There are some truly wonderful good guys among the Oscars’ best supporting actor performances this century. There’s also a Nazi villain, a band director from hell and even a Joker.
At the Academy Awards, the category has had its share of antagonists, like Robert Downey Jr.’s vengeful politico in Christopher Nolan’s “Oppenheimer” or Javier Bardem’s psycho killer in “No Country for Old Men.” And while newly minted Oscar winner Kieran Culkin’s character is a bit of a mess in “A Real Pain,” he winds up closer to Mahershala Ali’s paternal drug dealer in “Moonlight” than, say, a supervillain.
In honor of Culkin’s win – and in anticipation of someone else joining the canon in 2026 – we’re ranking all the best supporting actor winners of the past 25 years.
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25. Christoph Waltz, ‘Django Unchained’ (2013)
In Quentin Tarantino’s Western revenge flick, Waltz conjures a nifty bit of chemistry with Jamie Foxx for a different sort of buddy dynamic: King Schultz (Waltz) is a German dentist and bounty hunter who frees the enslaved man Django (Foxx) and then they partner up on a rescue mission to Mississippi to find Django’s wife.
24. Chris Cooper, ‘Adaptation’ (2003)
Cooper goes all in with an over-the-top personality in this very strange meta dramedy. Screenwriter Charlie Kaufman (Nicolas Cage) has an existential crisis trying to adapt “The Orchid Thief” by Susan Orlean (Meryl Streep), and Cooper’s John Laroche is a flower-stealing Florida man (and Susan’s secret lover) embroiled in an absurd murder plot.
23. Jim Broadbent, ‘Iris’ (2002)
Featuring Kate Winslet and Judi Dench as famed novelist Iris Murdoch in her younger and older years, the biopic is also a moving drama about the effects of dementia on patients and loved ones. Broadbent is quite good as the elder Iris’ husband John, struggling through worries and frustrations as her Alzheimer’s disease worsens.
22. Morgan Freeman, ‘Million Dollar Baby’ (2005)
The best picture-winning boxing drama paired up-and-coming boxer Maggie (Hilary Swank) with grumpy reluctant coach Frankie (Clint Eastwood). The usual sports movie template gets a welcome tweak with Freeman, whose gym assistant Scrap is a wise, grounding presence for both Maggie and Frankie as they navigate personal issues.
21. Benicio del Toro, ‘Traffic’ (2001)
Steven Soderbergh’s crime drama looks at the drug trade from various perspectives, and del Toro’s rock-steady performance is one of the highlights – a nice job amid a litany of not-always-nice characters. He plays a Mexican cop hired by a general to take out a cartel hitman, the situation goes south but he still finds a way to do right.
20. Christian Bale, ‘The Fighter’ (2011)
Unnervingly thin and hot tempered, Christian Bale plays Dicky, a former boxer and crack addict who trains his younger half-brother Micky (Mark Wahlberg) for a championship fight, though is not the best influence. They bicker and fight in the true-life sports drama, and Bale exudes a gonzo frenetic energy with an underlying melancholy.
19. George Clooney, ‘Syriana’ (2006)
Even with some extra weight and bushy facial hair, Clooney can’t hide his talent for imbuing watchable humanity into a role. In a political thriller with intertwining story lines, the A-lister stars as a veteran CIA agent who uncovers an assassination plot in the Middle East. His efforts to stop it brings a bunch of trouble (and a little torture).
18. Mark Rylance, ‘Bridge of Spies’ (2016)
The English actor was a relatively unknown commodity on this side of the pond but became a brilliant revelation for his role in the Cold War thriller as a quiet, older Brooklyn man arrested for being a Soviet spy. Opposite Tom Hanks, Rylance emits an icy intensity but also a kindness as his character waits for whatever fate chooses for him.
17. Ke Huy Quan, ‘Everything Everywhere All at Once’ (2023)
Quan’s comeback, from 1980s child star to selfie-taking Oscar winner, is one of Hollywood’s more crowd-pleasing narratives in recent years. He’s also just fun to watch in the trippy genre mashup thanks to a multifaceted role filled with alternate personalties, from a kind laundromat owner to an alpha martial-arts master from the future.
16. Sam Rockwell, ‘Three Billboards Outside Ebbing, Missouri’ (2018)
The darkly comic crime drama pits Frances McDormand’s righteously furious mom against a police force that hasn’t caught her daughter’s killer. Rockwell’s Officer Dixon, a mama’s boy with a screw loose and a history of torturing Black prisoners, is a target of her ire − that is, until the actor carefully adds layers to what could be a one-note jerk.
15. Mahershala Ali, ‘Green Book’ (2019)
The period dramedy ended up being a somewhat controversial best picture winner. Ali, on the other hand, is spot-on as a renowned classical pianist who goes on a tour of the Jim Crow South with a New York tough guy (Viggo Mortensen) and puts on aristocratic airs that belie his insecurities.
14. Tim Robbins, ‘Mystic River’ (2004)
Robbins gave one of his most nuanced performances as a Boston man forever haunted by a childhood trauma in Clint Eastwood’s somber neo-noir mystery. Decades after being sexually abused, his erratic actions cause tension among friends and family, and he becomes the prime suspect in the murder of a pal’s daughter.
