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A couple laughing in a photo booth in this photo from Paramount Pictures.
Multi-Oscar winners Meryl Streep and Robert De Niro star in the 1984 film “Falling in Love.” (Image: Paramount Pictures)

With the Academy Awards approaching, there’s a lot of talk about the potential winners. Receiving an Oscar is the highest honor in Hollywood, one that many actors only dream of after long and successful careers. Winners are selected by the Academy, which consists of specially selected, seasoned actors with at least three scripted roles, among other requirements.

As you can imagine, the system includes an element of an “old boys club,” where certain films and actors with specific appeal to Academy members win the popularity contest. What may surprise you is how difficult it is for an actor to get an Oscar at all. Film studios spend big money on campaigns to get the Academy’s attention, and actors have a long tradition of wining and dining Academy members, yet only seven actors in history have ever received more than two awards.

Forty-four actors in total have won at least two Academy Awards. This list will talk about all of the most awarded winners, as well as a selection of popular winners with two accolades. A couple of decorated actors on the list are nominated for another Oscar in the upcoming 2024 ceremony, which could mean new additions to the triple winners this year.

Katharine Hepburn (4)

A woman swimming in this photo from Romulus Films.
History’s top Oscar winner is Katharine Hepburn. (Image: Romulus Films)

Katharine Hepburn was an icon of Hollywood’s Golden Age, known for her fierce independence and exceptional charisma. Her career spanned seven decades, defying expectations with each groundbreaking role. Whether fighting the societal taboo of divorce in “The Philadelphia Story” or contributing to normalizing interracial marriage in “Guess Who’s Coming to Dinner,” Hepburn embodied strength, wit, and unwavering individuality.

With a record-breaking four Oscars, she remains the most decorated actor in Academy Award history. She won her first Oscar for “Morning Glory,” followed by awards for “Guess Who’s Coming to Dinner,” “The Lion in Winter,” and “On Golden Pond.” Hepburn was a trailblazer for women in film, inspiring other actresses who appear on this list. While she may have had some advantages with a smaller Academy and fewer annual films released in her time, she has held her record for four decades, proving that she’s still untouchable.

Daniel Day-Lewis (3)

Abraham Lincoln at a rainy battle camp in this photo from DreamWorks Pictures.
Daniel Day-Lewis won an Oscar for his role as Abraham Lincoln in “Lincoln.” (Image: DreamWorks Pictures)

Daniel Day-Lewis’ acting prowess over his long on-and-off career has made him the most decorated male actor in Oscars history. A method actor, he’s known for his meticulous preparation and immersive approach to roles. He’s a master impersonator, portraying historical figures like Abraham Lincoln, and artistic geniuses like Christy Brown in “My Left Foot.”

He earned his first Oscar for “My Left Foot” and his second in 2007 for “There Will be Blood,” but he truly became a household name when he won for playing the iconic president in “Lincoln.” His unmatched three Academy Awards for Best Actor would make him, according to the Academy, the best actor in history. Whether or not you agree may come down to how much stock you hold in critical consensus, but despite flaws in the system, we can’t take away from Daniel Day-Lewis’ achievements. He’s clearly one of the best actors of our time, and may yet be remembered among the halls of fame of cinematic legends.

Frances McDormand (3)

A woman looks troubled sitting next to a field in this photo from Blueprint Pictures.
Frances McDormand is a tour de force, evidenced by her three Oscars. (Image: Blueprint Pictures)

Hollywood’s dark horse, Frances McDormand, favors roles with an indie slant and hard-hitting emotional impact. She has never gone for major Hollywood stardom, choosing her projects carefully and approaching them as an artist truly devoted to her craft. She takes a fearless approach to roles, inhabiting complex characters with a magnetic presence that audiences can’t look away from.

She often portrays resilient women in films, as she did for her Oscar-winning roles in “Fargo” and “Three Billboards Outside Ebbing, Missouri.” She has also gained a reputation for nuanced character studies that capture the essence of humanity, like her most recent win for “Nomadland.” It’s great to see an actress with so many wins who refuses to lean on sex appeal or jump at the biggest-budget films. It proves that humble dedication and pure talent can still be rewarded in a flashy environment like the film industry.

Walter Brennan (3)

A hillbilly man holding a harmonica in a saloon in this photo from Armada Productions.
Legendary character actor Walter Brennan is among the top Oscar winners of all time. (Image: Armada Productions)

You may not have heard of Walter Brennan, but in the days of classic Hollywood, he was known as the greatest character actor of his time. The only actor to have won three Best Supporting Actor awards, he shows that you don’t have to be the leading man to leave your mark on a film. Stuck in a rut as an uncredited extra throughout his early career, Brennan was filming a fight scene in 1932 when all his teeth were accidentally kicked out, forcing him to wear dentures. He later said this was the luckiest break he ever got because his ability to remove his dentures landed him a series of old-man roles.

