The curse of Leonardo DiCaprio: 5 times he should’ve won an Oscar

Leonardo DiCaprio is an Oscar nominee once again. On Thursday his performance as fur trapper Hugh Glass in The Revenant earned him his sixth nomination (fifth for acting), nudging him closer to that elusive golden statue.

He has become an Alexander the Great searching for the Fountain of Youth, a Captain Ahab obsessed with Moby Dick. And there have been several times he’s come close. Close enough to touch victory only to have it snatched away. He has deserved to win every single one of those times. And now, he’s as close as ever.

DiCaprio is always the fan favourite at the Oscars, having made his mark as a teen heartthrob before becoming the serious actor that he is now. He is, after all, one of the few mainstream movie stars who can always be counted on to deliver a consistently brilliant performance, regardless of the role. Breaking out in Titanic, the biggest movie of all time must’ve also helped.

Read: The Danish Girl review: Even Redmayne can’t save this shrug of a film

But Jack Dawson seems so long ago now, after we’ve seen him eat raw bison liver, drive a Lambo in a quaalude-induced daze and literally smear his blood on Kerry Washington’s panic-stricken face.

Recently however, DiCaprio seems to have shifted his focus exclusively to winning that long-overdue Academy Award. And with every loss, he becomes more driven, more adventurous with his roles. We’ve listed the five times the Hollywood superstar deserved a win at the Oscars, but for some reason that is beyond all us living souls, did not.

The Basketball Diaries

This was possibly the earliest sign of DiCaprio’s greatness. Even more so than What’s Eating Gilbert Grape. Both DiCaprio and co-star Mark Wahlberg would go on to greater glory in The Departed. But DiCaprio’s performance as a troubled youth coming of age in a gritty, drug fuelled New York is so heart-wrenchingly good, it’s almost painfully great.

Blood Diamond

DiCaprio’s perfect accent (it’s Rhodesian, not Zimbabwean), and his ability to bring out the emotion even behind what most would consider generic action scenes is unmatched. Let’s be honest: Blood Diamond had no reason to be as good as it is. And a lot of that is because of DiCaprio. Even after all these years, we can’t really imagine anybody else as Danny Archer.

The Aviator

The fact that there are so many scenes from The Aviator that are imprinted in our heads is enough to convince us of its greatness. DiCaprio’s partnership with Martin Scorsese would result in many memorable movies, and yes, we have more in this very list. But just that one scene of Howard Hughes losing his mind in the solitude of his messy existence is enough. And The Aviator was full of such scenes. Still, no Oscar.

The Wolf of Wall Street

There was no other performance in 2013 (yes, even Matthew McConaughey’s Oscar winning one) that was as insanely impactful as DiCaprio’s Jordan Belfort. He was playing, in essence, one of the most despicable characters ever. And somehow, in his own unique way, DiCaprio managed to bring out his humanity, while at the same time fully embracing Belfort’s nastiness. Remember that inspirational monologue with the lions and cocaine and freeze frames? It’s enough to make Gordon Gekko look over his shoulder.

Django Unchained

He wasn’t even nominated for this. Decades will go by and Monsieur Calvin Candie will always be remembered, Oscars be damned. Co-star Christoph Waltz’s interchangeable shrug of a performance, however, will no doubt be forgotten, or worse, meld into an all-encompassing mess of Christoph Waltzness. But let’s get back to DiCaprio for a moment, who once again played a man so irredeemably bad and did it with such glee that it becomes impossible to look away. Even when he feeds a slave to dogs. You can’t turn away.

So come February 28th, the whole world will be waiting and watching. This is his best shot at the prize. There’s no 50 kg Matthew McConaughey in his way. It’s his Oscar to lose. And not just because he ate raw meat and almost froze to death. The Revenant is a truly great example of movie-making. And DiCaprio is, as usual, the heart and soul of it all.

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The author tweets @NaaharRohan.