Best Actor Oscar Winner of the 21st Century

Which winners were deserved? Which were mistakes? Which performances have stood the test of time, and which have faded from memory? This trip into the past is hopefully a fun way to consider what the Oscars actually mean and to recall and celebrate some truly brilliant performances from the past two decades.



Every Best Actor Oscar Winner of the 21st Century Ranked from Worst to Best.


20.) Rami Malek – Bohemian Rhapsody (2018)

Who Should Have Won: Bradley Cooper in A Star Is Born

Rami Malek’s turn as Freddie Mercury in Bohemian Rhapsody is not a bad performance. But is it the stuff Oscars are made of? It depends on who you ask. This is the quintessential “showy” performance that can so often lead to Oscar glory – fake teeth, wigs, audio mixed with Freddie Mercury’s actual singing voice. But underneath all the glitz and glamor is there really that much substance there? Bohemian Rhapsody has its moments, almost exclusively made by Malek and his performance, but on the whole Bryan Singer’s biopic is a sanitized version of the truth that borders on offensive. In hindsight, it’s all the more infuriating that Malek took the prize here over Bradley Cooper pouring his dang heart out in A Star Is Born.


19.) Jean Dujardin – The Artist (2011)

Who Should Have Won: Brad Pitt in Moneyball

Here’s a fun fact: The Artist is a feature film that was released to audiences and won five Oscars including Best Picture, Best Director, and Best Actor. It’s undoubtedly one of the most obscure Oscar juggernauts in history – a perfectly fine if forgettable ode to the silent era. Its gimmick worked its magic in those couple of months that it was on the Oscar campaign trail, and Jean Dujardin – a fine performer – took home the Best Actor Oscar prize for his charming silent performance. Again, it’s a fine movie and a fine performance, but The Artist began to fade from our collective memory the very night it took home all these prizes.


18.) Colin Firth – The King’s Speech (2010)

Who Should Have Won: Jesse Eisenberg in The Social Network

I am still mad that The Social Network lost Best Picture to The King’s Speech, but I’m also mad that Jesse Eisenberg lost Best Actor to Colin Firth. The latter is an incredibly talented performer and no doubt was due to land on the Oscars stage at some point, but The King’s Speech is such a trite little film for which to win. But this fits another one of the Oscars’ favorite categories, which is “famous A-lister plays someone struggling through a physical challenge against the odds.” This won’t be the last one of these you see on this list.


17.) Russell Crowe – Gladiator (2000)

Who Should Have Won: Tom Hanks in Cast Away

Russell Crowe is very good in the Best Picture-winning Gladiator, but his Oscar win in 2000 was very clearly a make-up for him losing the year before. Indeed, Crowe wholly deserved the Best Actor trophy in 1999 for his stunning turn in Michael Mann’s The Insider, but that year’s prize went to Kevin Spacey for American Beauty. Sometimes when the Academy gets it wrong, voters feel a sense of remorse and end up awarding that performer or filmmaker later on for a less remarkable piece of work (see also: Al Pacino in Scent of a Woman). That’s really what happened here, because while Gladiator is a rousing sword-and-sandals epic, Crowe doesn’t quite hit the depths he hit while playing a whistleblower in The Insider.


16.) Adrien Brody – The Pianist (2002)

Who Should Have Won: Nicolas Cage in Adaptation.

Adrien Brody is very good in The Pianist, a film that’s kind of faded from memory. Nicolas Cage is next-level great in Adaptation., a brilliant story from the mind of Charlie Kaufman that’s still being talked about today.


15.) Sean Penn – Mystic River (2003)

Who Should Have Won: Bill Murray in Lost in Translation

Sean Penn’s devastating line-reading of “Is that my daughter in there?” in Clint Eastwood’s grief drama Mystic River is probably what single-handedly won him the Oscar that year. And it’s a good performance! This film started a run of Eastwood films that made him an Academy darling, with Mystic River losing most of its trophies to the juggernaut that was The Lord of the Rings: The Return of the King. But Penn’s performance remains one of the better “grief-stricken father” Oscar-winning turns.



14.) Jamie Foxx – Ray (2004)

Who Should Have Won: Leonardo DiCaprio in The Aviator

Here’s another historical figure performance boasting a full physical transformation, and indeed Jamie Foxx is damn near unrecognizable as Ray Charles in Taylor Hackford’s cradle-to-grave biopic. The film Ray is extremely by-the-numbers, but sometimes that doesn’t really matter when you have a performance this striking. Foxx fully becomes Ray Charles, warts and all, and it’s an impressive achievement. Some thought Leonardo DiCaprio had an edge this year with his equally impressive turn in The Aviator, but the Academy largely snubbed Martin Scorsese’s own epic biopic. I still feel DiCaprio’s performance is the more impressive, but there’s no denying Foxx is great in Ray.