Known for his distinctive voice and his memorable roles in Westerns and silver screen classics, he often played rugged but endearing characters, like the wise and weathered old-timer in “To Have and Have Not” and the cantankerous yet lovable sidekick in “Rio Bravo.” His three Academy Awards for Best Supporting Actor were won for his roles in “Come and Get It,” “Kentucky,” and “The Westerner.” It may seem strange, and perhaps another quirk of the system, that Brennan remains one of the most decorated actors in Oscar history, but it’s also great to see supporting actors celebrated for their contributions to film.

Ingrid Bergman (3)

A man comforts a distressed woman in a lavish sitting room in this photo from Metro-Goldwyn-Mayer.
Ingrid Bergman’s Oscar-winning role in “Gaslight” introduced the concept of gaslighting to the popular lexicon. (Image: Metro-Goldwyn-Mayer)

Silver screen sweetheart Ingrid Bergman was roundly applauded in her time for her grace, beauty, and unparalleled talent. During her illustrious five-decade career, she took on a wide range of characters with remarkable depth and authenticity. She chose a natural, understated approach that avoided theatrical gestures and melodrama that was the norm of the silent film era and early talkies, setting her apart as part of a new era of movie stars. She relied on her expressive eyes and voice to convey complex emotions that created captivating performances, like her timeless portrayal of Ilsa Lund in “Casablanca” and her moving performance as Sister Mary Benedict in “The Bells of St. Mary’s.” She took home three Academy Awards for acting, two for Best Actress in “Gaslight” and “Anastasia,” and one for Best Supporting Actress in “Murder on the Orient Express.”

Jack Nicholson (3)

A man in a mental facility has a sly smile in this photo from Fantasy Films.
Jack Nicholson has played many iconic roles. (Image: Fantasy Films)

Born to parents in showbiz, Jack Nicholson was meant to be an actor — and a great one, at that. His big break came in 1969 when he starred in the independent road drama “Easy Rider,” which launched him into mainstream roles, and his career eventually became one of widespread acclaim and adoration. When you think of his performances, you might picture the intensity of his manic eyes in “The Shining.” Along with his raspy voice and unpredictable delivery, his eyes give him the ability to convey extreme, chilling emotion. He’s known for projects with dark, twisted humor, including collaborations with Michelangelo Antonioni, Robert De Niro, and Stanley Kubrick. His most famous films showcase his ability to balance intense emotional drama with brilliant comic timing. Nicholson has won three Oscars, two for Best Actor in “One Flew Over the Cuckoo’s Nest” and “As Good as It Gets,” and one for Best Supporting Actor in “Terms of Endearment.”

Meryl Streep (3)

A pair of politicians raise their clasped hands on stage in this photo from DJ Films.
Meryl Streep should’ve received twice as many Oscars, in my opinion. (Image: DJ Films)

When you think of great actors of our time, Meryl Streep may be one of the first to come to mind. Her long career on the stage and screen has earned her universal acclaim and made her one of the highest-paid and most in-demand actresses in the business. She dedicates deep research and planning to her roles and has been described as chameleon-like, creating distinct accents, voices, posture, gait, and facial expressions for each of her characters. She has taken on diverse projects, from cult classics like “The Devil Wears Prada” and “The Hours” to blockbusters like “Mamma Mia!” and “Julie & Julia.” She has won two Oscars for Best Actress, for her roles as a concentration camp survivor in “Sophie’s Choice” and as divisive British Prime Minister Margaret Thatcher in “The Iron Lady.” She won her first Oscar back in 1979 for Best Supporting Actress for her role as a conflicted divorcee in “Kramer vs. Kramer.”

Robert De Niro (2)

A man in glasses and a cowboy hat in this photo from Apple Studios.
Robert De Niro has been nominated in the upcoming ceremony for Best Supporting Actor in “Killers of the Flower Moon.” (Image: Apple Studios)

Although he starred in crime films throughout the late ’60s and early ’70s, Robert De Niro hit the A-List when he was cast as Vito Corleone in “The Godfather Part II,” a young version of Marlon Brando’s iconic character. Also a method actor, de Niro is known for playing gritty, intense roles and taking on the mannerisms and physicality of his characters. He famously gained weight for “Raging Bull” and learned a Sicilian dialect for “The Godfather Part II.” Despite his tough guy persona and long history of crime film collaborations with director Martin Scorsese, de Niro shows surprising range, such as his portrayal of a mentally unstable Vietnam veteran in “Taxi Driver” and a humorously menacing obsessive stalker in “Rupert Pupkin in The King of Comedy.” He has won two Academy Awards, one for Best Actor in “Raging Bull” and one for Best Supporting Actor in “The Godfather Part II.” The 80-year-old actor is currently nominated for Best Supporting Actor for “Killers of the Flower Moon” at the upcoming 96th Academy Awards.

Cate Blanchett (2)

A woman looks out of a window while drinking in this photo from Gravier Productions.
Cate Blanchett took home a Best Actress for her role in “Blue Jasmine.” (Image: Gravier Productions)

Most of us first experienced Cate Blanchett’s commanding presence as the wise and prophetic elf queen, Galadriel, in “The Lord of the Rings” film trilogy in the early 2000s. It was immediately clear, however, that the Australian beauty was no ordinary actress. Her voice control and finely-tuned facial expressions make her a master of technical screen acting that film students in the future will likely study. She portrayed Katharine Hepburn in “The Aviator,” as well as other historical figures like Queen Elizabeth I in “Elizabeth” and “Elizabeth: The Golden Age,” using method acting to fully become her roles. She has won two Academy Awards, one for Best Supporting Actress for her role as Hepburn in “The Aviator,” and one for Best Actress as a fallen socialite struggling with mental illness in the Woody Allen-directed film “Blue Jasmine.”

