Every Actor Who Won an Oscar for Playing a Real-Life Performer

The Academy Awards are Hollywood’s ultimate celebration. Presented by the Academy of Motion Pictures Arts and Sciences and rewarding the best performances from any given year, the Oscars are the most coveted award in the business. Many of cinema’s most iconic performers have won the statuette since the first ceremony in 1927, cementing their place in the annals of cinematic history.



The Oscars love a good real-life story, with 21 biopics winning Best Picture. However, entertainment stories are rare in the Oscars’ history, with only a few actors winning Oscars for playing figures of the stage and screen. From stage performers to popular musicians and silver screen icons, these real-life entertainers led huge and impressive lives, providing the basis for compelling films and, as it turns out, Oscar-winning portrayals.

12 Luise Rainer – Best Actress 1937

For Playing Anna Held in ‘The Great Ziegfeld’ (1936)

Image via Loew’s Inc.

Luise Rainer is among the few performers to have two Best Actress Oscars—unfortunately, it’s for two films that have aged quite poorly. Her first win came for playing Anna Held, a Polish-French Broadway stage performer in the 1936 musical drama The Great Ziegfeld. The film depicts the rise of Broadway producer Florenz Ziegfeld, whose lavish productions would eventually become the Ziegfeld Follies.

The film also depicts Ziegfeld’s love triangle with Held and fellow actress Billie Burke, played by Myrna Loy. Rainer is quite good in Ziegfeld, effortlessly fitting with the production’s excess and standing out without necessarily pulling focus. Alas, the film itself has aged quite badly, to the point where it’s now considered among the worst Best Picture winners.

The Great Ziegfeld Film Poster

The Great Ziegfeld
Release Date
September 23, 1936

Robert Z. Leonard

William Powell , Myrna Loy , Luise Rainer , Frank Morgan

176 minutes

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11 James Cagney – Best Actor 1943

For Playing George M. Cohan in ‘Yankee Doodle Dandy’ (1942)

James Cagney as George M. Cohan smiling at the camera in Yankee Doodle Dandy
Image via Warner Bros.

The iconic James Cagney might be best known for his gangster roles in classics like White Heat and The Public Enemy, but he won his Oscar for playing against type in the 1942 musical biopic Yankee Doodle Dandy. The film chronicles the career of actor, producer, writer, and director George M. Cohan, who could come to be regarded as « The Man Who Owned Broadway. »

Yankee Doodle Dandy is a fantastic and delightful project. Although its shameless brand of patriotism might seem slightly outdated today, it’s easy to understand why voters fell under Cagney’s spell. For a guy best known for playing ruthless criminals to disappear so wonderfully in the role of a pure entertainer is a tremendous acting feat. Today, Yankee Doodle Dandy remains highly regarded, as is Cagney’s performance, his only Oscar-winning turn.

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10 Barbra Streisand – Best Actress 1969

For Playing Fanny Brice in ‘Funny Girl’ (1968)

Barbra Streisand as Fanny Brice performing on stage with dancers in 'Funny Girl'
Image via Columbia Pictures

Hello, gorgeous, indeed. Barbra Streisand won her Oscar for her explosive portrayal of Fanny Brice in the hit musical Funny Girl. The film tells Brice’s story as an immensely talented performer who soon becomes a star on the stage. Things change when she falls for the dashing entrepreneur and gambler Nicky Arnestein, played by Omar Shariff.

Streisand is outstanding as Brice, delivering a tour-de-force enhanced by her booming voice belting out hits like « Don’t Rain on My Parade » and « My Man. » Funny Girl was a major hit and earned Streisand rave reviews. In an unprecedented race, Streisand tied with Katharine Hepburn for Best Actress, the only time in Academy history that this has happened. Streisand’s Oscar is fondly remembered today, with many considering her among the all-time best winners in the category.

funny girl poster

Funny Girl
Release Date
September 18, 1968

William Wyler

2 hr 29 min

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9 Sissy Spacek – Best Actress 1981

For Playing Loretta Lynn in ‘Coal Miner’s Daughter’ (1980)

Loretta Lynn singing on stage in Coal Miner's Daughter - 1980
Image via Universal Pictures

Four years after her Oscar-nominated breakout role in Brian De Palma‘s Carrie, Sissy Spacek won the coveted statuette for her take on country music singer Loretta Lynn in the film Coal Miner’s Daughter. The film chronicles Lynn’s early life in poverty, her marriage at 15, and her eventual success as one of the most acclaimed country singers of the 20th century’s second half.