13.) Jeff Bridges – Crazy Heart (2009)

Who Should Have Won: Jeff Bridges in Crazy Heart

Jeff Bridges will break your heart in Crazy Heart, the emotional story of an alcoholic country singer who gets one last shot at redemption. It’s the kind of performance-driven film that’s prone to land acting nominations, but Bridges’ legacy and stature certainly created an air of “it’s his time” when it came to settling on the winner. And it’s impossible to be mad at it, because it’s a really great performance.


12.) Forest Whitaker – The Last King of Scotland (2006)

Who Should Have Won: Forest Whitaker in The Last King of Scotland

The win for Forest Whitaker the year of The Last King of Scotland was a long time coming, and while the film itself hasn’t really held up as a must-see classic or anything, Whitaker’s performance remains terrifying. The veteran performer breathes life into dictator Idi Amin, as told through the eyes of a young physician (James McAvoy). What’s so impressive about Whitaker’s performance is you find Amin charming… up until you don’t. It’s a window into how dictators like Amin are able to rise to power, as Whitaker digs deep into the character to root his performance in the fatal flaws that make Amin so dangerous.


11.) Eddie Redmayne – The Theory of Everything (2014)

Who Should Have Won: Steve Carell in Foxcatcher

Here’s another case of “actor plays a historical figure with a lot of makeup and wins an Oscar,” but honestly it’s hard to blame them when it comes to Eddie Redmayne’s turn as Stephen Hawking. It’s a genuinely impressive performance, and The Theory of Everything is above average for most biopics of its ilk. Steve Carell’s full immersion in Foxcatcher was absolutely terrifying, but few found the strength or patience to stomach Bennett Miller’s measured, meticulous drama. When in doubt, “showy” wins, but Redmayne’s prize here is tough to argue against.


10.) Sean Penn – Milk (2008)

Who Should Have Won: Mickey Rourke in The Wrestler

2008 was an intensely competitive Best Actor race that came down to the wire, and while I think Mickey Rourke probably deserved to win for his soul-baring performance in The Wrestler, there’s no denying Sean Penn is extremely good in Milk. Gus Van Sant’s biopic of the first openly gay man to be elected to public office in California is a sensitive and tragic film, and Penn does a swell job of getting to the heart of what made Harvey Milk so personable. There’s a slight feeling of “straight actor gets an award for ‘bravely’ portraying a gay man” here, but again I think Penn’s performance is quite good regardless.



9.) Leonardo DiCaprio – The Revenant (2015)

Who Should Have Won: Michael Fassbender in Steve Jobs

And here we come to the ultimate “he was due” or “it was his time” win for the absolute wrong movie. Leonardo DiCaprio has given a number of Oscar-worthy performances in his lifetime, and while he certainly gives it his all in The Revenant, I can’t shake the feeling that film is less performance and more “physically put through hell on camera.” Yes I know, it’s a very method turn (he ate raw bison liver, he got very cold), but in the pantheon of great DiCaprio performances, I’m not sure this one holds up as well as The Wolf of Wall Street or Django Unchained or Catch Me If You Can. Again, it’s a good performance – he’s one of our best living actors – and there’s no doubt he put himself through the wringer for it, I just wish he’d have finally won his Oscar for a better film.


8.) Matthew McConaughey – Dallas Buyers Club (2013)

Who Should Have Won: Leonardo DiCaprio in The Wolf of Wall Street

Speaking of physical transformations, Matthew McConaughey eschewed prosthetics or digital effects for Jean-Marc Valle’s gritty AIDS drama Dallas Buyers Club, shedding a ton of weight to portray an AIDS patient who smuggled unapproved drugs into Texas for distribution. The film solidified the “McConaissance” and for good reason – this isn’t McConaughey putting on a brave face or mugging for the camera. This performance feels borne out of the actor’s soul, reaching emotional depths he had thus far not been given the opportunity to portray onscreen. It’s pretty great, although I’d be remiss if I didn’t mention The Wolf of Wall Street is quite possibly the best performance of Leonardo DiCaprio’s career thus far.



7.) Gary Oldman – Darkest Hour (2017)

Who Should Have Won: Gary Oldman in Darkest Hour

Not all physical transformations come off as Oscar bait-y. The makeup that transformed Gary Oldman into Winston Churchill is truly mind-blowing, but it’s the performance underneath that makes his turn Oscar-worthy. Oldman disappears into the role to be sure, but he also brings this historical figure to life in a way that makes him and his impact relatable. You can see the conflict within Churchill, the empathy, and the motivations that drove his extremely important decisions throughout World War II. Oldman was due, and for once, this actor won for a truly Oscar-worthy performance.


