Best Director Oscar Winners of the 21st Century Ranked From Worst to Best

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Many have suggested that a better system to award Oscars would be to wait a few years before handing them out. Give films time to breathe, and see which ones remain in the public consciousness a couple years after release, and which ones have faded. That’s not a bad idea, and is especially appealing when taking a deep-dive look back at 20 years of Oscar wins and losses. As it relates to the Best Director category, more than a few wins can be chalked up to “make-up” Oscars where the winner takes the prize for the “wrong” movie a couple years after a better one, and some reflect the notion that everyone was caught up in the heat of the moment. All these years later, are people even watching The Artist?

So let’s take a trip down memory lane and revisit the Best Director Oscar winners of the 21st century so far, ranking each win by how well it holds up, and noting who should have won for each individual year.

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20.) Ron Howard – A Beautiful Mind (2001)

A Beautiful Mind Russell Crowe

Image via DreamWorks Pictures

Who Should Have Won: Peter Jackson for The Lord of the Rings: The Fellowship of the Ring

Boy this was a weird year. A Beautiful Mind does not hold up well, nor did its subject hold up to accusations of anti-semitism. But we can’t talk about Ron Howard’s Oscar win without talking about Apollo 13. The Hollywood icon’s 1995 film was a critical darling and was earmarked as the frontrunner for all the big awards, only for Howard to be shockingly shut out of the Best Director race and for the film to lose Best Picture to Braveheart. So his win for A Beautiful Mind feels a bit like a mea culpa from the Academy, acknowledging their mistake (or for those outside the Directors branch, their frustration) with his lack of nomination in 1995. This is a thing that happens not infrequently with the Oscars – a win may not exactly match up with the right movie, but is seen as an acknowledgment of sorts of past work that was ignored or shut out.

19.) Tom Hooper – The King’s Speech (2010)

Image via The Weinstein Company

Who Should Have Won: David Fincher for The Social Network

I am still incensed about this win, so while I’m trying to be objective here, seriously WTF. Tom Hooper used some weird framing and won an Oscar for a feel-good historical drama we’ve seen countless times before, and David Fincher comes up empty handed for crafting one of the defining films of (and about) the 21st century. Dumb. Dumb dumb dumb dumb.

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

18.) Roman Polanski – The Pianist (2002)

Adrien Brody The Pianist

Image via Focus Features

Who Should Have Won: Rob Marshall for Chicago

A difficult entry for sure. As a piece of artistry, The Pianist is pretty good. Based on an autobiographical memoir, the film tells the story of a Holocaust survivor played by Adrien Brody. And as a Holocaust survivor himself, Roman Polanski certainly brought a sense of gravitas and personal experience to the film. But as is indicative of him giving his acceptance speech via satellite for fear of being arrested if he stepped foot on U.S. soil, Polanski is also a fugitive convicted of unlawful intercourse with a minor. Good movie, solid direction, bad man. Meanwhile, Rob Marshall conjured one of the best movie musical adaptations in history.

17.) Clint Eastwood – Million Dollar Baby (2004)

Hilary Swank Million Dollar Baby

Image via Warner Bros.

Who Should Have Won: Martin Scorsese for The Aviator

Coming into 2004, Clint Eastwood had a lot of goodwill from nearly running the table with Mystic River the year before. It had been awhile since Unforgiven, and the narrative was that Eastwood was back in fine form, and Mystic River kicked off a few years in which the Academy really liked recognizing whatever new Clint Eastwood movie had arrived. And Million Dollar Baby isn’t bad! It begins as a boxing drama and transitions into a dark and tragic story about its central characters, and Eastwood handles that tonal balance really smoothly. And yet it does feel like Martin Scorsese probably should have won this for his epic spin on the life of Howard Hughes, for which he mirrored the cinematography of each individual era he covered.

16.) Alejandro González Iñárritu – Birdman (2014)

birdman-set-image-alejandro-gonzalez-innaritu

Image via Searchlight Pictures

Who Should Have Won: Richard Linklater for Boyhood

There are parts of Birdman that are exhilarating, and other parts that are absolutely infuriating. But credit where credit’s due: Alejandro González Iñárritu and Emmanuel Lubezki absolutely pulled off this “one-shot” movie. While the narrative itself gets pretty naval gazing, from a technical standpoint Birdman remains impressive, and Michael Keaton delivers a hell of a lead performance. But like with The Revenant, the film leaves you wishing it had a bit more substance under all those flashy camera tricks. And yet again, Iñárritu beats out another director doing something wholly revolutionary with Richard Linklater’s Boyhood.

