.

76th Academy Awards: 2003

Any skepticism still lingering about Sofia Coppola after her 1999 debut The Virgin Suicides dissipated with this story of a young woman (Scarlett Johansson) who doesn’t know what to do with herself or her life, and who, left to her own devices in Tokyo, crosses paths with a middle-aged movie star (Bill Murray) in the midst of a midlife crisis. Their relationship keeps shifting the more time they spend together, and the two find an undeniable connection, even if they can’t quite decide what form that connection should take. Coppola’s assured sophomore effort revels in that ambiguity, and in the between-worlds state of its main characters, two people who may never meet again but who come to understand that their chance encounter will reshape how they look at the world for the rest of their lives.

77th Academy Awards: 2004

It’s a credit to how appealing Alexander Payne makes California wine country (and wine itself) look in Sideways that the film provided both the region and its major industry with an economic boost for years after its release — because otherwise it treats its protagonist’s vino obsession as a symptom of a larger problem. A divorced, middle-aged writer, Miles (Paul Giamatti), drinks too much on occasion, but his real problem is the rut into which he’s driven himself, one that no weekend trip to his favorite vineyards with his more successful best friend Jack (Thomas Haden Church) can cure. He’s a mess and he knows it, and his self-loathing ought to make him unbearably unpleasant to watch. But Giamatti’s performance — so prickly and yet so vulnerable — finds Miles’s humanity, and a dim, persistent hopefulness in a film that brought some of the best elements of character-driven ’90s indie films to a wider audience in the succeeding decade.

78th Academy Awards: 2005

We said up front that this would not necessarily be a collection of films that should have won over less deserving winners. But let’s make one exception, because Crash is, well, terrible: a superficial but overheated look at racism that winds up making some pretty pat conclusions. Brokeback Mountain, by contrast, illustrates a different kind of prejudice via a tragic love story, but Ang Lee always puts the film’s characters — movingly played by Jake Gyllenhaal and Heath Ledger — first, focusing on their desires and the disappointments of a world that wants to keep them apart. Even putting aside its value as a breakthrough film that brought a gay love story to mainstream audiences, it’s a deeply felt and beautifully realized film — and its virtues look even more pronounced when it’s placed next to the year’s winner.

79th Academy Awards: 2006

Martin Scorsese finally directed a Best Picture winner (and nabbed a Best Director award) for The Departed, but the Academy could just as easily have given a third trophy to Clint Eastwood for the second of two 2006 films revisiting the Battle of Iwo Jima. Flags of Our Fathers, which recounted the struggle to take a rocky island stronghold from the Japanese in World War II from the American side, is also worthwhile. But its counterpart, which treats the battle from the perspective of the Japanese forces, is even more remarkable, capturing the hellish conditions in which the soldiers fought and the unforgiving ideology that brought them to the battlefield in the first place.

80th Academy Awards: 2007

Do you sometimes have a hard time remembering whether it was No Country for Old Men or There Will Be Blood that won the Oscar for Best Picture in 2007? If so, you’re not alone. Both are tough, violent films anchored by frightening, larger-than-life performances by great actors. And both find darkness at the heart of different chapters of American history. The award went to No Country, a fine choice. But in this alternate universe we’re creating, let’s give it to Paul Thomas Anderson’s film instead.

81st Academy Awards: 2008

Gus Van Sant’s biopic of slain gay rights leader Harvey Milk could easily have fallen into the usual biopic traps, either by trying too hard to show how its subject changed the world or by turning him into a thinly characterized saint. Spearheaded by an empathetic Sean Penn performance, Milk does none of that as it depicts Milk’s immersion in activism, political rise, and murder at the hands of a fellow politician. The film turns an important chapter in American history into a compelling personal story that shows, rather than tells, how one person can make the first ripples leading to sweeping changes.

82nd Academy Awards: 2009

If our Best Picture winners ideally function as a cross-section of what we’ve valued in movies throughout their history, one of the great oversights is that the top honor never went to a Pixar film during that studio’s golden age. Up may not be the best Pixar film, but it’s the best of the two to have earned a Best Picture nomination. (Nothing against the great Toy Story 3, but it’s not even the best Toy Story movie.) The tear-jerking opening segment contains some of the best storytelling the studio has ever created, and the rest is pretty terrific, too (especially if you like talking dogs).