13. Troy Kotsur, ‘CODA’ (2022)
In the endearing best-picture winner, he’s the salty deaf father of a hearing teen girl (Emilia Jones) whose interest in exploring singing takes her away from the family fishing business. Kotsur brings such warmth and joy to the screen, especially in a tear-jerking scene where his character has his world opened up by experiencing, in his own way, the kid’s musical gift.
12. Jared Leto, ‘Dallas Buyers Club’ (2014)
Jared Leto is a sucker for a transformational part, and he pulled off something special in the heartbreaking true-life drug drama. While Matthew McConaughey plays the real figure of Ron Woodroof, Leto turns in a touching portrayal of a trans woman faced with AIDs yet never losing her verve as the fictional Rayon.
11. Kieran Culkin, ‘A Real Pain’ (2025)
In writer/director Jesse Eisenberg’s comedy, Culkin and Eisenberg play estranged cousins who embark on a trip to Poland to explore their Jewish roots. As the more mercurial of the two, Culkin masterfully navigates an excellent character arc, taking an outspoken nuisance and giving him thoughtful nuance on a Holocaust tour.
10. Christopher Plummer, ‘Beginners’ (2012)
Mike Mills’ tale of fathers, sons and generational romance features the legendary Plummer in one of his later roles. It’s also one of his essential ones, as a father who comes out as a gay man during his twilight years and faces a cancer diagnosis with honesty and dignity, all while being an inspiration for his son (Ewan McGregor).
9. Robert Downey Jr., ‘Oppenheimer’ (2024)
Hollywood’s erstwhile Iron Man can do dastardly when the opportunity arises. Downey deliciously goes for petty, vindictive and nasty as Lewis Strauss, a political foe wanting to tear down Cillian Murphy’s J. Robert Oppenheimer not for America’s benefit or national security but because of a perceived personal slight.
8. Daniel Kaluuya, ‘Judas and the Black Messiah’ (2021)
Kaluuya superbly inhabits the role of a stirring, profound orator, playing Black Panther Party leader Fred Hampton in the 1960s-set period thriller. As the FBI works to silence popular political dissent, Kaluuya projects appealing charisma in his speech scenes as well as a deep well of emotion as the gravity of Hampton’s work weighs heavily.
7. Alan Arkin, ‘Little Miss Sunshine’ (2007)
May everyone have a loved one as eccentric and caring as Arkin’s patriarch. A dysfunctional family goes on a road trip of misadventure to take a little girl (Abigail Breslin) to a child beauty pageant, and Arkin plays the rascally grandpa who instills in her and others the power of trying and being one’s true self.
6. Javier Bardem, ‘No Country for Old Men’ (2008)
May everyone avoid anybody this downright creepy. And don’t let the Dorothy Hamill haircut fool you. Like the Terminator but flesh and bone, Bardem is oh-so-chilling as psychopathic hitman Anton Chigurh, who’s doggedly efficient when it comes to finishing a task and leaves the fate of victims to the whims of a coin flip.
5. Christoph Waltz, ‘Inglourious Basterds’ (2010)
No one does gleefully evil better. Quentin Tarantino’s ultraviolent World War II fantasy gave the Austrian-German actor his villainous breakout role as Hans Landa, a Nazi baddie with an upper-crust cultural side. Waltz lends a slimy charisma to the merciless SS colonel, who gets a satisfying comeuppance via carving knife.
4. Brad Pitt, ‘Once Upon a Time in Hollywood’ (2020)
In Quentin Tarantino’s alt-history fable, Pitt plays a steely stunt double equally adept at fixing TV antennas or dealing with the Manson Family, all with a grin on his weathered face. Yet the star hints at a darkness underneath the suntanned exterior that adds so many more layers to a seemingly superficial personality.
3. Mahershala Ali, ‘Moonlight’ (2017)
Barry Jenkins’ stunning movie explores the maturation of a gay black man from lost child to bullied teenager to intimidating drug dealer. Ali beautifully cements the film’s strong sense of empathy early on as a crack pusher who tries to give the main character a loving foundation even as he’s indirectly responsible for the kid’s adversity.
2. J.K. Simmons, ‘Whiplash’ (2015)
How much of a master thespian do you have to be to turn a jazz band director into a menacing supervillain? Wielding a baton and supreme intensity, Simmons makes a drumming Miles Teller’s life a living hell in Damien Chazelle’s amazingly stressful, psychologically taxing (in a good way!) musical drama.
1. Heath Ledger, ‘The Dark Knight’ (2009)
The greatest screen villain of this century, period, cut the blockbuster check. Ledger ingeniously plays the Joker as a chaotic force of nature, a scarred and unknowable ghoul clad in clown paint and a garish suit from Demon’s Wearhouse. While Christian Bale’s Batman is the hero we need, Ledger is the magnetic figure we can’t stop watching – an uber-anarchist so incomparably charming that it’s impossible not to root for him on some deep, dark level.
This article originally appeared on USA TODAY: Best supporting actor winners ranked in Oscar history: List
