The Oscars are inherently silly. It’s Hollywood giving itself prizes, selecting the best “art” even though art is subjective and it’s impossible to compare two different movies that are each attempting two very different things. And yet the Oscars are also kind of great. They’re a night for celebrating an art form that I love, and they can raise the profile of smaller or more complicated movies that might have flown under the radar for audiences on a steady diet of blockbusters. Not that there’s anything wrong with blockbusters, but oftentimes the films nominated for the Oscars can expand the horizons of those who watch them, and serve as an empathy machine as we experience stories told by a number of different filmmakers from wildly different backgrounds.

The top prize at the Oscars, of course, is Best Picture. Sometimes the Academy does a pretty OK job of selecting the most deserving film, and sometimes they get it really, really, really wrong. Time is the ultimate arbiter of truth, so with the benefit of hindsight, we've gone back and ranked all the Best Picture winners of the 21st century so far – from 2000’s Gladiator up through 2024's Oppenheimer. And for each year, I’ve also selected the film I think should have won. Let’s get started.

24 'Crash' (2005)

Who Should Have Won: 'Brokeback Mountain'

It was really neck-and-neck here for which Best Picture winner took the title for “worst,” as Crash is a film about racism told by a white writer-director who doesn’t do the work to explore or address or solve a darn thing beyond “life is crazy sometimes, right?” Adding to the sting was the fact that the beautiful and poetic Brokeback Mountain was positioned as the frontrunner that year, winning Best Director but losing out on the top prize to a movie that, all these years later, remains one of the most embarrassing footnotes in Oscar history.

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23 'Green Book' (2018)

What Should Have Won: 'Roma'

To be clear, Green Book is not a terrible movie – it’s pleasant, competently made, and Mahershala Ali and Viggo Mortensen give solid performances. But it’s the subtext of the entire piece that really pulls it down, especially in contrast to the other films nominated for Best Picture that year. Green Book is a movie about racism told through the eyes of a white, racist protagonist. Ali’s character literally takes a backseat to the story, which again is about a racist man learning to be a little less racist not because he comes to understand societal problems or has a change of heart, but because a Black man is nice to him. It’s emblematic of larger issues America has been going through for centuries – the notion that empathy for some people only arrives when they personally befriend someone from a prejudiced community. It’s kind of reprehensible, especially when BlacKkKlansman and Black Panther – two great films about race told by Black storytellers and filmmakers – were also nominated for Best Picture the same year.

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22 'Birdman or (The Unexpected Virtue of Ignorance)' (2014)

What Should Have Won: 'Boyhood'

To quote Shakespeare, “Full of sound and fury, signifying nothing.”

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21 'A Beautiful Mind' (2001)

What Should Have Won: 'The Lord of the Rings: The Fellowship of the Ring'

Ron Howard’s true-story account of American mathematician John Nash’s battle with mental illness is a fine movie, and the visual language does a solid job of putting you inside Nash’s mindset, but Best Picture? For A Beautiful Mind? Really and truly the Oscar success of this film felt more like the Academy making up for snubbing Apollo 13, a far superior Ron Howard-directed true story. Legacy-wise, A Beautiful Mind feels more like a bit of trivia than an esteemed Oscar legend, and in hindsight, a deserved win for Fellowship of the Ring would have held up way better.

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20 'Chicago' (2002)

What Should Have Won: 'The Pianist'

Before Chicago, a musical hadn’t won Best Picture since 1968’s Oliver!, and while a musical hasn’t won since, the impact of bringing theatrical experiences to the movies remains a big draw, thanks to Rob Marshall’s adaptation. Chicago flaunts its musical numbers with flashy pizazz in a style that would’ve made Bob Fosse proud—coincidentally, Fosse originally wanted to direct a film version but died before he could.

While Marshall’s subsequent musicals would often struggle to mix its songs with a narrative, Chicago makes the songs the true star, as performed by a cast that included Renée Zellweger, Richard Gere, Queen Latifah, a heartbreaking John C. Reilly, and an Oscar-winning Catherine Zeta-Jones. Chicago blended an old-school musical with a 1920s murder story to create a film that brought back the big-screen musical in a major way.

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19 'Slumdog Millionaire' (2008)

What Should Have Won: 'Milk'

2008 was a really strange Best Picture lineup. You had Fincher’s ambitious yet not quite great The Curious Case of Benjamin Button, Ron Howard’s talky Frost/Nixon, Gus Van Sant’s sensitive biopic Milk, the eventual winner Slumdog Millionaire, and then, of course, the sensation that everyone was talking about…The Reader. That last one sneaked in there instead of The Dark Knight and is directly responsible for the expanded Best Picture category. But looking back, Slumdog Millionaire holds up pretty well. It’s a fairy tale of sorts, but the kineticism with which Danny Boyle captures the story sets it apart, and boy oh boy is it a crowd-pleaser. Is it one of the greats? Not really. But certainly not one of the worst.

