The 21st century is less than two decades old, but its first batch of Best Picture winners already paint an extraordinary portrait of a world in flux.

From a massive historical epic to an intimate digital indies — from a musical that riffs on showbiz standards to period drama that reflects on present crises — these 17 films range from “problematic” to “perfect” and hit all points in between.

More than that, they illustrate Hollywood’s evolving definition of greatness, and the relationship between the film industry and the times that forge it.

Here are the 17 Best Picture winners of the 21st century, ranked from worst to best:

17. Crash (2005)

The director of the film Paul Haggis has said his movie didn't deserve an Oscar IMDb

Brokeback Mountain deserved better, but the Academy didn’t know it. Paul Haggis’ painfully obvious ensemble drama about racial prejudices in Los Angeles was a smug, one-note drama designed to make white liberals feel good about themselves. (It took a decade for Get Out to put this recurring tendency in its place.) The spin-the-racial-wheel structure careens from a black filmmaker to a Persian immigrant to a Hispanic locksmith as it heads toward a tidy climax in which everyone’s bias comes to a head.

The movie was released early in the year and gradually crept back into the conversation so the Academy’s homophobic contingency had a backup plan as Brokeback gained momentum. But perhaps that’s unfair: Some very reasonable people like Crash, which is so sincere and eager to make its purpose obvious that support for the movie was synonymous with endorsing its good intentions. It’s possible to appreciate the outlook of Crash while still recognising that it’s a bad movie; unfortunately, Oscar season circa 2005 wasn’t interested in subtle distinctions. — Eric Kohn

16. The King’s Speech (2010)

Tom Hooper’s snoozy character study about the stuttering future King George VI’s attempt to get over his impediment and deliver a declaration of war on Germany demonstrates the worst tendencies of Oscar bait: weighty subject matter given a quirky, entertaining twist. That was the Weinstein formula in a nutshell.

Colin Firth does his thing in the lead, carrying this gimmicky period piece along as well as possible, but The King’s Speech never manages to wrestle free of its obvious framework. At this point, as best picture winners go, it speaks to another era — when the most boring, unadventurous option is automatically the consensus choice. — EK

15. Argo (2012)

It’s crazy to think that, only five years ago, Hollywood awarded their highest honour to a glorified TV movie because they felt bad for Ben Affleck. And the only reason they felt bad for Ben Affleck was because they forgot to nominate him for their highest individual honour. Oscar narratives sure take on a life of their own. Of course, as is often the case, Argo doesn’t fully deserve the scorn it continues to receive for being an undeserving Best Picture winner; it’s a fine little historical thriller, smartly crafted and suspenseful from start to finish.

There’s not much to it beyond the fun of watching the guy from Good Will Hunting sneak a bunch of Americans out of Iran during the Revolution, but that is fun. Affleck knows how to put a good story together, and it’s hard to regret sitting through anything that stars Bryan Cranston, John Goodman, Kerry Bishé, Victor Garber, Richard Kind, and/or Clea DuVall. Still… it’s never a great sign when a movie gives the impression that it directed itself. —David Ehrlich

14. Chicago (2002)

Hardly the worst of the Hollywood musicals that have plagued the screen since the turn of the century, Rob Marshall’s feature debut is a rather modest little movie for something that precipitated monstrosities on the magnitude of Les Misérables, Phantom of the Opera, and Rock of Ages. All razzle dazzle and no real substance, Chicago essentially just offers you a front-row seat at a Broadway theatre; Marshall blindly embraces the cabaret vibe of Fosse’s original show, directing the adaptation like someone who got to reach for the stars but only knew how to shoot for the stage.

Every exterior sequence just feels like a glorified set change, and any attempts to gussy up the story ultimately reveal how thin it was in the first place. Still, Renée Zellweger is a phenomenal Roxie Hart (The Press Conference Rag is a highlight), and Richard Gere is a delightfully slimy Billy Flynn. Fun fact: Not a single human being has actually watched this film since 2003. — DE

13. A Beautiful Mind (2001)

The film was inspire by the best-selling Pulitzer Prise nominated book of the same name IMDb

Ron Howard’s story of brilliant economist John Nash (Russell Crowe), whose astonishing ability to decipher Soviet code for the Pentagon is upended by his bouts of paranoid schizophrenia was a major best picture contender even before the cameras started rolling. Howard’s involving direction, guided along by Akiva Goldman’s screenplay, gives Crowe a role ideally suited to his dazed expression — an ideas man perpetually lost in thought.

None of that makes A Beautiful Mind a great movie, but in the pantheon of obvious Oscar bait, it’s one of the least offensive entries, a sturdy biopic that overextends its self-importance but more or less hits its emotional beats on cue. — EK

12. The Artist (2011)

One hundred minutes of empty throwback charm, The Artist was a lovely and innocuous little movie before Harvey Weinstein got his dirty hands on it and made the low-budget French comedy into an Oscar-winning punchline. When Michel Hazanavicius’ cute homage to silent cinema first premiered in competition at Cannes, it was rightfully seen as a crowd-pleasing bit of fluff in a lineup defined by portentous masterpieces like House of Tolerance and Melancholia.

