Best Supporting Actor Oscar: Ranking the Greatest Winners of the 21st Century
The Best Supporting Actor Oscar is one of the most celebrated accolades at the Academy Awards, recognizing some of the most compelling performances in cinematic history. Over the past 25 years, this category has honored a mix of unforgettable characters, from terrifying villains to inspiring mentors. Whether it’s a chilling antagonist, a troubled soul, or a comedic yet heartfelt role, these performances have left an indelible mark on audiences worldwide.
As we approach the 2025 Academy Awards, with Kieran Culkin expected to join this elite club, we take a deep dive into the Best Supporting Actor Oscar winners of the 21st century, ranking them from 25 to 1 based on their impact, artistry, and sheer brilliance.
Quentin Tarantino’s Western revenge thriller features Waltz as King Schultz, a bounty hunter who teams up with Django (Jamie Foxx) in a quest to free his wife. Waltz delivers a unique and charismatic performance, adding depth to an unconventional mentor role.
In this meta dramedy, Cooper plays a quirky horticulturist caught in an unpredictable plot. His over-the-top portrayal of John Laroche adds comic relief and tension in equal measure, making his Oscar-winning performance unforgettable.
Playing the devoted husband of a woman struggling with Alzheimer’s, Broadbent gives a heartbreaking performance in this poignant drama, showing the devastating effects of dementia on a loving relationship.
A gym assistant and former boxer, Freeman plays Scrap, a wise mentor who helps guide Maggie (Hilary Swank) and coach Frankie (Clint Eastwood) in a story that transcends the sports drama genre.
Del Toro shines as a conflicted Mexican police officer in Steven Soderbergh’s gritty crime drama, providing a nuanced portrayal of morality amid the war on drugs.
Bale’s portrayal of Dicky, a washed-up boxer turned crack addict, is raw and electrifying, showcasing his transformation skills and dedication to bringing real-life struggles to the screen.
In this geopolitical thriller, Clooney immerses himself into the role of a disillusioned CIA operative, adding complexity and realism to the film’s high-stakes narrative.
Rylance delivers a subtle yet powerful performance as a Soviet spy in Steven Spielberg’s Cold War thriller, making his presence felt despite the film being centered on Tom Hanks’ character.
As a compassionate doctor running an orphanage, Caine’s role exudes warmth and wisdom, adding emotional depth to this literary adaptation.
In a genre-bending film, Quan plays multiple versions of Waymond Wang, bringing humor, heart, and action-packed sequences to his standout comeback performance.
Ali’s portrayal of pianist Don Shirley adds layers to this controversial yet engaging film, presenting a refined yet troubled artist navigating racial tensions in 1960s America.
In Clint Eastwood’s neo-noir mystery, Robbins gives a haunting performance as a man struggling with past trauma, making his character one of the film’s most tragic figures.
As the loving yet tough father in a deaf family, Kotsur brings warmth and humor to his role, especially in a tear-jerking scene where he connects with his daughter’s musical dreams.
Leto’s performance as Rayon, a trans woman battling AIDS, is both heartbreaking and inspiring, showcasing his dedication to transformational acting.
Plummer’s role as an elderly man coming out as gay late in life is both tender and powerful, earning him a well-deserved Best Supporting Actor Oscar.
Downey Jr. steps away from his Marvel persona to portray a ruthless politician, delivering a career-defining performance in Christopher Nolan’s epic.
Kaluuya’s portrayal of Black Panther Party leader Fred Hampton is commanding, making his presence felt through impassioned speeches and emotional depth.
Arkin’s role as a lovable but foul-mouthed grandpa adds humor and wisdom to this indie classic, making him a standout in a stellar ensemble cast.
Bardem’s chilling portrayal of hitman Anton Chigurh remains one of the most terrifying villainous performances in modern cinema.
Waltz’s Nazi Colonel Hans Landa is both charming and sinister, making his character one of Tarantino’s most memorable creations.
Pitt brings charisma and complexity to Cliff Booth, a laid-back yet dangerous stunt double, earning his long-overdue Best Supporting Actor Oscar.
Ali’s portrayal of Juan, a drug dealer who becomes a surrogate father figure, adds layers of warmth and tragedy to this beautifully crafted coming-of-age film.
Simmons transforms a jazz instructor into a terrifying, relentless force, creating one of the most intense teacher-student dynamics ever seen on screen.
Ledger’s Joker remains unparalleled, delivering a performance that redefined what a superhero movie villain could be. His posthumous Best Supporting Actor Oscar win was a testament to his legacy.