15.) Alejandro González Iñárritu – The Revenant (2015)

the-revenant-alejandro-inarritu-leonardo-dicaprio

Image via 20th Century Fox

Who Should Have Won: George Miller for Mad Max: Fury Road

The only director to ever win back-to-back Best Director Oscars won them for, frankly, just OK movies. If you set aside the degree of difficulty in executing The Revenant I think this lands even lower on this list, but while I’m not a huge fan of the film, I’ll admit what Alejandro González Iñárritu and Leonardo DiCaprio pulled off is impressive. This is a survival drama plain and simple, and working together with brilliant cinematographer Emmanuel Lubezki, Iñárritu puts the audience right in the headspace of DiCaprio’s lead character as he rises from a shallow grave to enact revenge. And yet it all kind of adds up to nothing new, whereas what George Miller did with Mad Max: Fury Road feels absolutely revolutionary in the annals of action cinema. Miller essentially reinvented the wheel with Fury Road, while Iñárritu simply made a very pretty wheel, and the Academy went with the latter.

14.) Ang Lee – Life of Pi (2012)

Image via 20th Century Fox

Who Should Have Won: Steven Spielberg for Lincoln

We did Lincoln dirty. In hindsight, Steven Spielberg’s biopic had far more to say about America and its politics than we gave it credit for at the time, and while Ang Lee’s technical prowess in blending CG environments and characters with his live-action lead certainly makes Life of Pi a spectacle worth witnessing, this feels like another case of us taking Steven Spielberg for granted. He’s one of the best directors in history, and when he nails it – like he did with Lincoln – he nails it. But in 2012 CG-driven blockbusters were becoming more and more prevalent, and Lee certainly did a terrific job bringing Life of Pi to life with cutting-edge technology, and the visuals he conjures are truly breathtaking. Although ask anyone which film has aged better, and I’d wager most haven’t revisited Life of Pi since it was first released.

13.) Danny Boyle – Slumdog Millionaire (2008)

danny-boyle-slumdog-millionaire

Image via Fox Searchlight

Who Should Have Won: David Fincher for The Curious Case of Benjamin Button

Slumdog Millionaire was an absolute phenomenon that took the country and the Oscars by storm in 2008, and for good reason. Danny Boyle’s kinetic filmmaking brings this fairy tale-esque story to life in a way that’s vivid yet still cinematic and ever-so-slightly untethered from reality. And while I still think the level of technical wizardry David Fincher brings to Benjamin Button maybe should’ve gotten it, Slumdog Millionaire remains one of the most entertaining Best Picture winners in recent memory.

RELATED: ‘Slumdog Millionaire’ Nearly Went Direct-to-DVD; Instead It Won Best Picture

12.) Michel Hazanavicius – The Artist (2011)

Jean Dujardin The Artist

Image via TWC

Who Should Have Won: Terrence Malick for The Tree of Life

The Artist was one of those flash-in-the-pan movies that surged at just the right time, swept the Oscars, and was never really heard from ever again. And yet, Michel Hazanavicius’ artistry in bringing silent-era Hollywood back to life is impressive, and he crafts a genuinely moving and compelling story here underneath the buzzworthy aesthetic. Is it better than the haunting poetry of Terrence Malick’s The Tree of Life? Absolutely not. But it’s pretty good!

11.) Ang Lee – Brokeback Mountain (2005)

Ang Lee Brokeback Mountain

Image via Focus Features

Who Should Have Won: Ang Lee for Brokeback Mountain

Ang Lee is hard to pin down as a filmmaker. He’s as at ease behind something like Sense and Sensibility as he is behind something like Crouching Tiger, Hidden Dragon, so it shouldn’t have been surprising when he brought a thoughtful, intimate touch to Brokeback Mountain. And while 2005 doesn’t seem that long ago, a lot has changed in the ensuing years, and at the time it was still labeled “the gay cowboy movie.” Lee’s gentle approach with his actors and confident handle on the film’s tone brought this tragic love story to life in a really beautiful way, making it all the more upsetting that it lost Best Picture to Crash the same year.

