Best Picture Oscar Winners of the 21st Century, Ranked

It’s still mind-boggling to think that Paul Haggis’s two-hour lecture about racism (bad), class disparity (also bad), and how we let our many differences divide us when really we’re the same broken people underneath it all (why can’t we all just get along?!?) garnered a half dozen Academy Award nominations, much less won “Hollywood’s highest honor.” We know that the only thing that this industry town’s residents love more than self-flattery is Angeleno-specific self-loathing, yet it still doesn’t quite explain the accolades this ensemble drama received on Oscar night. From the moment that Don Cheadle utters that people miss the human touch “that we crash into each other… just so we can feel something,” you know you’re in for a rough ride. It only gets worse from there, as every character proceeds to speak in bullet points, the symbolism toggles between heavy-handed and butterfingered, and an A-list cast is stuck playing caricatures of corrupt cops, chatty carjackers and cringeworthy Karens. What might have been intended as an attempt to take the nation’s temp during the still volatile post-9/11 era simply read tin-eared and tone-deaf then, and its finger-wagging and phony redemptions feel even more embarrassing now. We have a feeling that were we to revisit this list in the year 2050, Crash would still occupy this same slot.

Another year, another Oscar victory handed to a simplistic, pandering take on our nation’s ongoing race problem solved by the healing power of friendship. Every generation may get the Driving Miss Daisy it deserves, but even the year of American carnage that was 2018 may not have deserved director Peter Farrelly’s based-on-a-true story buddy dramedy. Composer and pianist Dr. Don Shirley (Mahershala Ali, providing the film’s one redeeming factor) hires Anthony “Tony Lip” Vallelonga (Viggo Mortenson) as a driver during a 1962 tour of the Deep South. The two couldn’t be more different personality-wise, but they soon bond during this gamechanging road trip, one man’s lifelong bigotry is miraculously cured, yadda yadda yadda. You can complain about the lopsided perspective of the script cowritten by Anthony’s son Nick Vallelonga, or the way these talented actors keep getting undermined by the clumsy storytelling, or the way in which Shirley’s life as a gay man is treated as a plot convenience when it’s necessary and is ignored when it isn’t. As for the notorious fried-chicken scene, well, words simply fail us here. Somehow, in a mere two hours, you felt as if we’d all taken a half century’s worth of a collective step backward.

There are biopics — that most reliable of Oscar-courting film categories — that want to bludgeon you with tragedy and triumph and an abundance of treacle… and then there is Ron Howard’s drama on the life and times of John Nash, the Nobel prizewinning mathematician who struggled with mental illness throughout his career. It’s not just the way this based-on-a-true-story drama shamelessly works the whole conceit of genius overlapping with madness, whitewashes Nash’s less-than-palatable personal history and qualities to a gleaming alabaster sheen, or blatantly reduces a complicated man into the academic equivalent of a holy fool. It also shoehorns the mighty Russell Crowe, fresh off his Gladiator win, in a role that seems more reverse-engineered to win him back-to-back gold than inhabit a fully dimensional character. We should note that we have no issue with Jennifer Connelly winning for Best Supporting Actress, given how much literal support she’s giving to this ramshackle adaptation of Sylvia Nasar’s biography. Everything else about the movie, however, still throws us into a rage two decades later.

Long before The Crown turned the trials and tribulations of England’s 20th century monarchy into compelling melodrama, there was Tom Hooper’s recreation of the historical moment in which King George VI informed England over the wireless that they are once again at war with Germany. More specifically, it’s about what lead up to that oratorical high point, since His Majesty (Colin Firth) had long contended with a stutter and considered public speaking a fate worse than death. Enter Lionel Logue (Geoffrey Rush), a speech therapist who will privately help King George overcome it with a little bit of moxie and a whole lotta swearing. It’s a combo of a cloying buddy comedy, a sappy heartstring-plucker and the sort of aggressively middlebrow entertainment with a posh accent that once clogged arthouses in bulk. Nothing against Firth, who treats the regent’s stammer-struggle with sensitivity while maintaining a stiff upper lip here, but this is exactly the kind of ingratiating drama that feels reverse-engineered to receive awards over anything else. There’s a word for that, and it rhymes with Schmoscarbait.

