How many Oscars should Leonardo DiCaprio have actually won by now?

Let's put it this way: probably more than one.
 By 
Adam Rosenberg
 on 
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Original image has been replaced. Credit: Mashable

Leonardo DiCaprio is going to win his first Academy Award on Sunday night. You might as well get used to that, because it's going to happen. It's not like he ate raw liver and slept inside a horse carcass for fun, right?

The Revenant is like a big middle finger to the Academy. When you're willing to debase yourself to this extent -- and act so hard while you're doing it -- you pretty much can't lose. Expect Leo's acceptance speech to go something like this: "I have literally crawled through the muck on hands and knees for you people. F*ck off."


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If all goes according to plan, this will mark Leo's first Oscar win -- after six nominations in all. But it's hardly the first time he's deserved one.

Let's consider all the times the Academy had the ability to halt the inevitability of The Revenant happening... but didn't.

What's Eating Gilbert Grape? (1992)

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Original image has been replaced. Credit: Mashable

What is it? Gilbert Grape (Johnny Depp) is a 24-year-old grocery clerk who cares for his morbidly obese mother (Darlene Cates) and developmentally stunted younger brother, Arnie (Leo!).

Why he didn't win? Blame Tommy Lee Jones. The veteran actor won his Bald Man Statue for The Fugitive in the same year Leo's Grape performance was up for Best Supporting Actor.

Why it's better than The Revenant:

The Quick and the Dead (1995)

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Original image has been replaced. Credit: Mashable

What is it? A Sam Raimi-directed Western starring Sharon Stone as "The Lady." She rides into town to compete in a gunfighting showdown, and a young Leo -- as "The Kid" -- is one of her opponents.

Why didn't he win? The Quick and the Dead isn't an Oscar-worthy movie, but it's absurdly entertaining to watch Stone and Leo chew up the scenery with co-stars Gene Hackman, Gary Sinise, Lance Henriksen and Russell Crowe.

Why it's better than The Revenant:

The Basketball Diaries (1994)

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Original image has been replaced. Credit: Mashable

What is it? DiCaprio starred in an adaptation of author Jim Carroll's autobiographical account of his high school years, when heroin addiction disrupted his seemingly bright future as a basketball star and a writer.

Why he didn't win? The 20-year-old Leo didn't stand a chance. He acted his ass off, but The Basketball Diaries just isn't a very good movie.

Why it's better than The Revenant:

Romeo + Juliet (1996)

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Original image has been replaced. Credit: Mashable

What is it? A modern spin on William Shakespeare's play, starring Leo and Claire Danes in the title roles. The unique take mixes a present-day setting with the Bard's original writing.

Why didn't he win? Leo and Danes were good enough to pick up a "Best Kiss" win at the MTV Movie Awards, but their chemistry and their grasp of Shakespearean theater wasn't enough to impress the Academy.

Why it's better than The Revenant:

Catch Me If You Can (2002)

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Original image has been replaced. Credit: Mashable

What is it? A Steven Spielberg-directed bio-pic about Frank Abagnale (Leo!), a notorious conman, and the FBI agent (Tom Hanks) that pursued him.

Why didn't he win? Beats us. He wasn't even nominated. DiCaprio being passed over completely for Catch Me If You Can is one of the more egregious oversights in recent Academy history.

Why it's better than The Revenant:

The Aviator (2004)

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Original image has been replaced. Credit: Mashable

What is it? Leo stars in a Martin Scorsese-directed biopic charting the life and work of businessman, aviator, engineer and filmmaker Howard Hughes.

Why didn't he win? Although it scored the most nominations and wins at the 77th Academy Awards, Leo's Best Actor hopes were ultimately crushed by Jamie Foxx, who won for Ray.

Why it's better than The Revenant:

The Departed (2006)

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What is it? A tale of two cops, by Martin Scorsese. On one side is Colin Sullivan (Matt Damon), a South Boston native who is groomed by local crime boss Frank Costello (Jack Nicholson) as a mole inside the Massachusetts State Police. On the other side is Billy Costigan (Leo!), a police cadet from a criminal family who goes undercover in Costello's organization.

Why didn't he win? Scorsese finally had his moment in 2006 when he won his first Best Director award, after eight nominations. Leo wasn't even nominated for this great performance, but that's probably because he had another role up for Best Actor that year.

Why it's better than The Revenant:

Blood Diamond (2006)

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Original image has been replaced. Credit: Mashable

What is it? Two unlikely partners -- South African mercenary Danny Archer (Leo!) and Sierra Leone fisherman Solomon Vandy (Djimon Hounsou) -- work together to recover a rare gem while a civil war rages all around them.

Why didn't he win? He wasn't good enough. Sorry, Leo. Forest Whitaker won that year for his starring role in The Last King of Scotland, and he damn sure deserved it.

Why it's better than The Revenant:

Django Unchained (2012)

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Original image has been replaced. Credit: Mashable

What is it? Quentin Tarantino directed this story of a freed slave (Jamie Foxx) and a German bounty hunter (Christoph Waltz) who set out to rescue the former slave's wife (Kerry Washington) from a ruthless plantation owner (Leo!).

Why didn't he win? Waltz was an Academy darling after his Best Supporting Actor win for Inglourious Basterds at the 82nd Academy Awards. He was recognized again in the same category for Django, and ended up winning -- which left Leo without a nomination. (It's rare to see two nominations for the same movie in one category.)

Why it's better than The Revenant:

The Wolf of Wall Street (2013)

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Original image has been replaced. Credit: Mashable

What is it? Martin Scorsese directs this darkly funny bio-pic about Wall Street stockbroker Jordan Belfort (Leo!), who masterminded corrupt and fraudulent activities at his own Stratton Oakmont brokerage firm during the early 1990s.

Why didn't he win? Wolf supporting player Matthew McConaughey won Best Actor that year for his performance in Dallas Buyers Club. Leo was nominated, but he couldn't bring home the gold in his fifth collaboration with Scorsese -- despite the awesome physicality of his big Quaalude scene.

Why it's better than The Revenant:




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Topics Oscars

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Adam Rosenberg

Adam Rosenberg is a Senior Games Reporter for Mashable, where he plays all the games. Every single one. From AAA blockbusters to indie darlings to mobile favorites and browser-based oddities, he consumes as much as he can, whenever he can.Adam brings more than a decade of experience working in the space to the Mashable Games team. He previously headed up all games coverage at Digital Trends, and prior to that was a long-time, full-time freelancer, writing for a diverse lineup of outlets that includes Rolling Stone, MTV, G4, Joystiq, IGN, Official Xbox Magazine, EGM, 1UP, UGO and others.Born and raised in the beautiful suburbs of New York, Adam has spent his life in and around the city. He's a New York University graduate with a double major in Journalism and Cinema Studios. He's also a certified audio engineer. Currently, Adam resides in Crown Heights with his dog and his partner's two cats. He's a lover of fine food, adorable animals, video games, all things geeky and shiny gadgets.

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