One of the best movies about country music, Coal Miner’s Daughter is a riveting portrayal of overcoming hardship. Spacek was an unlikely choice to play Lynn but proved the naysayers wrong, delivering a complex and compelling performance that revealed new sides of an icon who many people thought they knew. Coal Miner’s Daughter was a before and after in celebrity biopics, thanks to its humane and earnest approach, greatly enhanced by Spacek’s Oscar-winning turn.

Coal Miner’s Daughter
Release Date
March 7, 1980

Michael Apted


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8 Martin Landau – Best Supporting Actor 1995

For Playing Bela Lugosi in ‘Ed Wood’ (1994)

Béla Lugosi sitting on a couch in Ed Wood
Image via Walt Disney Studios Motion Pictures

Ed Wood is among the most infamous directors in Hollywood history, an influential figure in the rise of cult cinema. His life is the basis for Tim Burton‘s wacky biopic Ed Wood, which depicts his most prolific time as a leading behind-the-scenes force in B-horror movies. His relationship with horror icon Bela Lugosi, played by Martin Landau, also plays a crucial role in the story.

Thanks to Burton’s trademark offbeat style, Ed Wood is a worthy examination and celebration of Wood’s oeuvre and legacy. Landau is simply incredible as Lugosi, finding the perfect balance between the film’s overt absurdism, Lugosi’s well-known flair, and the story’s touching emotional core. The result is a tender performance that is as much a love letter to Lugosi as a vibrant ode to his on-screen persona. Many might think Samuel L. Jackson‘s dynamo performance in Pulp Fiction might’ve been more deserving of the Oscars, but Landau is a worthy and inspired winner in the category.

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7 Cate Blanchett – Best Supporting Actress 2005

For Playing Katharine Hepburn in ‘The Aviator’ (2004)

Jude Law as Errol Flynn kissing Cate Blanchett as Katherine Hepburn's hand at a party in The Aviator
Image via Warner Bros.

Cate Blanchett is among her generation’s finest actresses. Already an Oscar nominee for her work in 1998’s Elizabeth, Blancett joined forces with Martin Scorsese for the 2004 biopic The Aviator, a dramatization of the life of pilot, magnate, and producer Howard Hughes. Blancett plays the iconic Katharine Hepburn, who had a romantic relationship with Hughes in the mid-1930s.

Although The Aviator is all about Leonardo DiCaprio, it was Blanchett who won the Oscar for her assertive take on Hepburn. Playing such a larger-than-life person must’ve been daunting, but Blanchett captures Hepburn’s well-known mannerisms and speech to a tee. The performance is more imitation than evocation, but Blanchett never cheapens it, maintaining a firm grasp on Hepburn and delivering a compelling, if somewhat surface, depiction of a Hollywood legend.

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6 Jamie Foxx – Best Actor 2005

For Playing Ray Charles in ‘Ray’

Ray Charles singing into a microphone in the Film Ray
Image via Universal Pictures

Another actor won the Oscar for playing a real-life performer at the 2005 ceremony. DiCaprio lost the Oscar to Jamie Foxx‘s depiction of influential songwriter and pianist Ray Charles in the biopic Ray. Directed by Taylor Hackford. Ray chronicles 30 years in the life of the celebrated soul singer, dealing with his substance abuse and struggles while on his way to the top.

Ray soars on the strength of Foxx’s performance. The actor loses himself in the role, bringing Charles to life with impressive faithfulness and striking commitment. It’s a tremendous performance, supported by an impressive ensemble and Hackford’s dynamic performance. Ray lives up to Charles’ rich legacy without softening any of the blows, producing one of the most impactful biopics of the 21st century.

Release Date
October 29, 2004


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5 Reese Witherspoon – Best Actress 2006

For Playing June Carter Cash in ‘Walk the Line’ (2005)

June Carter standing next to Johnny Cash on stage singing together in Walk the Line
Image Via 20th Century Fox

America’s sweetheart Reese Witherspoon won the Best Actress Oscar for playing June Carter Cash in James Mangold‘s musical biopic Walk the Line. Joaquin Phoenix stars as Johnny Cash, the legendary country singer, with the film depicting his long struggle with substance abuse and his tumultuous romance with June Carter.

Walk the Line portrays Cash’s life with a loving yet decidedly Hollywood-y approach. However, the film finds its greatest strength in the chemistry between Phoenix and Witherspoon, who bring the Carters’ timeless romance to life with honesty and passion. As Carter, Witherspoon is an endless fountain of effervescence, injecting the film with some much-needed warmth. Her Oscar win remains somewhat divisive today, but her loving, firm performance is certainly worthy.