The Academy Awards do love a little-film-that-could narrative, which certainly characterizes Sian Heder’s drama about a young woman (Emilia Jones) from a working-class family of fishermen — and who’s also the child of deaf adults — that yearns to break free from her environment and become a world-class singer. It took that year’s virtual festival Sundance by storm, and got snatched up by Apple for a record-breaking $25 million. This textbook example of comfy-chair indie cinema then went on to snag the little gold bald guy, almost in spite of a very tepid FYC campaign on the part of its corporate owners. It was old-fashioned word of mouth, as well as some serious feel-good vibes, that sold this to voters. Not to mention it was a landmark of screen representation for hearing-impaired characters and actors. So why does this Best Picture win still seem so hollow and irritatingly safe? This is the sort of triumph-of-the-underdog film that feels simultaneously uplifting and exhausting, so eager to mount a frontal assault on your heartstrings by any means necessary. It feels formulaic to a fault. We’re still baffled that so many people would apply the adjective “best” to it in any sense of the word.

The year is 1980, the Iran Hostage Crisis has been going on for over two months, and C.I.A. extraction specialist Tony Mendez is at a loss. He’s been tasked with getting six members of the U.S. embassy in Tehran, all of whom avoided capture by hiding out in the Canadian ambassador’s house, out of the country ASAP. Then Mendez hits upon an idea: Pretend they’re a film crew scouting locations, them skirt them back to the States. Now he just needs to convince everyone they’re making a fake movie as a cover. You can see why this stranger-than-fiction story might be catnip for Ben Affleck, who was two films into a promising directorial career (Gone Baby Gone is great, and we like all of the scenes in The Town that don’t involve Affleck filming himself doing pull-ups). This mix of ’70s political thriller and wink-nudge showbiz ribbing never quite comes together, and not even a truly deep bench of great actors — John Goodman, Alan Arkin, Bryan Cranston, Titus Welliver, Kerry Bishé, Kyle Chandler, Victor Garber, Clea DuVall, Scoot McNairy, Philip Baker Hall — can sell lines like, “You’re worried about the Ayatollah? Try the W.G.A.!” Yuk, yuk, yuk. For every dig at the lying, cheating, stealing and backstabbing that characterizes the business we call show, there’s twice as much aren’t-we-grand Hollywood backpatting. Of course voters ate it up!

We like to imagine that someone told Michael Hazanavicius that the moving pictures, “they just don’t make ’em like they used to!” — and then the French writer-director went, Oh snap, let me literally prove you wrong! When this elaborate homage to the adolescent days of cinema premiered at the Cannes Film Festival in the spring of 2011, people politely applauded what felt like a pleasant formalistic experiment. Then a certain Hollywood producer (who shall remain nameless for obvious reasons) got dollar signs in his eyes, and somehow managed to sell an actual black-and-white silent movie to paying crowds and voters. To be fair, both Jean Dujardin and Bérénice Bejo have the kind of mugs perfect for a pre-talkie comedy, and their resurrection of old comic bits and hoofing routines occasionally channels yesteryear’s screen magic. A colleague also pointed out that this film was one spoken “oui” away from being the first foreign-language film to win Best Picture as well. And yet The Artist is still one very twee look backwards that leaves one hell of a saccharine aftertaste, and is the sort of momentarily delightful trifle that manages to skirt out of your memory mere seconds after you’ve seen it. We actually forgot the movie existed, much less won Oscars, until we looked it up for this list.

Clint Eastwood’s clever mix of two tried-and-true staples — the go-the-distance boxing drama and the terminal-illness weepie — had some of us asking the pertinent question: Wait, what year is it again? The actor-director’s old-fashioned blend of Hollywood genres may have substituted a female puglist in the ring (and given Hilary Swank he second best role to date). Yet this felt like a Golden Age flashback in the best possible way, especially given the fact that the filmmaker was old enough to have actually been a studio contract player. The second half doesn’t play nearly as strongly as the first — once the film switches from sports tale to an euthanasia story, the father issues and sentimentality start to bog things down a tad. Still, Eastwood, Swank and his old Unforgiven partner Morgan Freeman know exactly how to keep what should be a creaky, punch-drunk narrative extremely fleet on its feet.