By the time it swept to the stage of the Kodak Theatre the following year, this peppy riff on Singin’ in the Rain had become regarded as the kind of milquetoast, masturbatory nonsense that can turn an awards season into an endless slog. Don’t blame star Jean Dujardin for that, who does a wonderful job of channelling Gene Kelly, or Berénice Bejo, a delightful ingenue who shines as a delightful ingenue; some of their scenes together are almost worthy of Stanley Donen. And don’t you dare blame Uggie, whose tell-all memoir reveals the full depth of his performance. This is just show business. — DE

11. Slumdog Millionaire (2008)

Is Slumdog Millionaire the weirdest movie to ever win Best Picture? Its triumph at the Oscars seems almost as unlikely as Jamal Malik’s on Who Wants to Be a Millionaire?, and that show was literally rigged against him (why Sony Television ever agreed to let one of their flagship programs get besmirched like that is still a mystery). How could a poor Chaiwala from a Juhu slum become rich overnight and then perform an infectiously choreographed dance with the beautiful love of his life!? Such is the power of cinema.

Danny Boyle’s Indian fairy tale won people over with its propulsive energy, revising classic Bollywood tropes for international audiences through a rags-to-riches story about the value of dreams (or is it destiny?) in an economy that’s fixed against you. None of it is very nuanced, and all of it is very Danny Boyle, but the colourful and vividly emotional tale caught on with even casual moviegoers, which might be the film’s greatest homage to the Hindi blockbusters that inspired it. — DE

10. Birdman (or the Unexpected Virtue of Ignorance) (2014)

Boyhood was robbed, considering that Richard Linklater pushed the boundaries of filmmaking by telling a story over 12 years, while Alejandro G. Iñarritu made a fast, fun look at artistic vanity in the face of commercial exhaustion. Still, at least the winner had plenty going on. On the face of it, Birdman is a ridiculous exercise in style, an obvious, over-the-top bid to make Michael Keaton relevant again, but that’s also part of its meta charm.

The swirling camerawork and staccato rhythms of the soundtrack put viewers firmly within the confines of Keaton’s head, and it’s one of the most energetic insights into the rough-and-tumble nature of showbiz since All That Jazz. Hollywood likes to salute its own legacy, but Birdman turns it inside out; in retrospect, its best picture win may have been the turning point that set the stage for more unorthodox Oscar contenders. — EK

9. Million Dollar Baby (2004)

A lean, mean, welterweight of a movie that ends with a punch to the gut and leaves a more lasting bruise than anything Clint Eastwood has made since, Million Dollar Baby is an old-fashioned melodrama in the guise of a sombre — but relatively standard — boxing drama. Eastwood’s on-screen presence helps give the film some extra gravitas, while Hilary Swank delivers a memorably feisty performance as a natural fighter whose ambition gets the better of her. The chemistry between the two leads is clear and immediate, and a half-blind Morgan Freeman shows up to help ease even the most stubborn members of the Academy into the film’s comfortable rhythms.

And then, just when you think you’ve got a handle on things, Eastwood socks you by revealing that this nice underdog story is actually a stone-cold morality play about the American Dream and how quickly it can have to be deferred. Paul Haggis’ screenplay is solid but characteristically schematic, but Eastwood’s blue-collar direction helps keep things real… at least until the third act, when a handful of cartoonish new characters tip upset the balance and leave the film feeling like less of a knockout than a split decision. —DE

8. Gladiator (2000)

The blockbuster grossed over £300 million worldwide IMDb

Are you not entertained!? These days, it’s unlikely that a major studio would even agree to make an original spectacle like Gladiator, as the Academy Awards are dominated by indies that have a greater appeal to voters than they do to the population at large. But back in the halcyon days of 2000, right before the digital revolution came along and changed the game, historical epics still fit into the Oscars as naturally as a cigar fits in Ridley Scott’s mouth. And so we got Gladiator, a muscular, somewhat rousing dad movie that benefited from a plot so simple Joaquin Phoenix could sum it up in just three sentences: “The general who became a slave. The slave who became a gladiator. The gladiator who defied an emperor.”

More memorable for its full-throated yelling than it is for its storytelling, Scott’s film is the brawny sort of entertainment that Hollywood used to believe themselves capable of making. It’s not particularly moving, and its sinister influence on shaky-cam action scenes is not to be overlooked, but the movie did make Russell Crowe fight a tiger, and for that we should always be grateful. — DE

7. Spotlight (2015)

In Birdman, Michael Keaton delivered on the rare challenge of a role that actually called for overstatement. That attribute is nowhere to be found in Tom McCarthy’s Spotlight, in which Keaton heads up a robust ensemble cast as the morally conflicted leader of a Boston Globe reporting team. An intelligently paced portrait of the muckraking 2001 efforts that led to countless revelations of sexual abuse in the Catholic Church, the tone of Spotlight echoes Keaton’s nuanced turn.