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18 'The Artist' (2011)

What Should Have Won: 'The Tree of Life'

The bottom of this list really is made up of Oscar Movies That Time Forgot, but The Artist is unique in that this movie nearly ran the table. It won Best Picture, Director, and Actor, and then almost immediately disappeared. The love letter to the silent film era is a fascinating experiment of sorts, and it’s well-crafted. It’s just the kind of movie you see once, think was pretty fun, and then immediately forget about. Meanwhile, Terrence Malick is over here pondering the meaning of existence and he gets zilch.

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17 'CODA' (2021)

Who Should Have Won: 'The Power of the Dog'

CODA, from writer/director Sian Heder and based on the French-Belgian film La Famille Bélier, is an incredibly earnest and big-hearted film about Ruby (Emilia Jones), the only hearing member of her deaf family, as she attempts to find her own identity away from them. While many proclaimed CODA was the type of feelgood film that the Oscars of course are going to gravitate to, I suggest you look at the rest of this list and tell me where those other feelgood films are exactly? CODA is the type of tender, good-natured film that we certainly don't get enough of in this category, and while it might not stand the test of time in the way that The Power of the Dog or West Side Story might, it's a nice change of pace for this award to try a little kindness and warmth.

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16 'The King’s Speech' (2010)

What Should Have Won: 'The Social Network'

The King’s Speech is arguably one of the best examples of a Best Picture winner whose legacy would be far greater had it never won this honor. Winning in one of the strongest years in memory against films like Black Swan, Inception, The Social Network, and Toy Story 3, The King’s Speech has unfortunately been defined by what it beat rather than on its own merits.

Tom Hooper’s regal drama is actually quite a bit of fun and easily the director’s best work, focusing on the relationship between the stuttering King George VI (Colin Firth) and his speech therapist, Lionel Logue (Geoffrey Rush). Firth and Rush are delightful together, and Hooper shoots this story with unique, unconventional framing to make it look a bit more dynamic than the standard biopic. But in a film full of some big choices, Helena Bonham Carter, as Queen Elizabeth, is doing some beautifully subtle work, speaking multitudes with just a tear-filled glance. The King’s Speech wasn’t the best film of 2010, but that shouldn’t take away from an immensely enjoyable historical drama.

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15 'Million Dollar Baby' (2004)

What Should Have Won: 'Sideways'

The 2000s might’ve been the last exceptional decade for Clint Eastwood as a director, finding his own angles on stories seen time and time again, whether in the murder mystery of Mystic River or acknowledging both sides of World War II with Flags of Our Fathers and Letters from Iwo Jima. But Million Dollar Baby became the pinnacle of this period, a film about a boxing trainer, Frankie (Eastwood), a hopeful boxer, Maggie (Hilary Swank, earning her second Oscar), and Frankie’s employee and friend, Eddie (Morgan Freeman, somehow winning his only Oscar).

Working with a screenplay by Paul Haggis, Eastwood focused more on the found family of this trio and the painful pasts that they’d much rather leave behind, making this far more than just a typical boxing film. While Million DollarBaby rightfully received criticism for its ending, Eastwood mostly managed to show that he was still a director at the top of his game, even in his 70s.

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14 'Argo' (2012)

What Should Have Won: 'Lincoln'

Argo truly couldn’t care less that it’s a movie about Hollywood helping save American hostages in Iran or that the facts are clearly altered to make for a better story. All Argo, the third film directed by Ben Affleck, truly cares about is making a satisfying popcorn film with a stupendous cast that leaves viewers on the edge of their seats—and in that, Argo succeeds. In fact, the way Affleck builds the tension, especially in the film’s third act, is so strong that it’s hard not to be a bit peeved that Affleck was snubbed in the Best Director category. Affleck’s crowdpleaser feels like a film from an era of Hollywood long passed, the kind of film that makes audiences want to clap in the theater when the good guys save the day. Just a few years earlier, Affleck was sort of brushed off as a joke, but by getting behind the camera and making the trifecta of Gone Baby Gone, The Town, and Argo, Affleck proved that he was the real deal.

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13 'The Shape of Water' (2017)

What Should Have Won: 'Get Out'

Right up through Oscar night, it seemed kind of wild that The Shape of Water was the Best Picture frontrunner. Not because it’s a bad movie, mind you – Guillermo del Toro’s fantastical ode to outsiders is a lovely and beautiful and tremendous achievement. But because it seemed wild to think the Academy would give its top prize to a movie about a Fish Man falling in love with a human woman. And yet here we are, and what a fantastic sight it was to see del Toro taking the stage and accepting the trophy for this genuine labor of love. 2017 was a great year overall for Best Picture, and a win for the aching love story Call Me by Your Name or the brilliant Get Out would have been A-OK as well. At least Three Billboards didn’t win, right?

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12 'Gladiator' (2000)

What Should Have Won: 'Traffic'

Once upon a time, Hollywood used to make big, grand period pieces that were expensive and dramatic and compelling, and weren’t packed with visual effects or aliens or creatures. Gladiator is the last Best Picture winner in that vein, and Ridley Scott’s stylized sword-and-sandals movie holds up probably better than you remember. Its story feels huge and personal all at once, and Russell Crowe gives a towering lead performance. A case could be made that Steven Soderbergh’s brilliant War on Drugs drama Traffic deserved Best Picture instead (Soderbergh won Best Director over Scott), but there’s something about Gladiator that feels truly unique. Like Scott pulled a fast one and got away with something.