Tom Hanks (2)

A man in the hospital eats two ice cream cones in this photo from Paramount Pictures.
Tom Hanks’ role in “Forrest Gump” has become an unforgettable part of pop culture. (Image: Paramount Pictures)

Tom Hanks’ accomplished career on stage and screen includes both commercially popular movies and highbrow productions. His natural charm and sincerity make him a favorite to play relatable and believable everyman characters. Most of us know him best from his portrayal of a clueless but fearless and lovable mentally disabled character in “Forrest Gump,” a role which showcased his incredible physical acting skills. His work ranges from physically rugged roles like a man stranded on a deserted island in “Cast Away” and an astronaut in crisis in “Apollo 13,” to memorable voice acting as Woody in the “Toy Story” films. Hanks won his first Oscar for his role in “Philadelphia,” playing a gay lawyer with AIDS who sues his firm for discrimination, at a time when playing gay characters could be career suicide. He went on to win a second Best Actor Oscar the following year for “Forrest Gump.” Hanks has been nominated a total of six times, most recently as Best Supporting Actor for “A Beautiful Day in the Neighborhood,” and may well add another statuette to his shelf before his career is done.

Maggie Smith (2)

A man looks at a woman staring into the distance in this photo from Twentieth Century-Fox Productions.
Before she was Professor McGonagall in the “Harry Potter” film franchise, Maggie Smith won Best Actress for “The Prime of Miss Jean Brodie.” (Image: Twentieth Century-Fox Productions)

We can all imagine Maggie Smith’s stern face in a witch’s hat, looking down at us from the head of a Transfiguration classroom, but before she took on the iconic role of Professor McGonagall in the “Harry Potter” film series, she had a highly-respected career as far back as the ’60s. A master of perfectly timed delivery, she leverages her stern British image with dry wit and sarcasm, making her one of the most subtly funny actresses of all time. She’s not afraid to play with and break stereotypes, adapting to new generations of film and television that keep her working at age 89. Arguably the best and most iconic role of her career was as Violet Crawley, the highly judgmental and razor-sharp Dowager Countess of Grantham in “Downton Abbey.” While her television roles can’t be considered for the Oscars, her near-perfect performance proves she has only improved with age. She has won two Academy Awards for Best Actress, one for her role as an unrestrained teacher at a girls’ school in “The Prime of Miss Jean Brodie” and, ironically, one for playing a first-time Best Supporting Actress Oscar winner in “California Suite.”

Mahershala Ali (2)

A man in a lavish traditional dress sits on a decorated chair in this photo from Participant.
Mahershala Ali is the first Black actor to win multiple Oscars and has become one of the most in-demand faces in Hollywood. (Image: Participant)

Mahershala Ali is only one of two Black actors to ever receive more than one Oscar (the other being Denzel Washington), making it hard not to see what a terrible snub this is to the likes of Sidney Portier and Morgan Freeman. Ali is both a rising star and an established actor, occupying this list with some of the greatest performers in cinema history. He has had the advantage of taking on some incredibly powerful roles in his relatively short career, such as the drug dealer turned wise mentor in “Moonlight” and the unjustly overlooked Black classical pianist Don Shirley in “Green Book,” taking home a Best Supporting Actor statuette for each film. He has also further established himself as a critically acclaimed actor through his TV roles, such as the unsettling hit man Remy Danton in “Fargo” and the menacing villain Cottonmouth in Marvel’s “Luke Cage.” We’ll certainly see more incredible things from him as his career progresses, and perhaps he’ll even become the first Black triple-Oscar winner one day.

Jodie Foster (2)

A woman sits in a chair shuffling cards in this photo from Black Bear.
Jodie Foster is up for another Oscar for Best Supporting Actress in “Nyad.” (Image: Black Bear)

Jodie Foster has been celebrated for her talented and versatile performances since the ’70s. She played opposite Robert De Niro in the classic “Taxi Driver,” catapulting her to fame and landing her a starring role in “Freaky Friday” that same year. Known for her naturalism, intelligence, and her underplaying of characters, she’s highly relatable in her performances. But despite her girl-next-door mannerisms, her most famous roles have demanded sustained emotional intensity. Her most iconic role, of course, was as Clarice Starling, the FBI trainee interviewing the cannibalistic serial killer Hannibal Lecter in “The Silence of the Lambs,” a role for which she won Best Actress. Her first Oscar, however, was for playing a resilient victim prosecuting a brutal gang rape in “The Accused.” In the past year, she took on a starring role in the police anthology drama, “True Detective: Night Country,” and is currently nominated for Best Supporting Actress in the upcoming Oscars for “Nyad.”

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