As much as Spotlight salutes journalistic achievements, it works best when probing its shortcomings. There’s no finer barometer for studying this struggle than Keaton’s performance, which embodies the internal process of trying to do the right thing — and instead achieving the opposite effect. Its Best Picture win somehow feels even more timely now than it did in the spring of 2016. — EK

6. The Hurt Locker (2008)

The first entry in the most exciting period of Kathryn Bigelow’s career finds her transforming the experiences of a bomb detonation unit in Iraq into a remarkable feat of suspenseful filmmaking. Bigelow broke the Academy’s glass ceiling by becoming the first (and so far only) woman to win an Oscar for best directing, but no one could argue that a progressive agenda pushed her to the top more than the sheer brilliance of her achievement here, as she takes the familiar circumstances of straight-faced men risky their lives in dreary, dusty landscapes and make that risk into a deeply visceral experience.

The gut-punch of the finale suggests that for a select few in the heat of the action, the intensity of risking one’s life for dubious reasons is addictive. It’s an astonishing slow-burn thriller with real ideas, and Mark Boal’s journalistic screenplay gives each scene an undercurrent of realism that cuts deep. — EK

5. The Departed (2006)

One day, hopefully not that far off from now, historians will reflect on the cinema of the early 21st century and recognise that it was a golden age for Martin Scorsese. Maybe — hold on to your hats — the golden age. Galvanizing the director’s flirtation with Leonardo DiCaprio into a beautiful partnership, The Departed is a textbook example of how to (and why to) remake a foreign hit from a Western point of view. Scorsese leverages Andrew Lau and Alan Mak’s Infernal Affairs into a knotted Boston crime saga that bristles with local flavour and a uniquely American sense of loneliness.

The Departed riffs on Scorsese’s earlier gangland classics without infringing on them, DiCaprio’s fevered performance becoming a perfect foil for Matt Damon’s natural smarminess and helping to give the movie a feeling all its own. And if that long-rumoured Toni Erdmann remake never happens, at least this endlessly re-watchable epic gave us one last great showcase for what made Jack Nicholson special. — DE

4. 12 Years a Slave (2014)

Steve McQueen’s measured portrait of northerner Solomon Northup’s tumultuous experience being kidnapped into slavery was Oscar bait before it even existed, so it’s a small miracle that the result is so much more than that: a gorgeous, lived-in world that acknowledges the realities of slavery in extraordinary detail, reckoning with a dark chapter in American history while taking none of it for granted.

Chiwetel Ejiofor was robbed of a best actor win, and McQueen was the unlucky auteur who had to go toe-to-toe with the director of Gravity. Thankfully, he still got his moment to bask on the stage anyway, celebrating a poetic accomplishment that communes with the past while giving it renewed immediacy. — EK

3. The Lord of the Rings: The Return of the King (2003)

The movie blockbuster is the highest grossing film by New Line Cinema IMDb

No movie has ever won more Oscars than The Return of the King, and yet the climactic chapter of Peter Jackson’s (first) trilogy still feels insufficiently appreciated. For one thing, it’s a 203-minute epic that feels like it goes by for only a fraction of its length, Jackson turning one of the most familiar novels in the English language into a fresh and immediate heart-in-your-throat adventure on par with the best of David Lean.

Yes, the film’s victory was obviously in honour of the franchise as a whole. And yes, that epilogue does have quite a few parts to it. But The Return of the King also stands on its own two (hairy) feet, gracefully mining the rich veins of emotion that Jackson has laced throughout the previous two episodes. Also, each of the film’s many different endings packs a solid punch, and the slow-motion sincerity of those final moments somehow makes you feel as though 10 hours of bittersweet beauty are welling up all at once. And not for nothing, but, that Annie Lennox song over the closing credits is a banger for the ages. — DE

2. No Country for Old Men (2007)

As enduringly relevant as anything the Coen brothers have ever made, No Country for Old Men is a breathlessly tense cat-and-mouse drama about a simple Texas guy trying to survive a world that has no mercy for him or anyone else in it — a place that’s already dim and growing darker by the day. Starting with Cormac McCarthy’s novel of the same name and then vacuum-sealing it shut with terse direction that prioritises the threat of death above all else, the Coen brothers created a movie that absolutely drips with existential dread.

Even when Anton Chigurh casts a long shadow even when he isn’t on screen, his violent memory sticking to our bones like a winter chill. No Country for Old Men may not have been such a surprising Best Picture winner in the immediate aftermath of The Departed, but it’s always something of a shock when the Academy anoints anything this good. — DE

1. Moonlight (2016)

Of course the greatest cinematic accomplishment to nab best picture this side of 2000 would barely make it to the finish line, finding its way to the stage only in the clumsiest, most roundabout fashion in history. Barry Jenkins’ intimate, expressionistic queer drama channels some of the finest impulses of international filmmaking into a refreshing new context — a landmark achievement in black cinema and a gorgeous, intimate statement on the desire for companionship in an alienating world, Moonlight both speaks to an underserved audience and raises the bar for the art form by forging an entirely new aesthetic of isolation.

One of the greatest love stories ever told might sound like Oscar bait, but no Oscar bait ever looked quite like this. Whatever happened onstage when Faye Dunaway mistakenly read La La Land, the error registered as an illustration of just how hard it is for daring, unconventional art to make its way into the centre of Hollywood glitz. La La Land is fine, but thank god she had it wrong. — EK