83rd Academy Awards: 2010

It’s a daunting task, attempting to document history while it’s still in progress. Given what’s happened with Facebook and its founder Mark Zuckerberg in the years since 2010, The Social Network might seem to have been premature. But at the turn of the decade, the changes wrought by Facebook were already making themselves felt, and Zuckerberg’s story was already one worth telling. With the strengths of screenwriter Aaron Sorkin and director David Fincher balancing each other out, the film follows Facebook’s evolution from an idea to an unstoppable force and Zuckerberg from his time as a cocky kid with a vision to his adulthood as a mogul adrift in a world he helped create.

84th Academy Awards: 2011

For his magnum opus, The Tree of Life, Terrence Malick set about telling the smallest possible story — the mid-20th-century coming-of-age of a Texas boy who shares some biographical details with Malick — and the largest possible story, leaping from the beginning of time to the afterlife. In the process, the director erases any distinction between the two, letting one life and all its joy and anguish stand in for all of existence. It’s a film of images, moods, and moments more than one of plot, and it expects viewers to fill in the bits of narratives it elides. And although Malick has struggled to recreate the power of this approach in his subsequent films, it’s powerful and affecting here, playing like the film he had spent a lifetime waiting to make, in part out of a need to understand what that lifetime meant.

85th Academy Awards: 2012

Misrepresented in the press before it was even completed and misunderstood after its release, Zero Dark Thirty, Kathryn Bigelow’s sweeping look at the manhunt for Osama bin Laden, as seen through the eyes of Maya, an increasingly obsessive CIA analyst played by Jessica Chastain, works both as a journalistic recounting of recent history and as a consideration of the moral ground surrendered by the U.S. in the years after 9/11. Revenge comes at a terrible price, as is evident in Chastain’s haunted eyes in a quiet final shot that’s as unnerving as any of the preceding action scenes.

86th Academy Awards: 2013

Few directors are as adept at combining technical daring with moving storytelling as Alfonso Cuarón, and with Gravity, he found a project that pushed both of those things to their limits. Stranding Sandra Bullock in space and following her increasingly desperate attempts to find her way home, Gravity is a special-effects triumph meant to be seen on the biggest screen possible (and one of the few post-Avatar films to make meaningful use of 3D). But its power comes just as much from Bullock’s role as a woman struggling to maintain her will to live in the midst of desperate circumstances, and haunted by a profound loss. Cuarón’s images would have been impossible in any previous year, but the film’s themes are timeless.

87th Academy Awards: 2014

Winner: Birdman

Best Loser: Boyhood

Where Alexander Iñárritu’s Birdman (or the Unexpected Virtue of Ignorance) created the illusion of having been shot in a single take, Richard Linklater’s Boyhood played with time in a different fashion. Shot over a period of 12 years, the latter film chronicles the coming-of-age of a Texas kid in a series of well-chosen vignettes. It’s fascinating to watch Linklater attempt to tell a story in a way that had never really been attempted before, meanwhile capturing a changing America in the background. (Dig those iMacs! Remember Harry Potter release parties?) But the film works in large part because Linklater, as usual, lets profundity come to the movie rather than straining to reach it. We see Mason (Ellar Coltrane) go through some rites of passage, but mostly we observe ordinary but telling moments as he gets older and comes into his own. There had never been a film quite like it, and there probably never will be again.

88th Academy Awards: 2015

Tom McCarthy’s Spotlight, a dramatization of the Boston Globe’s Pulitzer–winning investigation into child sex abuse, is a remarkable feat of clear-eyed, efficient, somber filmmaking. George Miller’s Mad Max: Fury Road is in many ways its opposite, a seemingly insane undertaking shot under punishing circumstances and set in a fantastic, speed-crazed, post-apocalyptic world. But Miller’s film — a decades-later installment of a series the director originated in 1979 — is, in its own way, a model of effective storytelling, dropping viewers into a violent, chaotic, resource-starved wasteland and counting on them to catch up as it pits a pair of heroes (Tom Hardy and Charlize Theron) against some cruel overlords. It’s excess with a point, mixing indelible images with powerful emotions.

