Getty Images, UIP

Sunday's episode of Last Week Tonight delivered a scathing segment on Hollywood whitewashing: the movie industry's tone-deaf insistence on casting white actors as people of color, often to utterly disastrous effect.

Think Emma Stone in Aloha, Jake Gyllenhaal in Prince of Persia, and the main characters in 21—or think Laurence Olivier in Othello, Marlon Brando in Viva Zapata!, Katharine Hepburn in Dragon Seed, and, most notoriously, Mickey Rooney in Breakfast at Tiffany's.

Marlon Brando in 'Viva Zapata,' Katharine Hepburn in 'Dragon Seed,' and Laurence Olivier in 'Othello.'
Twentieth Century Fox, MGM, Warner Bros.

As this weekend's 88th Academy Awards ceremony draws nearer, here's a closer look at six white actors who won Oscars for playing characters with racial and ethnic backgrounds very different from their own. (For an expansive survey of "racebending" nominees as well as winners, check out this rundown.)

Luise Rainer as O-Lan in The Good Earth (1937)

IMDb, MGM

The German-born actress won her second consecutive Best Actress Oscar for playing a Chinese peasant woman in this adaptation of Pearl S. Buck's 1931 novel. Buck pushed to cast the film with actors of Asian descent, but once white actor Paul Muni was chosen for the lead role, Wang Lung, it was essentially a foregone conclusion that a white actress would play his wife—the on-screen depiction of interracial relationships was forbidden by the Motion Picture Production Code.

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Although MGM refused to cast Chinese-American star Anna May Wong as O-Lan, the studio invited her to play Lotus, the concubine who becomes Wang Lung's second wife. She declined, explaining, "…you're asking me—with Chinese blood—to do the only unsympathetic role in the picture, featuring an all-American cast portraying Chinese characters." (The Austrian-born Tilly Losch would play Lotus instead.)

Ironically, the "facial inlays" used by makeup artist Jack Dawn to transform Rainer, Muni, and other European actors into yellowface would be praised for their apparent authenticity.

Hugh Griffith as Sheik Ilderim in Ben-Hur (1959)

IMDb/Loew's

The Welsh actor won Best Supporting Actor for his role as the wealthy, burpy Arab man who invites Charlton Heston's title character to join a chariot race. In one scene in the Best Picture-winning film, the "lusty" sheik tells Judah Ben-Hur, "One wife? One god I can understand, but one wife? That is not civilized. It is not generous."

George Chakiris as Bernardo in West Side Story (1961)

Left: Chakiris with Rita Moreno at the 34th Academy Awards.
Getty Images, United Artists

The Greek-American actor and dancer won Best Supporting Actor for playing the leader of the Sharks, a Puerto Rican gang. Natalie Wood also starred as Maria, the Latina Juliet to Tony's Italian Romeo, despite the fact that both of her parents were Ukrainian.

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Looking back on West Side Story on the 50th anniversary of its release, Rita Moreno—who became the first Hispanic performer to win an Oscar for playing Anita in the film—expressed her discomfort with the "extremely dark" makeup that was used to give all the Sharks a uniform skin tone.

Linda Hunt as Billy Kwan inThe Year of Living Dangerously  (1982)

IMDb, UIP

Despite being a) white and b) a woman, Linda Hunt was named Best Supporting Actress for playing Billy Kwan, a Chinese-Australian photographer who helps Mel Gibson's journalist navigate the tumult of pre-revolutionary Jakarta. Kwan is a dwarf; Hunt stands 4'9". The actress's performance was both widely praised and unencumbered by offensive stereotypes, but whether she should have been cast at all is still a subject of debate more than 30 years later, particularly in light of the fact that high-profile roles for Asian actors were (and remain) few and far between.

William Hurt as Luis Molina in Kiss of the Spider Woman (1985)

IMDb, FilmDallas

Kiss of the Spider Woman, shot in Brazil and set in an unspecified Latin American country, is based on the novel of the same name by Argentine author Manuel Puig. William Hurt—whose ethnic background is entirely European—won Best Actor for his turn as Luis Molina, a feminine and possibly trans prisoner who falls in love with cellmate Valentin Arregui (Raul Julia), a revolutionary that Hurt's character has been ordered to spy on.

Jennifer Connelly as Alicia Nash in A Beautiful Mind (2001)

DreamWorks, CBS

The wife of mathematician John Nash was born Alicia Esther Lopez-Harrison de Lardé in El Salvador. Her Latina heritage is never acknowledged in the biopic, which brought Connelly (who is of Irish, Norwegian, Russian, and Polish descent) the Academy Award for Best Supporting Actress.

If you missed the Last Week Tonight segment on Hollywood whitewashing, watch it here:


Join us on Feb. 28 at 7 p.m. ET as Fusion presents the first-ever All Def Movie Awards, which will celebrate diversity in motion picture entertainment. Hosted by Tony Rock, the awards will include Best Actor, Best Actress, Best Director, and other categories such as Best Bad Muh F**ka, Most Helpful White Person, and Best Black Survivor. Tune in to Fusion’s cable network, or watch the stream on Fusion.net, Facebook, and YouTube.

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Molly Fitzpatrick is senior editor of Fusion's Pop & Culture section. Her interests include movies about movies, TV shows about TV shows, and movies about TV shows, but not so much TV shows about movies.