6.) Joaquin Phoenix – Joker (2019)

Who Should Have Won: Adam Driver in Marriage Story

Whatever you think about Joker, it’s impossible to deny that Joaquin Phoenix is excellent in it. Physically, emotionally, mentally – Phoenix fully inhabits this role and commits to Arthur Fleck’s story arc that eventually turns him into The Joker. It’s at turns tragic and sickening, and further shows the depths to which Phoenix will go for a role. He makes some wild choices here and they almost always work, but of course, we’ve known this for years after stunning turns in films like The Master. Even as someone who didn’t really love Joker, it was hard for me to argue with Phoenix’s win – I can absolutely understand it. Even if Adam Driver actually gave the performance of the year in Marriage Story.


5.) Casey Affleck – Manchester by the Sea (2016)

Who Should Have Won: Casey Affleck in Manchester by the Sea

Grief is an emotion that’s hard to manifest onscreen, although many, many, many have tried. But what Casey Affleck does in Kenneth Lonergan’s brilliant drama Manchester by the Sea is both unexpected and deeply human. Here’s a man who cannot bear to forgive himself for one grave mistake, and it’s dictated his entire life ever since. There’s an unceasing pain underneath, and no matter how close he seems to come to the surface, he can’t stop himself from drowning. It’s one of the most heartbreaking, gut-wrenching performances to ever win an Oscar, and for once the Academy recognized that subtlety is often even more impressive than “Big” emotions.


4.) Philip Seymour Hoffman – Capote (2005)

Who Should Have Won: Philip Seymour Hoffman in Capote

It still hurts to remember that Philip Seymour Hoffman is gone, knowing he had so many more incredible performances to give us. He won an Oscar for his role as Truman Capote in Capote, disappearing into the role while bringing a sense of empathy to the iconic writer as the film chronicles the writing of In Cold Blood. The range of this man, to go from something like Boogie Nights to The Master to Capote – all wildly divergent performances, all brilliant in their own way.


3.) Denzel Washington – Training Day (2001)

Who Should Have Won: Denzel Washington in Training Day

Denzel Washington owns Training Day. To the point that you don’t really care about the glaring plot holes in the third act because you’re so mesmerized by his performance. “King Kong ain’t got shit on me” has become the most quotable line from the film, but it’s actually emblematic of Washington’s entire approach to playing this corrupt cop. He stomps around like King Kong himself – impervious to the threat of violence or the law, doing whatever pleases or amuses him from minute to minute. He is as terrifying as he is beguiling, and Washington absolutely nails this balance. Denzel Washington is one of those actors like Tom Hanks or Meryl Streep who we take for granted because they’re so consistently great, but man is he great in this film – one of the few times Washington has dipped his toe into playing a despicable character. His historic Oscar win was well-deserved.


2.) Daniel Day-Lewis – Lincoln (2012)

Who Should Have Won: Daniel Day-Lewis in Lincoln

It’s become cliché to say Daniel Day-Lewis is one of the greatest actors of all time, but dammit he’s genuinely one of the greatest actors of all time. To watch Steven Spielberg’s somewhat underrated masterpiece Lincoln is to witness an American president wrestle with the burden of power. Day-Lewis wholly transforms here, from voice to posture to gait, but this isn’t merely a fancy performance full of bells and whistles. It’s all in service of Day-Lewis inhabiting this role so deeply that his every word, gesture, and glace are telling you about the emotional and mental state of Abraham Lincoln. What makes the film so remarkable is that it’s really a process story – a nuts-and-bolts chronicle of how American politics actually works, rife with frustration, prejudice, and a little bit of corruption. Watching Day-Lewis’ Lincoln wrestle with whether pushing the 13th Amendment is the right thing to do, or whether he actually truly had the power to enact the Emancipation Proclamation, is unendingly compelling, aided by Spielberg’s masterful blocking and shot composition. This is no standard biopic. It’s a living document, and Day-Lewis makes it soar.



1.) Daniel Day-Lewis – There Will Be Blood (2007)

Who Should Have Won: Daniel Day-Lewis in There Will Be Blood

Honestly, #1 and #2 here could be a tie. And maybe they should have been. But I will give a slight edge to There Will Be Blood for Daniel Day-Lewis creating a character from the ground up vs. portraying a historical figure, just for the level of difficulty. Daniel Plainview is a brilliant, despicable, craven human being who is the embodiment of American capitalism, and what makes Day-Lewis’ performance so phenomenal is you both absolutely loathe him and yet are still kind of rooting for him to succeed. Paul Thomas Anderson’s film is a dense picture packed with complicated emotions and distressing themes, but Day-Lewis is its beating, black heart.

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