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It's behind you, Leo! (Photo: Jason Merritt/Getty Images)

Leonardo DiCaprio is heavily tipped to win the Oscar for Best Actor at Sunday’s Academy Awards, partly due to his role as legendary frontiersman Hugh Glass in The Revenant, but also partly because the six-time Oscar nominee (five for acting) has never actually won, and many feel his time has come.

But what about all those near misses? Here in listicle form are all the times Leo pulled out all the stops but ended up with nothing.

1. What’s Eating Gilbert Grape? (1993)

Leonardo DiCaprio in What's Eating Gilbert Grape?
(Photo: Giphy.)

Uh-oh. Leo was just 18 when he was nominated in 1993 for his portrayal of Arnie, Gilbert Grape (Johnny Depp)’s brother with a developmental disability. In this scene Arnie discovers the body of his beloved mother, going from glee, to thinking she might be playing hide and seek, to despair in the course of a minute.

The Oscar for Best Supporting Actor that year went to Gene Hackman for Unforgiven.

2. Titanic (1997)

Leonardo DiCaprio in Titanic
(Photo: Tumblr.)

This berg-busting epic bulldozed the 1998 Oscars, getting nominated for a record-breaking 14 awards and winning 11 of them, including Best Picture and Best Director. Kate Winslet was nominated for her performance as Rose, as was everyone who worked on the movie it seemed, from the cast to the people who recorded the sound and designed the dresses. Everyone, that is, except Leonardo. His performance as heroic scallywag Jack Dawson went unrewarded.

3. Catch Me If You Can (2002)

Leonardo DiCaprio in Catch Me If You Can
(Photo: Tumblr.)

Come on, Leo: keep it together.

At the ceremony in 2003 Leonardo wasn’t nominated for his role as Frank Abagnale Jr. in Steven Spielberg’s breezy romp about a conman trying to give FBI agent Carl Hanratty (Tom Hanks) the slip, or for Gangs of New York, his other eligible film that year.

The Academy instead awarded Best Actor to Adrien Brody for The Pianist.

4. The Aviator (2004)

Leonardo DiCaprio in The Aviator
(Photo: Tumblr)

Leonardo scored his second Oscar nomination with his second collaboration with Martin Scorsese, in which he played famous tycoon Howard Hughes as he struggled with obsessive-compulsive disorder. He researched the role by living with someone with OCD and observing his mannerisms for a few days. The prep led to an extraordinary performance.

Did it get him an Oscar though? Nope. He was pipped to the post by Jamie Foxx for Ray.

5. Blood Diamond (2006)

Leonardo’s third nomination came hot on the heels of his second, after he played a ruthless smuggler and ex-mercenary in this American-German thriller.

This time his research involved spending a month with former soldiers of fortune practicing military exercises and hunting in the South African bush, but still it wasn’t enough: The Academy decided to honor Forest Whitaker for The Last King of Scotland instead.

6. The Departed (2006)

Meanwhile his masterly performance as an NYPD undercover cop in another movie out that year, The Departed, didn’t even get a look in…

(Photo: Giphy)

7. Shutter Island (2010)

(Photo: Tumblr)

So close…

8. J. Edgar (2011)

Now we’re talking! Biopics are usually a shoo-in for an Oscar, with Jamie Foxx, Sean Penn and Nicole Kidman, all receiving one for their portrayals of Ray Charles, Harvey Milk, and Virginia Woolf, respectively. Leo went through hours upon hours of hair and makeup in order to turn himself into portly FBI director J. Edgar Hoover, but still—nada.

9. Django Unchained (2012)

Leonardo really upped the ante for this role, giving what could be his most terrifying performance as plantation owner Calvin J. Candie.

He even went so far as smashing a glass while slamming his hand against a table. “My hand started really pouring blood all over the table,” he told The Hollywood Reporter at the time. “Maybe they thought it was done with special effects.”

Blood? Check. Sweat? Check. Oscar? Nope.

10. Wolf of Wall Street (2014)

(Photo: Tumblr)

His performance as repulsive financier Jordan Belfort is hypnotic, hilarious, disturbing—sometimes all at once. The movie’s most memorable sequence is probably the infamous “Quaaludes” scene, where Leo’s character accidentally overdoses on some powerful sedatives that leave him half paralyzed… but still no closer to a statuette.

11. The Revenant (2015)

Could this be the one to do it?

It’s certainly apt that Leo’s FIFTH Oscar nomination for acting in 22 years is for this almighty endurance drama. Reports that he was “raped” by a bear on the set of The Revenant turned out to be greatly exaggerated, but he did jump in a freezing cold river, sleep in an animal carcass, and eat raw bison liver.

Surely 2016 might be his lucky year? Watch this space…

(Photo: Tumblr)

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By Kat Sommers
Kat is a freelance writer for Anglophenia.