Next month, there will be a new Best Supporting Actor winner at the Academy Awards. With nominees likeKodi Smit-McPhee(The Power of the Dog),Troy Kotsur(CODA),Ciaran Hinds(Belfast), and more, someone great will absolutely be joining the ranks of this long, ever-evolving roster. The past ten years have shown a marked evolution, as the Academy grows steadily more diverse and more willing to fly against typical Oscar conventions. As such, it’s worth ranking the past ten winners in this category, to see how they measure up against each other and serve as part of this larger narrative. While none of these performances are outright bad (even the weakest has some redeeming qualities), some are stronger than others. And so, without further ado…
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10. Jared Leto in Dallas Buyers Club (2013)
It’s difficult to imagineJared Letobeing cast as trans prostitute Rayon inDallas Buyers Clubtoday, let alone winning an Oscar for the role. But even putting aside the ethics of casting him over a trans actor, Leto is easily the weakest link of these ten performances. There’s something naggingly inauthentic about Leto’s Rayon, with her breathy Southern drawl and sassy, mincing demeanor. AlthoughDallas Buyers Clubis based on a true story, Rayon is an invention of the film, and it shows.
There are moments where Leto successfully conveys the grit and gallows humor of a woman in a terrible situation: when Rayon’s bigoted father sighs “God help me,” she sneers back “Heishelping you, I’ve got AIDS.” But elsewhere, as when Rayon tearfully applies makeup and tells God that she wants to look pretty for Him when she dies, it feels like a moment of risible melodrama, a parody of mawkish Oscar bait.

9. Sam Rockwell in Three Billboards Outside Ebbing, Missouri (2017)
One of the ways the Academy uses the Supporting categories is to recognize a talented, hard-working actor who has paid their dues, even if they didn’t necessarily give a towering performance that particular year.Sam Rockwellis one of those actors: he had already given several awards-worthy performances by the time he got an Oscar nod forThree Billboards Outside Ebbing, Missouri, in movies likeMoonandThe Way, Way Back. It was hard to root against him.
As usual, Rockwell does fine work as Jason Dixon, a racist, alcoholic police officer who butts heads with the crusading mother of a murder victim (Frances McDormand). He’s compulsively watchable as an obnoxious bully, lumbering and uncertain and more than a little funny. It makes his turn towards redemption in the second act an easier pill to swallow, as the audience is able to believe that he was merely stupid rather than evil. But in a year with performances as strong asWillem DafoeinThe Florida ProjectorMichael StuhlbarginCall Me By Your Name, was Rockwell really the best choice?

8. Mark Rylance in Bridge of Spies (2015)
Perhaps the world wasn’t ready for Academy Award WinnerSylvester Stallone. While his reprisal of Rocky Balboa inCreedearned him buzz and a Golden Globe, the Oscar ultimately went toMark RylanceforBridge of Spies. Was it a safe choice from an Academy that didn’t want to give an Oscar to the star ofStop! Or My Mom Will Shoot?Perhaps, but it’s hard to say Rylance is undeserving.
As Rudolf Abel, a captured Soviet spy who becomes a key part of a Cold War prisoner exchange, Rylance gives a quiet, restrained performance without many obvious “Oscar moments.” Still, he manages to make Abel the most likable, compelling character in the movie, which is no small feat when starring oppositeTom Hanks. In Rylance’s hands, Abel is an eloquent, honorable man, sincerely committed to a cause greater than himself; he just happens to be on the other side of a geopolitical divide.

7. Christoph Waltz in Django Unchained (2012)
No, it’s not quite as memorable asChristoph Waltz’ other Oscar-winning turn in aQuentin Tarantinofilm. And yes, the fact that Waltz won overPhilip Seymour Hoffman’s instantly legendary performance inThe Masterstings a bit. Still, that doesn’t change the fact that Waltz’ character inDjango Unchainedtotally owns. An eccentric German dentist/bounty hunter, Dr. King Schultz frees the titular Django (Jamie Foxx) from slavery and helps him seek vengeance.
In less careful hands, Schultz could have been a series of affectations in search of a character. He drives around in a carriage with a giant tooth on the top, he introduces his horse to people, and he speaks in flowery, elaborate sentences. But Waltz ties it all together, imbuing Schultz with puckish charm, sincere compassion, and a steel-trap mind constantly at work behind his twinkling eyes.