Maybe you’ve forgotten how incredibly popular Who Wants to Be a Millionaire? was in the first few years of the aughts — and why it was likely an easy entry point into Danny Boyle’s Cinderella story about a chaiwallah named Jamal (Dev Patel) who ends up winning big on the Indian version of the game show. His streak arouses the suspicions of a police officer (the late, great Irrfan Khan), who thinks the young man has been cheating; Jamal then recounts how he knew each answer via a life story filled with extreme poverty, anti-Muslim attacks, exploitation, crime, friendship and betrayal. Oh, and there’s also a deep romantic connection with his childhood sweetheart Latika (Freida Pinto). Boyle’s insistence on injecting 10ccs of adrenaline into every set piece and plot twist occasionally becomes exhausting, and the accusations that this adaptation of Vikar Swarup’s novel Q&A was just high-octane cultural tourism weren’t totally unfounded. None of which kept the movie from being a huge critical and box-office hit, or from casting a spell over voters — it walked away with eight Oscars including Best Picture. What stays with you more than the flashy style is Patel’s performance; his breakthrough role already suggests an actor primed for future leading-man status.

Here’s a partial list of the things that Alejandro González Iñárritu’s portrait of an artist in existential free-fall takes issue with: superhero movies, blockbusters in general, Broadway vanity projects, narcissistic New York actors, social media, the media obsession around celebrity, the NY Times, critics, NY Times’ critics, and the painful experience of being a human being both blessed and cursed with an ego. More than any other film on this list, Birdman is arguably the one that’s aged the worst, though you can still so many flashes of brilliance (notably in cinematographer Emmanuel “Chivo” Lubezki’s facility for making it seem as if the film is one continuous shot) in its pretentiousness. In fact, its brilliance and its pretentiousness are actively feeding off each other, locked in conversation in the same way that Michael Keaton’s movie star and his comic-book alter ego are battling it out in his skull. The meta aspect of the man who once played Batman digging into this role remain intact, even if Iñárritu says that was not why he hired him; as for Edward Norton’s preening Method prick, the director admitted that he’s “based on several real people…including Edward Norton.”

Bob Fosse’s raucous Broadway hit about sex, violence, and all that jazz gets an equally razzle-dazzling big-screen adaptation — and the combo of old-timey showmanship, Old Hollywood-style musical numbers and good old-fashioned scenery chewing would prove to be pure catnip for Oscar voters. Renée Zellweger steps into the dance shoes previously filled by the holy trinity of Gwen Verdon, Liza Minnelli and Ann Reinking to play Roxie Hart, a mousy murderer who goes into the clink on a homicide rap and comes out a star. Her rival-turned-partner in crime is Velma Kelly, a role that allowed Catherine Zeta-Jones to rock an excellent Lulu Brooks and win a Best Supporting Actress Oscar, in that order. Coming in hot with 13 nominations and winning six, director Rob Marshall’s movie was the first musical to win Best Picture since Oliver! in 1968. It may be all over the place (we still aren’t sure how we feel about Richard Gere’s take on legal eagle Billy Fish), but the highlights — the showstopping “Cell Block Tango,” still a model of how to use editing, composition and choreography to make a song-and-dance pop; John C. Reilly pathos-driven “Mr. Cellophane” — still slap. And it’s not like the satirical jabs about true crime and celebrity culture have gotten any less punchy.

We’re not going to say that the final entry of Peter Jackson’s trilogy didn’t have a bit of an edge, in that voters really weren’t rewarding just one film — it’s not taking anything away from its win to say that The Return of the King benefited from wrapping up what was, by any stretch of the imagination, a groundbreaking, gamechanging achievement. The Oscar was really going to The Lord of the Rings as a whole rather than one third of it, in other words. Yet that would require the last chapter sticking the landing, which this epic most assuredly does. There’s a glorious full-circle feeling that you get as you say goodbye to these characters (several goodbyes, actually; the dig about the movie having a half dozen climaxes is funny because it’s true), and see the quest to rid Middle Earth of the world’s most tainted piece of jewelry, a.k.a. my preciousssss, finally come to a satisfying conclusion. This was really the movie that sold the idea of modern worldbuilding franchises as an aspirational affair, proving that you could do a big, blockbustery I.P. series that was both prestigious and globally popular. (Remember: Star Wars was in a second-trilogy rut, and The Dark Knight was still five years away.) Even Jackson himself could not repeat the hat trick — let’s forget the Hobbit movies, shall we? — but while this isn’t the “best” of the 21st century Best Pictures, it may be the most prescient about the art form’s future.

