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6 Reasons Why Leonardo DiCaprio Has Never Won An Oscar

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Leonardo DiCaprio is one of the most celebrated and in-demand actors of our generations, yet he’s still yet to bag the biggest prize in acting.

He suffered an all-too predictable Oscar heartbreak back in 2014, missing out on a Best Actor prize to Matthew McConaughey.

Despite rave reviews for his turn in Martin Scorsese’s ‘Wolf of Wall Street’, he was snubbed once again. What does the poor guy have to do to win an Academy award? Why has he not got one already? We investigated…

He’s been unlucky

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First, lets look at his nominations, and who he lost out to.

Leo has been nominated twice before in the Best Actor category for ‘The Aviator’ in 2005 and ‘Blood Diamond’ in 2007.

In those years he lost out to Jamie Foxx in ‘Ray’ and Forest Whitaker in ‘The Last King of Scotland’. Two towering, career-defining performances, much like Tommy Lee Jones’ in ’The Fugitive’ which denied him earlier in his career when he was nominated for ‘What’s Eating Gilbert Grape’.

Ditto 2014. Let’s be clear, Leo is fantastic as Jordan Belfort in ‘The Wolf of Wall Street’. It’s a typically intense performance, but it’s also one that proves he’s got what it takes to do physical comedy too.

However, Matthew McConaughey (who pipped him to the post) is riding the crest of a wave of critical acclaim, in the the biggest year of his acting career. This makes Leo plain unlucky.

He’s TOO consistent

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Since his breakthrough in 1993 with the double-whammy of ‘This Boy’s Life’ and ‘What’s Eating Gilbert Grape’, Leo has consistently made good career moves. His back catalogue is solid, working up from child star, to teen heartthrob, to Hollywood A-lister, taking in a ‘Titanic’ sized mega-hit in along the way.

He’s never really made any major mis-steps along the way (I even rate ’The Beach’) so “where’s the drama in that?” asks The Academy who love a “story” to go with their Oscar-winners. McConaughey – the comeback kid. Daniel Day-Lewis – the method man. And so on.

In fact, Leo doesn’t have a “career-defining” performance yet. Just many, many very good ones.

He doesn’t do “gimmicks”

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Aside from his Oscar-nominated turn as the mentally-challenged Arnie in ‘What’s Eating Gilbert Grape’, Leo has avoided roles that require physical affections or tics, the sort of thing that brings in Oscars.

McConaughey had his “weight-loss”, Colin Firth did the stutter for 'King’s Speech’, Jamie Foxx went “blind” for 'Ray’… the closest Leo’s got is doing a Boston accent for 'The Departed’.

Does Leo need to go full retard (Kirk Lazarus in 'Tropic Thunder’s’ words not ours!) to bag himself an Academy Award? We’d hope not, but it’s got to be worth a shot.

His best work doesn’t get noticed

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It’s hard to define what an “Oscar-worthy” movie is, particularly after ‘Gravity’ defied convention to scoop a ton of awards in 2014, but most years the Oscar-bait tend to be worthy films with weighty subject matters. ’12 Years A Slave’ and ‘The Theory Of Everything’ are good recent examples, but these aren’t the kinds of films Leo tends to make.

If you look back at some of the biggest films of DiCaprio’s career so far - ‘Inception’, ’Shutter Island’, ‘Romeo + Juliet’ - these are popcorn films (even if they were made by top notch directors).

In fact, it’s strange that for most of his most critically acclaimed roles, the aforementioned films, plus ‘The Departed’, ‘Titanic’, ‘Catch Me if You Can’, ‘Revolutionary Road’, he didn’t earn a single nomination.

He’s overshadowed by co-stars

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DiCaprio’s name on your poster is like a stamp of quality assurance. If Leo’s in it, of course it’s going to be good. This allows for actors around him to experiment, to push boundaries, because they’re safe in the knowledge that Leo is there to anchor the film around them.

However, this can sometimes lead to their performances stealing the limelight from Leo. He was mesmerising as slave-trader Calvin Candie in Tarantino’s 'Django Unchained’, but the Academy honoured Christoph Waltz that year instead.

Ditto Daniel Day-Lewis in ‘Gangs of New York’. Mark Wahlberg in ‘The Departed’. Cate Blanchett in ‘The Aviator’, Kate Winslet in ‘Titanic’. Need we go on?

His looks

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From ‘This Boy’s Life’ onwards, Leo was touted as a heartthrob, even squeezing in a turn as the ultimate romantic lead in ‘Romeo + Juliet’ thanks to his boyish, teen idol, good looks. Since the huge success of ’Titanic’, he’s had to work extra hard to choose difficult, less showy roles to escape from that preconception of just being a pretty face. It’s the same problem that Tom Cruise and Johnny Depp face.

He’s never gone full fugly though in his line of work, but why would you want him to, with those matinee idol looks? You’d hope that with his natural talent, that he wouldn’t have to.

Remember, Paul Newman another actor famed for his looks as much as his natural talent was nominated six times before he won in 1986. Chin up Leo, your time will come.

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Image credits: Fox/Warner Bros/PA/REX