6. Mahershala Ali - Green Book (2018)
From the momentGreen Bookwas announced as the winner of Best Picture at the 91st Academy Awards, it wasn’t just seen as a bad choice; it was seen as anembarrassingchoice, a return to the days ofCrash. But while it shouldn’t have won two of its three Oscars, there was one it richly deserved.
Winning his second Oscar just two years after his first,Mahershala AliisGreen Book’s saving grace. As Dr. Don Shirley, a Black pianist traveling with his chauffeur/bodyguard through the Jim Crow South, Ali is a portrait of quiet dignity. At the start of the movie, Don is reserved and even standoffish, but Ali is careful not to overplay it: he’s not a snob, he’s just a fiercely intelligent man who has learned to keep his guard raised at all times. If his unlikely friendship with Tony Vallelonga (Viggo Mortensen) feels a bit forced, Ali does everything he can to ground it in reality, lending heart and wry humor to even the most cringe worthy moments.
5. Christopher Plummer in Beginners (2010)
Despite a long and storied career, the lateChristopher Plummerwas only nominated for Oscars in the last full decade of his life; when he won Best Supporting Actor for his role inBeginners, he was eighty-two years old. But if he had to wait that long for Oscar gold, at least he got it for a great performance.
Mike Millswas still coming into his own as a director when he madeBeginners, and there are definitely moments where it feels too twee for its own good. But it’s held together by Plummer’s performance as Hal Fields, the protagonist’s elderly father who came out as gay late in life. Oliver (Ewan McGregor) initially resents the fact that his dad kept an unhappy marriage going for over forty years, only embracing his sexuality after the death of his wife. Eventually, he comes around, and who can blame him? Only the hardest of hearts would deny the pleasure of seeing Plummer positively glowing with joy, rejuvenated and filled with purpose. It’s appropriate that Plummer would win his Oscar by embodying an octogenarian unexpectedly entering his prime.
4. Daniel Kaluuya in Judas and the Black Messiah (2021)
Judas and the Black Messiahhas two leads, but not according to the Oscars. BothLakeith StanfieldandDaniel Kaluuyaended up in the Supporting category, despite being obvious co-leads. But there was no vote-splitting: Kaluuya easily won for his performance as Fred Hampton anyway.
There was never really any doubt. As Fred Hampton, Kaluuya is more than just a charismatic leader: he’s a sizzling stick of dynamite. He’s the kind of man who changes the aura of the room the second he walks inside. His speeches are intense enough that, when they finish, viewers might notice they had been holding their breath the whole time. Kaluuya may not look much like Fred Hampton, but physical resemblance is less important than embodying a person’s essence: watching him, the viewer understands exactly why he inspired such passion, and exactly what a tragedy his betrayal was.
WhenBrad Pittwon his first acting Oscar for his role as Cliff Booth inOnce Upon a Time…in Hollywood, it was commonly understood as recognition for his career rather than that particular performance. Nobody really hated Pitt’s performance, but everybody had one they liked better: Willem Dafoe inThe Lighthouse, orSong Kang-hoinParasite. But not only did Pitt deserve the Oscar (well, since Dafoe wasn’t nominated, anyway), he is an essential part of what madeOUATIHsuch a generous, rewarding movie.
Consider, for a moment, how insufferable Cliff Boothcouldhave been. The stuntman for fading star Rick Dalton (Leonardo DiCaprio), Cliff is shown to be an unshakeable badass who is shown beatingBruce Leein a fight. That’s the kind of macho power fantasy high school boys doodle in the margins of their math notes. The fact that he’s implied to have killed his wife doesn’t help. And yet, thanks to Pitt, Cliff is one of the most likable characters Quentin Tarantino has ever created. Irresistible as a man of simple tastes and beguiling chill, every line delivery is like a miniature vacation. (Personal favorite: that drawn-out “yeeeeah!” when he’s watching TV in his trailer.) Through Pitt, Cliff embodiesOUATIH: relaxed, amiable, occasionally violent, and a treat to watch.
2. J.K. Simmons in Whiplash (2014)
Terence Fletcher is an imposing figure from the moment he first appears. Clad in an all black outfit that emphasizes his sinewy frame, his default facial expression is a craggy scowl that wouldn’t look out of place on a gargoyle. His voice is a gruff, authoritative baritone, the voice of God as imagined by someone onverypoor terms with their father. Even when he presents himself as a tough-but-fair mentor, he makes viewers uneasy; by the time he starts throwing chairs and bellowing insults at his students, he’s a figure of Old Testament dread.
It’s impossible to imagine anyone butJ.K. Simmonsin the role of Fletcher,Whiplash’s sadistic music instructor who torments his students in the name of “greatness.” The veteran actor has a way of leaving his mark on a part, and Fletcher is perfectly calibrated to his strengths. A jazz musician who acts like a drill sergeant could have been comically over-the-top, but there’s genuine venom and menace behind even his most baroque insults. At the same time, Simmons inspires a certain awe: as terrifying as Fletcher is, it’s easy to understand why Andrew Neiman (Miles Teller) would drum until his fingers bled to try and please him. Fletcher may think “good job” are the two most dangerous words in the English language, but with Simmons it’s an understatement:outstandingjob.
1. Mahershala Ali in Moonlight (2016)
It might have been the first hint that change was afoot. The eventual winner wasn’t an underdog, not exactly; he had won a SAG Award, after all. But still, this was theOscars. Very little gets done without expensive FYC campaigns, and the master of that particular dark art, Harvey Weinstein, hadn’t been publicly disgraced yet. The eventual winner had passion on his side, but would that be enough for such a subtle performance? It was reasonable to assume that the Academy would take the predictable route once again, giving Best Supporting Actor to someone likeDev PatelinLion.
But they didn’t. Instead, the Academy did what they should do every year: they gave the award to the unambiguous best performance in the category. They gave the award to a performance of utter compassion and sensitivity, a finely-wrought portrayal of a man showing tenderness to a child who desperately needs it. They gave the award to a performance that brought oceanic depth to a figure that lesser movies use as an archetypal villain: a Black drug dealer. They gave the award to a performance that, through the lyrical beauty of its signature swimming scene, could wring tears from a stone.
They gave the award to Mahershala Ali inMoonlight. As the Academy grows younger and more diverse, let’s hope that they continue to make inspired choices like this.