Re-Visiting The Ups And Downs Of Leonardo DiCaprio’s Oscars Journey

leonardo dicaprio oscars 2016

by Katie Rosseinsky |

Leonardo DiCaprio and the Oscars: it’s certainly been a wild ride, and with awards season in full swing, what better time to re-visit the ups and downs of our favourite leading man’s Academy Awards journey?

From his first nomination (at the tender age of 19) through the egregious snubs (where were the awards nods for Titanic and Revolutionary Road?) to the painful near misses to ultimate glory (with a guest appearance from Kate Winslet), we’ve been on Leo’s side every step of the way – though we admit, we may have laughed at some of the Sad Leo memes, and for that, we apologise. Just like the screenplay of any good Oscar-baiting biopic, there might be trials, disappointment and pain along the way, but the uplifting ending is a solid gold crowd pleaser. Your next move, Leo...

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Leonardo DiCaprio Oscars - Grazia

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It's the start of a beautiful relationship. Leo's first Oscar nomination (for Best Supporting Actor, which remains his only nod in this category) came at the tender age of 19, for his role in What's Eating Gilbert Grape. He lost out to Tommy Lee Jones for The Fugitive, but still had a grand old time at the Governor's Ball after party.

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No nominations for Leo this time, but that's no reason not to enjoy the after party scene, right?

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Fast-forward a few years and Leo has netted his second nomination - his first in the Lead Actor category - for The Aviator. Sadly, he loses out to Jamie Foxx, who picks up the award for his role in Ray.

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Would it prove third time lucky for Leo? We all know the answer to this one: the star, nominated for Blood Diamond, lost out to Forest Whitaker for The Last King of Scotland.

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For one hot minute, it seemed that Leo would finally win for his unhinged turned as thoroughly unlikable stockbroker Jordan Belfort in the Wolf Of Wall Street - until Matthew McConaughey rode the waves of the McConaissance all the way to the Academy Awards. And thus, the Internet was saturated with hundreds of 'Sad Leo' memes...

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Together at last: at the 2016 Academy Awards ceremony, Leo finally gets a little gold man to call his own, picking up the Best Actor Oscar for his gruelling turn in The Revenant. The competition (Michael Fassbender for Steve Jobs, Eddie Redmayne for The Danish Girl, Matt Damon for The Martian and Bryan Cranston for Trumbo) never stood a chance – it was always going to be Leo's year.

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What better way to celebrate Leo's Oscar success than with a hug from long-standing BFF and Titanic co-star Kate Winslet? Cue up the Celine Dion - we're feeling tearing just thinking about it.

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After his big win, 2017 saw Leo invited back to the Dolby Theatre, this time on presenting duties. Having presented Emma Stone with her Best Actress statuette for La La Land, the star was spotted walking offstage with a red envelope, leading some Twitter conspiracy theorists to hypothesise that Leo was to blame for the infamous 'envelope-gate' mix up. Of course, he had precisely nothing to do with it…

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