In which Guillermo del Toro gives you the gill-boy-meets-girl romance you didn’t know you needed. This Oscar-winner took a premise that might have seemed outrageous on the surface — what if The Creature of the Black Lagoon was actually a consensual love story? — and somehow made it seem like the most tender and totally natural thing in the world. Like so much of the filmmaker’s work, the tale of a mute cleaning lady named Elisa (Sally Hawkins) and the amphibian creature (Doug Jones) who captures her heart seamlessly blends the magical and the macabre even as the film thrusts its anti-conformist commentary front and center. It’s chock full of cinephilia, referencing not just Cold War-era monster movies but also musicals, Hitchcock classics, silent cinema and spy thrillers. But del Toro isn’t aiming to make a wax museum with a pulse here. The movie is all about looking past differences, and though Shape was set in 1962, it hit theaters at a moment in which it appeared that society was on the verge of taking massive steps backward. Add in a pitch-perfect supporting cast (Richard Franklin, Octavia Spencer, Michael Shannon, Michael Stuhlberg) and a production design that’s equal parts drive-in B movie and high-toned fairy tale, and you can see why even stuffy Academy members were won over.

The open road has always been one of American movies’ favorite subjects, but Chloe Zhao’s extraordinary Oscar-winner is more concerned with the endless road — a network of highways, rest stops and campgrounds populated by those who really do think of the journey over the destination. Frances McDormand is Fern, a van-dwelling traveler interacting with actual modern “nomads,” living a life of perpetual motion by choice after everything fell apart. She’s also liberated, something Zhao’s non-judgemental drama goes to great pains to stress; ditto McDormand’s performance, which propels the story even as the director stops to take in the scenery and give the nation’s landscapes plenty of screen time. It was quite an experience to watch someone navigating the wide open countryside while worrying about Covid outbreaks and on-again/off-again lockdowns, which may have played in the film’s favor come voting time. Regardless, it’s a true work of art and a tribute to the gloriously rootless among us.

The very first Best Picture winner of the 21st century was a throwback to a long-retired 20th century movie staple — the sword-and-sandal epic — and damned if Ridley Scott didn’t restore voters’ faith in a genre left for dead. Russell Crowe was at the peak of his Movie Star phase when he played Maximus Meridius, a Roman general who’s betrayed by self-proclaimed new-emperor-in-town Commodus (Joaquin Phoenix, in what feels like an early warm-up for his nutty Napoleon) and ends up fighting in the gladitorial arena. There are bloody showdowns involving spears, battle-axes, chariots and angry tigers, and to answer the rhetorical question Maximus asks: Yes, we were entertained! What’s surprising is how moved we also were by warrior-turned-widower’s quest for vengeance, which has a lot to do with Crowe’s moody matinee-idol performance and Scott’s balance of big spectacle and human-sized drama. Voters likely rewarded it for the nostalgia factor as much as they did for its scale and ambition. Yet it’s aged surprisingly well.

Christopher Nolan cashed in a lot of chips to make this three-hour biopic on J. Robert Oppenheimer, the scientist who helped create the atomic bomb and later found himself hounded by the American government. That alone might have been a hard sell to a studio in the age of superheroes and cinematic universes, but instead of diluting his vision, the writer-director doubled down: There would be chronologically skewed competing timelines, half of it would be shot in black and white, and though he had half of Hollywood in his cast, the lead would be played an Irish actor arguably best known — by American audiences, at least — as the dude from Peaky Blinders. Talk about a gamble that paid off! (And that was before it officially become coronated as one half of the most unlikely cinematic coupling in the history of the movies.) Nolan’s sprawling portrait of the Man Who Would Be Destroyer of Worlds benefits from a depth-charge of a performance by Cillian Murphy and the filmmaker’s determination to go big or go home; it harkens back to the sort of complex, character-driven epics from Reds to The Right Stuff that used to be considered de facto Oscar fodder. Nolan’s grand statement is one of the few modern Best Picture winners that felt like it could have been a 20th century contender as well