89th Academy Awards: 2016

The 89th Academy Awards will always be infamous for the mistaken announcement of La La Land — which had been considered a possible, even likely, winner throughout much of the race — as Best Picture. In reality, the award went to the great Moonlight. And though La La Land remains a finely crafted, tunefully entertaining film that doesn’t deserve the backlash it’s attracted, it’s to the Academy’s credit that it went with an unconventional coming-of-age story from an emerging filmmaker that shone a light on corners of the world rarely represented in movies. In a world without Moonlight, however, Kenneth Lonergan’s Manchester by the Sea would also have been a fine choice: a gutting story of loss played with painful intensity — and some well-chosen lighter moments — by a cast led by Casey Affleck.

90th Academy Awards: 2017

Winner: The Shape of Water

Best Loser: Lady Bird

Finally, the 2017 Best Picture nominees suggest another year defined by abundance and variety. The nomination of Guillermo del Toro’s The Shape of Water (which won) and Jordan Peele’s Get Out (a serious contender by most prognosticators’ estimations) signaled that the lines between prestige and genre films had gotten blurrier. Meanwhile, the continued presence of Paul Thomas Anderson and Christopher Nolan in the running confirmed that they remained some of our most reliably ambitious auteurs; their nominations could be seen coming the moment each of their respective films was announced. Not so for our suggested alternative. Greta Gerwig had co-written several previous films and co-directed one, but Lady Bird, her solo debut as a writer and director, still came as a surprise, with its disarmingly personal take on growing up in a certain time and place (Sacramento in the early ‘00s), making an autobiographical coming-of-age story feel at once specific and universal. Gerwig’s film filled the screen with funny, moving performances from the whole cast, but especially from Saoirse Ronan and Laurie Metcalf, as a mother and daughter whose relationship is as fractious as it is loving. Where other nominees went as big as possible, Gerwig proved small could be equally powerful.

91st Academy Awards: 2018

Winner: Green Book

Best Loser: Roma

Sometimes you just know a Best Picture winner is going to turn into a “Wait, what?” As in: “Wait, what? Dances with Wolves beat Goodfellas?” And so forth. Sometimes it just takes seconds for that feeling to kick in. With Green Book, that feeling kicked in almost immediately. “Wait, what? Green Book beat BlacKkKlansman / Black Panther / A Star is Born / The Favourite?” And, more than anything, it applies to Alfonso Cuarón’s deeply personal tribute to not just the times and place that made him but also the live-in maid who helped raise him (played by first-time actress Yalitza Aparicio). It’s a journey through the past not through Cuarón’s eyes but through hers, a one-of-a-kind movie shot in gorgeous black and white that acknowledges the past’s hold on the present and refuses to confine what’s come before nostalgia and misty memories. And it’s that quality that sets it apart Green Book, too, a film too content to think of the past and its divisions as settled business rather than part of an ongoing story. Roma movingly acknowledged that the act of remembering can be as painful as it is revelatory.

92nd Academy Awards: 2019

Winner: Parasite

Best Loser: Once Upon a Time… in Hollywood

Bong Joon Ho’s Parasite winning Best Picture felt shocking for a few reasons. For one, a foreign-language film had never before claimed the top prize, making the honor surprising enough. But it also felt a little off that the Academy would get it so right just one year after getting it so wrong. Most pundits had pegged Sam Mendes’s 1917 as the winner, but the unusually strong movie year of 2019 presented an array of great choices, many of which ended up with nominations. In retrospect, it’s weird how quickly the Best Picture buzz died down around Martin Scorsese’s disarmingly elegiac The Irishman, Greta Gerwig’s daring adaptation of Little Women, and Noah Baumbach’s nuanced divorce drama Marriage Story, all of which might have made strong runs in other years and will certainly be remembered long after awards season ends. So will Quentin Tarantino’s Once Upon a Time … in Hollywood, which finds the director — once an indie interloper, now an industry veteran — re-creating the Los Angeles of his youth and using a story of a friendship, aging, and insecurity to reflect on a moment of tremendous change in film history. The film allowed Tarantino (mostly) to put aside a fixation on revenge narratives that have dominated his 21st-century work in service of a funny, introspective film about the passage of time, the dimming of dreams, and the small triumphs that come from making art within a system that doesn’t always value it — a quality that makes it as much about Hollywood’s present and future as about its past.