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 from 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 I’ve gone back and ranked all the Best Picture winners of the 21st century so far – from 2000’s Gladiator up through 2021’s Nomadland. And for each year, I’ve also selected the film I think should have won. Let’s get started.

RELATED: Every Best Actor Winner of the 21st Century Ranked From Worst to Best

What 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 that 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.

What Should Have Won: A Star Is Born

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.

Really and truly, the problems with Green Book – again, a movie about racism – can be summed up by the image of the almost entirely white producers and filmmakers taking the stage to accept the award at the end of the night.

What Should Have Won: Boyhood

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

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.

What Should Have Won: The Aviator

Here’s another pretty fine movie that has almost entirely faded from memory. Once upon a time Clint Eastwood was an Oscar darling, and a year after his drama Mystic River was heavily lauded, Million Dollar Baby was the big winner, taking home a number of prizes including Best Picture. It’s a fine sports drama, and Hilary Swank certainly earned that Oscar. But Martin Scorsese’s fairly radical approach to visualizing The Aviator probably holds up better, although it’s also OK to admit this was a pretty weak Best Picture year overall (Remember Ray? Anyone?)

What Should Have Won: The Social Network

Listen, I have written ad nauseam about how mad this particular Oscar year makes me. The King’s Speech is not a terrible movie. It’s fine. It’s inspiring, I suppose. But The Social Network is, quite frankly, one of the best films ever made. It and David Fincher both 1000% deserved Oscars this year, and it’s a crime that they were beaten out by such a middling drama. I mean truly, how does Tom Hooper win Best Director over Fincher this year? How? HOW? Ugh. There I go, getting all worked up again.

RELATED: ‘The Social Network’ Should’ve Won Best Picture and I’m Still Mad About It

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.

What Should Have Won: Slumdog Millionaire

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 in lieu 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.

What Should Have Won: Lincoln

Argo is kind of the solid, agreeable Best Picture winner that’s hard to get mad at. Ben Affleck’s political thriller is sleek and compelling yet also charming and funny, as it has one foot in the madness of Hollywood and the other foot in the complicated socio-political atmosphere of the 1970s. Many chalk its win up to the Academy as a whole rebelling against the Director’s Branch’s decision to snub Affleck (who straight-up won the DGA award that year) and they could be right. The competition was fierce, from Kathryn Bigelow’s controversy-riddled Zero Dark Thirty to the “feel-good” nominee Silver Linings Playbook, but looking back I think Steven Spielberg’s Lincoln deserved it. Far more than just a biopic of a Great Man, Lincoln ponders what America really is, and what our legacy as a country should be.

What Should Have Won: Gladiator

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.

RELATED: Connie Nielsen Explains Why Working With Joaquin Phoenix and Russell Crowe on ‘Gladiator’ Was an Unpredictable Gift

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.

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.

What Should Have Won: Call Me by Your Name

Right up through Oscar night, it seemed kind of insane 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?

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.

What Should Have Won: Nomadland

The most recent 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 towards 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.

What Should Have Won: Chicago

Chicago is one of the best movie musicals ever made, and despite the Academy’s bias against this particular genre over the last few decades, they saw fit to acknowledge this pretty towering achievement. The genius of director Rob Marshall’s adaptation was the choice to showcase the musical numbers as occurring inside Roxy’s (Renee Zellweger) head, allowing the film to toe the line between reality and fantasy while still keeping the emotions grounded. The musical numbers themselves are fabulous, and Zellweger gives a phenomenal performance for which she should have won the Best Actress Oscar. This one holds up.

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.

What Should Have Won: Moonlight

It still doesn’t entirely feel like Moonlight actually won Best Picture, due in part to the fiasco that put the La La Land team on the stage first. And while Damien Chazelle’s musical is excellent, Barry Jenkins’ Moonlight is a masterpiece of human drama. The movie’s tryptic structure constantly reminds us how quickly time passes, and how impressionable we are at young ages. Events that go by in a flash can stay with us for the rest of our lives, and shape how we react to the world around us. The magic trick of Moonlight is that despite the fact that the protagonist is played by three different actors, they all feel like the same person. That’s all due to Jenkins’ tremendous talent as a director, shaping and molding the performances and the film so that it feels entirely of a piece.

What Should Have Won: The Lord of the Rings: The Return of the King

This one is kind of cheating because if you ask me, The Fellowship of the Ring is the best Lord of the Rings film. And yet it’s hard to argue with a recognition for the trilogy as a whole coming with the final chapter, as Return of the King performed a flawless full sweep of every single category in which it was nominated. It’s a great film, and the trilogy is one of the best and most impressive cinematic achievements in movie history.

What Should Have Won: No Country for Old Men

No Country for Old Men is one of the boldest Best Picture wins in Academy Awards history. The Coen Brothers were no stranger to the Oscars having previously won the Best Original Screenplay prize for Fargo, but their Cormac McCarthy adaptation eschewed their penchant for dry humor and instead took a hard left into dramatic territory with an absolutely horrifying film about fate, the randomness of evil, and inevitability. It’s a stark, dark movie that ends with a monologue about a dream a man had, and it won Best Picture. Even more astounding is the fact that it was up against Paul Thomas Anderson’s There Will Be Blood, another stone-cold masterpiece with dark subject matter. Whether this was whiplash after the Crash fiasco or what, the Academy hasn’t quite awarded a film this brutal since. But one comes close…

Are we calling her a full-blown baddie now?

Adam Chitwood is the Managing Editor for Collider. He’s been working for Collider for over a decade, and in addition to managing content also runs point on crafts interviews, awards coverage, and co-hosts The Collider Podcast with Matt Goldberg (which has been running since 2012). He’s the creator and author of Collider’s “How the MCU Was Made” series and has interviewed Bill Hader about every single episode of Barry. He lives in Tulsa, OK and likes pasta, 90s thrillers, and spending like 95% of his time with his dog Luna.

[Read More…]