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6 Reasons Why Leonardo DiCaprio Has Never Won An Oscar

Leonardo DiCaprio is one of the most celebrated and in-demand actors of our generation, 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 Unluckyleo1First, let’s 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) was riding the crest of a wave of critical acclaim, in the biggest year of his acting career. This makes Leo plain unlucky.

He’s TOO Consistent

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 missteps along the way, 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”leo2Aside 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.

His Best Work Doesn’t Get Noticed

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-Starsleo3DiCaprio’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 mesmerizing 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 Looksleo4From 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, 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. So, chin up, Leo, your time will come.

About shakespeareanwalter

Walt Shakes(@Walt_Shakes) is an award-winning Nigerian writer, poet and veteran blogger. He is a lover of the written word. the faint whiff of nature, the flashing vista of movies, the warmth of companionship and the happy sound of laughter.

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  1. It’s really baffling how fine actors like Leo, Will Smith and Brad Pitt haven’t bagged Oscars sha. Wait, and Tom Cruise sef

  2. I’ve always felt bad for Leo that he always gets nominated,but never wins. He’s such an amazng actor who keeps getting better with each movie,yet, no Oscar. Pele,Leo; if it could finally happen for Julianne Moore,it will happen for u,inugo? Just keep giving us those intense performances.

    • I agree, it finally happened for Julianne Moore and who could believe she just recently won after all the great performances she has been giving us.
      It simple really, if he wants to win that coveted Oscar, he should lose weight or act mental.

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