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11 'Everything Everywhere All at Once' (2022)

Who Should Have Won: 'Everything Everywhere All at Once'

Everything Everywhere All at Once is easily the weirdest film to ever win Best Picture in its almost century-long history. Who could've imagined back in 1927 at the first ceremony that Best Picture would go to a film featuring hot dog fingers and fights involving buttplugs? But Daniels' second film is more than just its weirdness, it's a remarkably ambitious film about family and the paths that we choose as opposed to the ones that we didn't. Everything Everywhere deserved every one of its seven Oscar wins, including Best Director, Best Writing, and a record-tying number of acting awards for a single film. Everything Everywhere All at Once proved that weird films could have incredible showings on Hollywood's biggest stage.

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10 'The Hurt Locker' (2009)

What Should Have Won: 'Inglorious Basterds'

It was a battle between David and Goliath in 2009 as James Cameron’s massively expensive Avatar squared off against the little-seen indie The Hurt Locker, but the better movie came away the victor. Kathryn Bigelow’s film gets at the psychological toll that war takes on the humans fighting in it, and the movie pulls no punches as it traces a bomb disposal expert both inside and outside of the Iraq War. And yet, as great as The Hurt Locker is, as time has gone on it has become clear that Inglourious Basterds is truly Quentin Tarantino’s masterpiece.

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9 'Spotlight' (2015)

What Should Have Won: 'Mad Max: Fury Road'

Spotlight is one of the more unlikely winners of the 21st century, but it exemplifies an important and difficult story told efficiently and well. It’s not showy or flashy, but the way Tom McCarthy assembles this journalism story is just right. And yet it’s a testament to the strength of the nominees that year that you could have picked a number of winners and it would have felt fine. The correct choice, however, must be Mad Max: Fury Road. An action masterpiece unlike anything we’d seen before, or likely anything we’ll see since.

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8 'Nomadland' (2020)

What Should Have Won: 'Nomadland'

2020's Best Picture winner is also one of the most intimate winners of all time, as Chloe Zhao’s naturalistic, docudrama approach to Nomadland provides a deeply felt path toward empathy for the film’s characters. This is a movie about those who society has cast aside – the people the world tends to forget about. It not only puts a spotlight on them, but also digs deep to understand them. There’s an undercurrent of pain and heartache running through almost every character in Nomadland, and yet there’s also a beauty to the way they live and the way they look at the world. This is a film about humanity.

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7 'The Departed' (2006)

What Should Have Won: 'The Departed'

While we can certainly argue that Martin Scorsese deserved the Best Picture/Director combo at least two other times in the past, for better movies perhaps, The Departed is far from a bad or even average film in the director’s filmography. This crime thriller is sprawling in its scope, yet never loses sight of the characters at its center. The dichotomy between Leonardo DiCaprio’s undercover cop and Matt Damon’s undercover criminal is cleverly drawn, and DiCaprio gives a nuanced performance as a man who’s spent so much of his life pretending that he’s not even really sure who he is. But perhaps Scorsese’s greatest achievement with The Departed is that the film is just phenomenally entertaining. This is a popcorn movie by way of one of cinema’s greatest auteurs.

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6 'Oppenheimer' (2023)

What Should Have Won: 'Oppenheimer'

Christopher Nolan has been one of the most exciting filmmakers of the 21st century. He's played with time and story structure in nearly every film, showing a darker side of Batman and traveling inside the mind and to the outer reaches of space. But one of the most fascinating things about Oppenheimer is how much growth it shows from Nolan as a filmmaker, as he's using techniques long associated with him, but in a way that shows maturity and evolution in his filmmaking.

Nolan is known for grand, complex, and expansive concepts, but with Oppenheimer—led by a quiet, magnificent performance by Cillian Murphy—Nolan captures his trademark grandiosity into the story of one insular man, presenting the same massive impact his other films have had, and with an emotional, staggering core unlike we've ever seen in his work. By focusing on one of the most important men of the 20th century, Nolan crafts one of his biggest films yet, and everything from its absurdly huge cast, the intense score by Ludwig Göransson, the dynamic editing, and, of course, Nolan's brilliant directing and screenplay, might make this his best and most mature film yet.

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5 '12 Years a Slave' (2013)

What Should Have Won: '12 Years a Slave'

There’s a view of the Oscars as routinely recognizing “the most serious dramas,” with films that touch on specific subjects like slavery serving as “Oscar bait.” And while that could be true of some films for sure, that reputation does a disservice to the brilliance of Steve McQueen’s stark and affecting and brilliant 12 Years a Slave. The filmmaker known for long steady takes and meticulous, human-centric storytelling captures the life of a slave in the American South in emotionally devastating fashion. The film never comes off as cloying or manipulative because McQueen knows he doesn’t need to push for “emotional” moments. By simply portraying the events as they actually were and maintaining an intimacy with the cinematography (shout out to Sean Bobbitt), 12 Years a Slave lays bare one of humanity’s greatest sins and asks us to witness what so many want to forget.

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