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Not Just Leonardo DiCaprio: Hollywood's Unluckiest Oscar Contenders

Writer's picture: Tom GoedhartTom Goedhart

As the 88th Academy Awards approaches, all eyes are once again on Leonardo DiCaprio. It’s almost become tradition - year after year, Leo’s fans rally behind him, willing him to finally clutch that elusive golden statue. Back in 2014, his electric performance in The Wolf of Wall Street was deemed Oscar-worthy by many, yet he watched the award go to Matthew McConaughey. Now, with his physically demanding role in The Revenant, the question looms: will this be the year Leo finally breaks the curse?


In anticipation of the ceremony, Yahoo News released a list of Hollywood’s most talented yet unlucky stars and filmmakers who’ve also missed their Oscar moment. Perhaps it’s their way of letting Leo know he’s not alone in his struggles. Let’s take a look at some of the industry’s most notable “always-the-nominees-but-never-the-winners.”


Leonardo DiCaprio

Six nominations. Twenty years. Still no Oscar. Leo’s journey began when he was just 22, earning his first nod for What’s Eating Gilbert Grape. Now, at 41, the world is holding its breath for his sixth chance with The Revenant. Is the sixth time the charm?

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  • Best Supporting Actor: What’s Eating Gilbert Grape (1993)

  • Best Actor: The Aviator (2005)

  • Best Actor: Blood Diamond (2007)

  • Best Picture (Producer): The Wolf of Wall Street (2014)

  • Best Actor: The Wolf of Wall Street (2014)

  • Best Actor: The Revenant (2016)


Robert Downey Jr.

Despite being the highest-paid actor in Hollywood and beloved as Tony Stark, Robert Downey Jr. is still waiting for his Oscar moment.

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  • Best Actor: Chaplin (1993)

  • Best Supporting Actor: Tropic Thunder (2009)9)


Ridley Scott

With a career spanning decades and iconic films under his belt, it’s shocking that this British directing legend has never claimed an Oscar.

RIdley-Scott

  • Best Director: Thelma & Louise (1991)

  • Best Director: Gladiator (2000)

  • Best Director: Black Hawk Down (2001)

  • Best Picture: The Martian (2015)y)


Spike Lee

Though Spike Lee received an honorary Oscar in 2015, the visionary filmmaker continues to seek a competitive win to solidify his legacy.

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  • Best Documentary Feature: 4 Little Girls (1988)

  • Best Original Screenplay: Do the Right Thing (1990)


Peter O’Toole

The late Peter O’Toole was nominated an astounding eight times without ever winning, leaving behind a bittersweet legacy.

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  • Best Actor, Lawrence of Arabia (1962)

  • Best Actor, Becket (1964)

  • Best Actor, The Lion in Winter (1968)

  • Best Actor, Goodbye, Mr. Chips (1969)

  • Best Actor, The Ruling Class (1972)

  • Best Actor, The Stunt Man (1980)

  • Best Actor, My Favorite Year (1982)

  • Best Actor, Venus (2006)


Richard Burton

A seven-time nominee and former husband of Elizabeth Taylor, Burton’s Oscar-less career is a glaring omission in Hollywood history.


  • Best Supporting Actor, My Cousin Rachel (1952)

  • Best Actor, The Robe (1953)

  • Best Actor, Becket (1964)

  • Best Actor, The Spy Who Came in from the Cold (1965)

  • Best Actor, Who’s Afraid of Virginia Woolf? (1966)

  • Best Actor, Anne of the Thousand Days (1969)

  • Best Actor, Equus (1977)


Glenn Close

With six nominations, Glenn Close shares the record for the most Oscar nods for an actress without a win.


  • Best Supporting Actress, The World According to Garp (1982)

  • Best Supporting Actress, The Big Chill (1983)

  • Best Supporting Actress, The Natural (1984)

  • Best Actress, Fatal Attraction (1987)

  • Best Supporting Actress, Dangerous Liaisons (1988)

  • Best Supporting Actress, Albert Nobbs (2011)


Alfred Hitchcock

The master of suspense, Hitchcock’s five nominations for Best Director never translated into an Oscar win.


  • Best Director, Rebecca (1941)

  • Best Director, Lifeboat (1945)

  • Best Director, Spellbound (1946)

  • Best Director, Rear Window (1955)

  • Best Director, Psycho (1961)


Tim Burton

Surprisingly, the imaginative director has only been nominated twice, both for animated films.

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  • Best Animated Feature: Corpse Bride (2006)

  • Best Animated Feature: Frankenweenie (2013)


Johnny Depp

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From pirate to barber, Johnny Depp’s three Best Actor nods remain unfulfilled dreams.

  • Best Actor, Pirates of the Caribbean: The Curse of the Black Pearl (2003)

  • Best Actor, Finding Neverland (2004)

  • Best Actor, Sweeney Todd: The Demon Barber of Fleet Street (2007)


Cary Grant

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The Hollywood legend retired four years before receiving an honorary Oscar, leaving fans to wonder what could’ve been.

  • Best Actor: Penny Serenade (1941)

  • Best Actor: None But the Lonely Heart (1944)


Sigourney Weaver

With a double Golden Globe win in 1988, Sigourney Weaver seemed destined for Oscar glory. Yet, her nominations fell short.

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  • Best Actress, Aliens (1986)

  • Best Actress, Gorillas in the Mist (1988)

  • Best Supporting Actress, Working Girl (1988)


From overlooked legends to modern-day stars, the Oscars don’t always recognize talent when it’s due. As for Leo, perhaps this year will finally break the streak and grant him the recognition he deserves - or he’ll join the ranks of these iconic “Oscar unluckies.”


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