10.) Kathryn Bigelow – The Hurt Locker (2009)

Kathryn Bigelow

Image via Summit Entertainment

Who Should Have Won: Kathryn Bigelow for The Hurt Locker

It’s been over 10 years since Kathryn Bigelow became the first woman to win the Oscar for Best Director, and while history could be made again this year, Bigelow’s win still holds up tremendously as one of the Oscars’ boldest decisions. James Cameron’s technical wizardry of Avatar was tempting, but in a shock to many, Bigelow pulled out the win for her candid, affecting portrait of PTSD during the Iraq War. It’s a testament to Bigelow’s filmmaking that The Hurt Locker excels as both a nail-biting thriller and a provocative chronicle of the lives of soldiers, and the difficulty in living daily life after being on-edge at all hours of the day abroad. There were plenty who thought Cameron would be King of the World once more, and I still can’t quite believe Bigelow took this one home.

9.) Steven Soderbergh – Traffic (2000)

Image via USA Films

Who Should Have Won: Steven Soderbergh for Traffic

It’s still insane that Steven Soderbergh not only was nominated for Best Director twice in the same year, but won instead of splitting the votes. Traffic and Erin Brokovich could not be more different films, and yet they showcase Soderbergh’s strengths as a filmmaker – his tenacity, ambition, creativity, and terrific eye for character. Traffic was a pretty radical departure for the director, but his epically intimate chronicle of the War on Drugs through three very different points of view (each with a distinct aesthetic) is tremendously effective and cinematic all at once. And while an argument could be made that Ridley Scott should’ve won for Gladiator (that year’s Best Picture-winner), I think Soderbergh’s win has aged wonderfully as one of the Academy’s best decisions.

8.) Damien Chazelle – La La Land (2016)

la-la-land-damien-chazelle-emma-stone

Image via Summit Entertainment

Who Should Have Won: Damien Chazelle for La La Land

Haters gonna hate and all that, but La La Land is a terrific film and Damien Chazelle’s direction is downright phenomenal. He conjures a colorful, candy-coated musical ode to Los Angeles and dreamers that’s also a deeply felt love story and a harsh film about expectations vs. reality, and how we react when we meet a crossroads in our lives. The tonal tight-rope walk is a thing to behold, and it’s a testament to Chazelle’s talent that a scene in which the two lead characters float into the sky doesn’t detract but instead depens your connection to – and investment in – their romance and well-being.

7.) Guillermo del Toro – The Shape of Water (2017)

the-shape-of-water-guillermo-del-toro

Image via Fox Searchlight

Who Should Have Won: Guillermo del Toro for The Shape of Water

Guillermo del Toro straight up remade Creature from the Black Lagoon with sex, and won an Oscar for it in the process. The Shape of Water is a film that absolutely should not work, and for that reason alone GDT was the only human being on the planet capable of making this film. His entire career is built on the stories of outsiders, and indeed The Shape of Water is a movie entirely populated by characters who are othered – Sally Hawkins’ empathetic mute; Richard Jenkins’ closeted aspiring artist; Octavia Spencer’s strong-willed maid who’s told she’s less than simply because of the color of her skin; and of Doug Jones’ literal fish man. These are characters Del Toro understands deeply, and their stories soar thanks to his meticulous direction that values symbolism and theme in shot composition and camera movement. Guillermo del Toro’s first Best Director Oscar was a long time coming, and he won for one of his purest artistic statements.

6.) Alfonso Cuarón – Roma (2018)

roma-alfonso-cuaron

Image via Netflix

Who Should Have Won: Alfonso Cuarón for Roma

Alfonso Cuarón doesn’t make many films, but when he does… look out. Roma is personal to the point of therapy in that Cuarón literally recreated his childhood home and had actors re-enact extremely specific memories from his upbringing, and yet the film does not feel like a vanity project. Instead, it feels almost experimental or progressive in its effect, as Cuarón’s ultra-high-definition black-and-white photography doesn’t flash back to memories, it conjures them fully formed, for all to see and hear and feel on the big screen. Watching Roma is an exercise in empathy as we see the world of this family through the eyes of young Yalitza Aparicio’s Cleo, but the trick to Roma is in Cuarón’s filmmaking. Watching the movie scene-by-scene has a cumulative effect, as Cuarón builds moments on top of one another until you get to the finale and are overwhelmed with emotion, bursting into tears for reasons that aren’t entirely clear beyond how deeply you feel for the characters onscreen. That’s the magic of the movies.

