Best Picture Oscar Winners of the 21st Century, Ranked

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 2025's One Battle After Another. And for each year, I’ve also selected the film I think should have won. Let’s get started.

26 '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. At least Roger Ebert loved it.

25 '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 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.

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

What Should Have Won: 'Boyhood'

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

23 '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 win for The Fellowship of the Ring would have held up way better.

22 'Chicago' (2002)

What Should Have Won: 'The Pianist'

Before Chicago, a musical hadn’t won Best Picture since 1968’s Oliver! A musical hasn’t won since, but 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 their 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.

21 'Slumdog Millionaire' (2008)

What Should Have Won: 'Milk'

2008 had 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.

20 '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 it nearly ran the table. It won Best Picture, Director, and Actor, and then almost immediately disappeared. The heartfelt love letter to the Silent 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.

19 '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 identity away from them. While many proclaimed CODA was the type of feel-good 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 feel-good 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.

18 'The King’s Speech' (2010)

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 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.

17 '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 new 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 in his only Oscar-winning performance).

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 Dollar Baby 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.