Best Actor Oscar-Winners of the 21st Century, Ranked Worst to Best

The first of Sean Penn’s two Oscars this century came in Clint Eastwood’s mournful Boston thriller. His portrayal of Jimmy, the ex-con hothead whose teen daughter is murdered, is knowingly melodramatic, full of high emotions and bubbling menace. (The scene where Jimmy learns of his child’s death overflows with operatic anguish, probably cinching his Academy Award in the process.) Penn articulates every ounce of his character’s anger and sorrow, making Jimmy both a tragic and ferocious figure. But it’s more than a touch hammy as well, which undercuts the stark realism that Mystic River otherwise achieves.

If Sean Penn’s Oscar win for Mystic River demonstrated his wiry ferocity, his turn as slain gay-rights activist Harvey Milk illustrated his sweetness and compassion. In a career personified by playing tough guys (both onscreen and off-), Penn displayed a rare gentleness here, which doesn’t mean that he wasn’t any less steely in this role. Indeed, Milk is a sort of coming-of-age film that follows its hero on a path to finding himself and, at the same time, pushing others to accept homosexuals into their communities. Penn has perhaps never been more lovable, a quality that’s rarely been associated with this actor. But look how well he wears it.

Even kings have their vulnerabilities, despite being as handsome as Colin Firth. That simple truism guides The King’s Speech, a tasteful period drama that draws its empathy from Firth’s modest, bighearted performance as King George VI, who in 1936 ascended to the throne and had to finally confront a debilitating stutter. An actor known for playing characters full of debonair charm and impeccable gentility, Firth always lets us feel the weight of the crown that lays heavy on his character’s head. Rarely has a lack of confidence been so deeply likable.

Much like Denzel Washington’s win for Training Day, Forest Whitaker snagged a Best Actor Oscar even though he’s not technically the lead in his own movie. (That would be James McAvoy’s idealistic young doctor Nicholas, who’s seduced by Whitake’s magnetic Ugandan President Idi Amin.) And like Washington’s crooked cop, the African dictator becomes a hypnotic portrait of evil — a man who generates personal warmth but can turn coldblooded if anyone crosses him. The lumbering, stoic sweetness that’s often at the forefront of Whitaker’s portrayals was stripped away completely here: In The Last King of Scotland, we only witness the unknowable wickedness of a leader whose thirst for power cannot be satiated.

Ron Woodroof, the electrician at the center of Dallas Buyers Club, isn’t the sort of guy who’s normally the focus of an Oscar-winning movie — which makes it appropriate that he’s played by Matthew McConaughey, who, for most his career, wasn’t part of any Oscar conversation. But starting with 2011’s The Lincoln Lawyer, the actor said goodbye to his beach-bum, rom-com shtick and started doing more thoughtful work, culminating in award-winning turn as a Texas homophobe who, after contracting HIV, discovers what it’s like to be discriminated against in America. McConaughey honors the man’s principled refusal to get all cuddly and inspirational just because he’s dying.

Will Smith’s infamous overreaction at the 2022 ceremony, resulting in the Slap Heard ‘Round the World, left him as something of a pariah in an industry he once ruled. But forget, for a moment, the controversy and the perhaps-permanent stain to his reputation. Smith is compelling as Richard Williams, the blue-collar Compton father convinced his daughters Venus (Saniyya Sidney) and Serena (Demi Singleton) are destined to be tennis champions — even though he lacks the financial resources their peers enjoy. The star had played inspirational true-life figures before, but in King Richard he’s not afraid to make Richard’s dedication border on unhealthy, actively questioning whether this driven father wanted his girls to succeed for themselves or to satisfy his own fragile ego. Unfortunately, The Slap eclipsed, if not erased the nuance Smith brought to the role — you can’t divorce the movie from what happened on that Oscar stage.

It’s true that eating a raw bison liver and nearly getting hypothermia while wading through freezing rivers does not guarantee you a statuette. Of course, such displays of commitment in the name of cine-autheticity certainly doesn’t exactly hinder your chances of being recognized by your voting peers, either. The backstory of how brutal the shoot was on Alejandro G. Iñárritu’s survivalist Western had become legendary by the time His Leo-ness walked up onstage to collect his first Oscar, and that almost certainly contributed to the win. But go back and watch his performance now that the hoopla has died down, and you’ll see one of his more transformative screen turns. Yes it was “time,” as many folks said in regards to DiCaprio’s victory. It was also well-deserved.

Once upon a time, Joaquin Phoenix risked becoming a parody of the self-serious artiste. Happily, he’s since righted the ship, resulting in a string of critical successes (The Master, Inherent Vice, You Were Never Really Here) — and then came the commercial colossus of Joker. The complaints that Phoenix was merely recycling a familiar onscreen M.O. as Arthur Fleck, the troubled New Yorker who will become Batman’s archnemesis, would be more persuasive if his brand of ragged unease wasn’t still so magnetic. To watch someone who’s often stayed far away from mainstream Hollywood give such a big, bold performance in a studio blockbuster is to be reminded that idiosyncratic talents can make pop art and not sully themselves in the process. Heath Ledger will forever be most everyone’s ideal Joker — unknowable, terrifying, endlessly fascinating — but Phoenix conveys all the pain that turns an ordinary man into a supervillain.