Walk the Line movie poster featuring Joaquin Phoenix and Reese Witherspoon

Walk The Line
Release Date
September 13, 2005


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4 Marion Cotillard – Best Actress 2008

For Playing Édith Piaf in ‘La Vie en Rose’ (2007)

Edith Piaf (Marion Cotillard) sings into a microphone on stage while wearing a black dress and a cross necklace.
Image via Icon Film Distribution

French icon Édith Piaf comes to live with Marion Cotillard‘s stunning performance in Olivier Dahan‘s 2007 musical biopic La Vie en Rose. The film follows Piaf’s turbulent life, including her childhood in poverty, her subsequent success, and her many personal tragedies and drug addiction. Gérard Depardieu co-stars as Louis Leplée, the nightclub owner who discovered Piaf.

It’s not an overstatement to say Cotillard delivers one of the all-time great female performances in La Vie en Rose. The actress is utterly devastating as Piaf, capturing the singer’s tragedies with remarkable and heart-wrenching sincerity, to the point where some scenes become near-unbearable to watch. Like the real Piaf, Cotillard finds the right balance between theatricality and sincerity, earning a richly deserved Oscar as a reward.

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3 Mahershala Ali – Best Supporting Actor 2019

For Playing Don Shirley in ‘Green Book’ (2018)

Close-up of Doctor Donaled Shirley, sitting seriously in the back of a car in Green Book
Image via Universal Studios

Over a decade passed before another performer won an Oscar for playing a real-life performer. In 2019, Mahershala Ali won his second Best Supporting Actor Oscar for his work in the 2018 film Green Brook, playing pianist and performer Don Shirley. The film centers on Shirley’s friendship with his driver and bodyguard, Frank Vallelonga.

Green Book is a questionable depiction of race relations, and its Best Picture win remains highly divisive, with many considering it the worst of the 2010s. However, Ali is among Green Book‘s few redeeming factors. The actor gives a soulful, thoughtful performance that goes a long way to soften the film’s rougher edges, especially those concerning racial stereotypes. Although the story is still uneven at best and questionable at worst, Ali’s work in Green Book is noteworthy.

Green Book
Release Date
November 16, 2018

Peter Farrelly


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2 Rami Malek – Best Actor 2019

For Playing Freddie Mercury in ‘Bohemian Rhapsody’ (2018)

Freddie Mercury during a concert in 2018's 'Bohemian Rhapsody'
Image via 20th Century Studios

Rami Malek won the 2019 Oscar for Best Actor, proving that 2018 was truly a cursed year. The actor gives a bizarre performance in the musical biopic Bohemian Rhapsody, which sees him playing Freddie Mercury, the legendary frontman of the band Queen. The film chronicles roughly a fifteen-year period, from the band’s formation in 1970 to their now-iconic concert at Wembley Stadium.

Bohemian Rhapsody is not a great movie, and Malek gives a suitably not great performance. Falling straight into the imitation category, Malek stumbles through a weak screenplay, doing little to elevate it. Mercury’s real-life persona completely overwhelms him, and the actor settles for doing a pale impression of it. Less than a decade after the win, Malek’s Oscar has aged like milk, to the point where many consider him among the all-time worst Best Actor winners. By the looks of it, its dubious reputation shows no sign of improving in the near future.

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1 Renée Zellweger – Best Actress 2020

For Playing Judy Garland in ‘Judy’ (2019)

Judy Garland singing on stage in Judy.
Image via 20th Century Studios

And speaking of Oscar wins that haven’t aged well, let’s talk about Renée Zellweger. Already an Oscar winner for Best Supporting Actress, Zellweger won a second trophy for playing the iconic Judy Garland in the 2019 biopic Judy. The film chronicles the last year of Garland’s career, with flashbacks to her time filming The Wizard of Oz.

Zellweger tries her best, but she never quite captures Garland’s particular essence. She delivers a safe performance that settles for capturing Garland’s distinctive traits without ever attempting to go deeper and revealing a new side to the larger-than-life diva. Judy isn’t a bad film, and Zellweger’s work is good enough to earn the recognition it did. Whether it’s Oscar-worthy, however, remains a matter of intense debate.

Release Date
September 27, 2019

Rupert Goold


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NEXT: 10 Actors Who Made Oscars History

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