5.) Martin Scorsese – The Departed (2006)

The Departed Martin Scorsese

Photo by Warner Bros/Kobal/Shutterstock

Who Should Have Won: Martin Scorsese for The Departed

Okay yes, Martin Scorsese should have won the Best Director Oscar at least two times before – if not more – but that doesn’t make The Departed or his work therein any less great. After making “Oscar movies” with Gangs of New York and The Aviator, Scorsese merely attempted to make a great popcorn movie with The Departed and ended up winning his first-ever Best Director Academy Award. The film is a crime thriller on an epic scale, but it’s packed with the character and meaty themes you expect from a master filmmaker like Scorsese.

4.) Alfonso Cuarón – Gravity (2013)

Gravity Alfonso Cuaron

Image via Warner Bros.

Who Should Have Won: Alfonso Cuarón for Gravity

Alfonso Cuarón is a bit of a magician, and Gravity remains one of his best tricks. It’s a deceptively simple film – it’s a survival story in the vein of Cast Away, except Sandra Bullock is trapped in space instead of on an island. But the technological wizardry that Cuarón quite literally invented to bring these images to life is straight up awe-inspiring. Eight years later and I still can’t quite work out exactly how they did most of what they did in this movie, and that keeps the magic intact. Moreover, the jaw-dropping visuals are all in service of a simple allegorical story full of symbolism, in which Bullock’s character is reborn as she works through her past trauma to, literally, get back on her feet.

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

Peter Jackson The Lord of the Rings

Image via Warner Bros.

Who Should Have Won: Peter Jackson for The Lord of the Wrings: The Return of the King

While Peter Jackson frankly should have won his first Oscar for The Fellowship of the Ring, it was still supremely satisfying to see him onstage in 2003 accepting the Oscar for capping the trilogy with Return of the King. In truth, the record-tying 11-win run for Return of the King was really an acknowledgment of the trilogy as a whole, and a wholly deserving one at that. It’s one of the greatest cinematic accomplishments of all time, with Jackson and Co. filming all three Lord of the Rings movies simultaneously and then fleshing each film out with additional footage over the next three years. It’s a truly iconic piece of cinema, and even with Return of the King’s seven different endings, it stands as one of the best films ever made. Jackson’s win remains one of the most deserving Oscars in history.

2.) The Coen Brothers – No Country for Old Men (2007)

Coen Brothers

Image via Miramax

Who Should Have Won: The Coen Brothers for No Country for Old Men

2007 is proof positive that the Academy can be bold and surprising at times. No Country for Old Men is a severe, ambiguous, unsatisfying drama about the uncertainty and randomness of life (and death), and how every decision we make means everything at nothing all at once. And it won Best Picture, Director, Adapted Screenplay and more. It’s crazy to think this was Joel and Ethan Coen’s first Best Director Oscar win, but it was wholly deserving. And this was in a year in which they were up against another masterpiece, Paul Thomas Anderson’s There Will Be Blood. A close call to be sure, but the Oscars got it right.

1.) Bong Joon-ho – Parasite (2019)

parasite-bong-joon-ho-set-photo

Image via Neon

Who Should Have Won: Bong Joon-ho for Parasite

When considering #1 on this list, I took into account a deserving win for a deserving film. Martin Scorsese is one of the greatest directors who ever lived, but The Departed is far from his best film. The Coen Brothers come close with No Country for Old Men, but something about the mix of absolute shock and satisfaction of seeing Bong Joon-ho win for his masterful drama Parasite just feels right. Like some others on this list, it’s still a little hard to believe it actually happened, but the Korean-language film deservedly cleaned up on Oscar night as the Academy acknowledged Joon-ho’s brilliant, incisive warts-and-all portrait of capitalism. Director Bong is a perfectionist, and every single moment in Parasite feels expertly choreographed and hand-picked, but not to the point of smothering the art itself. It’s purposeful, as if Bong is guiding the viewer along this odyssey that really lays bare the effects of capitalism and the sad illusion of socio-economic mobility.

Parasite feels like a house of cards – one wrong move and the whole thing comes tumbling down. It builds and builds until it opens trap doors and secret passageways that delight from a plot perspective, but also further the thematic thrust of the film. It’s a masterpiece, and Bong Joon-ho is a master.

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About The Author

Adam Chitwood
(15691 Articles Published)

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.

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