Perhaps the biggest Oscar upset since Moonlight took down La La Land, Anthony Hopkins’ second Academy Award came 29 years after his first, the voters choosing his aging patriarch battling dementia over the late Chadwick Boseman as a cocky musician in Ma Rainey’s Black Bottom. Putting aside the debate over which performance is better, let’s focus on just how superb Hopkins is in The Father — and how it was an exciting reminder of the fiery intensity the 84-year-old actor can bring to a character when he’s fully engaged. After too many years cashing in on supporting roles in mediocre blockbusters, Hopkins was a marvel as Anthony, a man who veers from extraordinarily charming to unforgivably petulant, as his disease rips away pieces of him. He shows you, step by step, how this once-mighty lion is reduced to a scared child who no longer can trust his senses or his surroundings. Did older Academy members relate to the character’s health fears? Perhaps, but viewers of any age can appreciate this layered, ultimately devastating portrait of someone watching themself slip away.

Moody, withdrawn men have been Casey Affleck’s specialty for quite some time — see Ain’t Them Bodies Saints, The Assassination of Jesse James, Gone Baby Gone. But he found the perfect vessel for his gift in the form of Lee Chandler, a working-class Bostonian whose sad life is about to get even sadder. In writer-director Kenneth Lonergan’s consummate study of loss, regret and pain, our eyes are riveted on Lee as he copes with the death of his brother and chafes at the prospect of raising his teenage nephew, developments that force him to revisit past trauma that he’s never fully escaped. Manchester by the Sea is a deep well of despondency, yet he brilliantly navigates his character’s tragic backstory, showing every ounce of the self-loathing and raw misery that Lee wears around like a baggy old sweatshirt. A lot of Best Actor triumphs come in showy, stomping roles. Affleck’s performance is still and muted, an apt portrayal of a haunted guy who wants to disappear.

Before The Pianist, this New York actor was perhaps most famous for a movie he wasn’t in, having been cut out of Terrence Malick’s The Thin Red Line. But after Roman Polanski’s Holocaust drama, Adrien Brody was a star, becoming the youngest Best Actor winner ever at age 29. His career has never again featured such a terrific role, but his later career ups and downs only amplify how singular he is as Władysław Szpilman, a Polish Jew whose life as a venerated pianist is destroyed once the Nazis invade his homeland. Brody’s performance is all haunted looks and pregnant pauses — like Leonardo DiCaprio in The Revenant, the principal job is to convey the quiet resilience required to stay alive in impossible circumstances. Brody’s soulfulness permeates this often devastatingly bleak film, his character’s simple need to survive transformed into an act of heroic defiance in the face of unimaginable atrocity.

In other hands, Ridley Scott’s neo-biblical spectacle would have just been another sturdy summer blockbuster. But Russell Crowe, who had earned kudos for previous dramatic roles in L.A. Confidential and The Insider, brought gravitas and heart to his role as an honorable Roman general who must defeat the bratty young emperor (Joaquin Phoenix) who banished him to a life in the cutthroat world of the kill-or-be-killed arena. The 21st century hasn’t produced many soulful, brooding, broad-shouldered action heroes, nor has it yielded a lot of popcorn movies with the scope and heart of Hollywood’s old-fashioned epics. Crowe and Gladiator are the exception, a rare example of a performer rising to the challenge of making a swords-and-sandals event movie that has emotional breadth. His Maximus brings down a corrupt leader — and in the process, the Aussie actor earned his place among a new generation of superstars.

Most know that Daniel Day-Lewis initially turned down Steven Spielberg’s request that he play America’s 16th president, sending the director a letter praising the brilliance of Lincoln‘s script but feeling that “I can only do this work if I feel almost as if there is no choice.” Thankfully, he changed his mind. Day-Lewis embodies Lincoln’s intelligence and stateliness, but the performance reveals more: how this shy, slightly silly, unbendingly resolute president wielded charm, intimidation, smarts and patriotism to bring an end to the Civil War while securing enough votes to pass the 13th Amendment. (His Oscar for the role made him the only man to ever win three Best Actor Academy Awards.) It took a foreign-born actor to reveal the best of the American character: our decency, our will, our humanity, our love of telling dopey jokes. Day-Lewis’ initial reluctance to play the part demonstrates why he was uniquely destined to do it so well. And it wasn’t even his best performance this century.

The tragedy of Philip Seymour Hoffman’s death in 2014 only makes this jewel of a performance more haunting. Playing Truman Capote, a snide, insecure, brilliant writer on the hunt for his masterpiece, Hoffman delivered a portrait of ambition and manipulation that never shortchanges the conflicting emotions underneath his character’s ruthless drive. In Capote, the author travels to Holcomb, Kansas in 1959 to interview the townspeople living in a community where a gruesome murder resulted in the deaths of four people. The actor views the author as part journalist and part vampire, never letting us see fully the depths of this character’s self-centeredness and callous prizing of a good story over good people’s lives. But the sneaky power of Hoffman’s portrayal is how we end up feeling sorry for this odd, smug monster anyway: It was this gifted, chameleonic, much-missed star’s finest hour.

To prepare to play Daniel Plainview, the towering, greedy misanthrope who strides the landscape like a lanky giant in There Will Be Blood, Daniel Day-Lewis studied Dust Bowl-era audio recordings, as well as tapes of actor-director John Huston. From those sources and others, he crafted one of the signature depictions of American exceptionalism writ large. Very, very large, actually: Everything about Plainview is oversized, including his avarice, pettiness, competitiveness — and especially his ruthless certainty that, somehow, sucking up all the oil in the American West will fill the void in his soul. It’s a performance that’s both endearingly gonzo and also shockingly, unexpectedly tender. But above all it’s so stunningly assured that it’s as if the actor and writer-director Paul Thomas Anderson are showing us something dark, rotten and true about capitalism itself. Oscar voters didn’t so much award him Best Actor but, rather, acquiesce to his portrayal’s indomitable, imposing magnificence.