Kathryn Bigelow’s stunning ride-along with an Army Explosive Ordinance Disposal in Iraq feels less like a typical “war movie” and more like a wartime procedural, eschewing pro or con Op-Ed viewpoints in favor focusing on the how-to details of defusing I.E.D.s in active combat zones. Just how authentic the film’s depiction of such missions has been debated, yet it remains a nerve-jangling watch, even if you know that the wild-card staff sergeant (Jeremy Renner, in his big pre-Hawkeye breakout role) will make it through a number of near-fatal vignettes. Adrenaline has always been Bigelow’s drug of choice, and her facility for consistently ratcheting the tension up while chronicling both grace and chaos under pressure is what makes the film work. The Hurt Locker will always be a landmark Best Picture win simply for the fact that it became the first movie directed by a female filmmaker to take home the prize. But it’s also the sort of disciplined, go-for-broke type of work that you wished was rewarded by the Academy way more often than not.

Even two decades-plus into a century that’s been nothing if not disruptive, it’s still crazy to think that this gonzo, bonkers film from the duo known as the Daniels actually took home an Oscar — much less the Academy’s big-kahuna prize! Not that their tale of a laundry-owning mother and housewife named Evelyn Wang (take a bow, Michelle Yeoh), who discovers that she’s the only thing standing between the collapse of life, the multiverses and everything, doesn’t deserve every single statuette it took home. It’s simply that, after so many years of the Best Picture awards going to stuffy, stolid and/or totally safe films, the fact that the Academy recognized what a unicorn this anything-goes mix of late ’90s Absurdism, 21st century superhero cinema, martial-arts madness, surreal comedy and Sundance-style character study was speaks volumes. A batshit ride through genres that crossed over into the mainstream and took over the zeitgeist is one thing, but allowing it entry into the same hallowed halls as Chariots of Fire and Gandhi and The English Patient was a welcome step forward. (Bonus points for kicking off Ke Huy Quan’s second showbiz act as well.)

Martin Scorsese switches from Italian-American wise guys in New York to Irish-American gangsters in Boston, and reminds you that it takes more than a slight geographical switch-up to throw him off his Shakespearean crime drama/dark comedy game. There are those who will tell you that this remake of the Hong Kong cops-and-crooks thriller Infernal Affairs was given the gold statuette to make up for the head-scratching Oscar losses our greatest living American filmmaker has suffered over decades (don’t get us started on the whole Goodfellas vs. Dances With Wolves thing). They’re not wrong, exactly. But that theory gives Scorsese’s reimagining of a tale of two deep-cover moles — Leonardo DiCaprio is the cop who’s infiltrated Jack Nicholson’s mob, Matt Damon is leaking precinct news back to his kingpin patron — short shrift. This is a Scorsese picture in every sense, from the film references to the whipcrack energy to the emphasis on betrayal, which has been one of the director’s obsessions from the jump. It also features some of the best work from its two leads, a few crack supporting turns (Ray Winstone! Vera Farmiga!! Mark Fawkin’ Wahlberg!!!) and the last great Jack performance. And the ending is perfect. This won the grand prize on its own merit, people. Act accordingly.

Joel and Ethan Coen took what’s arguably Cormac McCarthy’s weakest novel and turned it into a sunbaked noir, complete with missing cartel loot, a gruff everyman hero, a wizened old lawman, and one of the most memorable psychopaths ever to grace a screen. Javier Bardem’s singularly odd turn as the hit man Anton Chigurh is probably the first thing you think of when you think of this Best Picture winner — his weapon-of-choice cattle gun and that WTF pageboy ‘do are second and third, respectively — yet the brothers’ whipcrack thriller is way more than offbeat haircuts and nihilistic business as usual. It’s a deceptively deep genre film, as much an end-of-empire Western as it is a crime flick; the way that Tommy Lee Jones’ sheriff doubles as a moral conscience or the cynical manner in which criminality is a corporate affair behind the carnage suggests a sun setting on a romanticized version of America’s final frontier. The Coens knew exactly how to goose McCarthy’s gothic prose while still retaining the stark, elegiac poetry of it, and the pairing felt like a match made in heaven even before that last Academy envelope was opened. If this ain’t a deserved win, it’ll do until the real one gets here.