ByJack Carr, writer at
You are the Princess Shireen of the House Baratheon, and you are my daughter.
Jack Carr

Sometimes it seems like the most frequently asked question of our times. Not "What's the meaning of life?", or "If I look a Kardashian directly in the eye will the Devil take my soul?" - something much bigger. Will Leonardo DiCaprio, global icon and acting legend, finally win an Oscar for The Revenant?

If you didn't catch it yet or just want to relive it, here's the trailer...

Don't get me wrong, I understand the curiosity, the need to see this man get some seriously overdue recognition for his vast contributions to cinema ever since he was a fresh-faced, lovestruck Montague in Romeo + Juliet. For twenty years he's powered through iconic role after iconic role, surpassing the Matt Damon's and the George Clooney's and basically everybody else in Hollywood with his longevity and immense box office appeal.

So of course it sucks that he's not yet got his hands on that gold statuette. I see why that's a big deal - but somewhere along the way, we've lost sight of the bigger picture. Actors don't act for an Oscar. It's a reward, not the ultimate end game. They do it because they love it, because they're good at it (in most cases), because they've got more to give to the world than serving Big Macs.

With that in mind, let's rewind and take a look back at 5 Oscar-worthy Leo performances which never quite got the recognition they deserved - but which proved that awards are no substitute for a legacy created.

1. Romeo + Juliet (1996)

Shakespeare's iconic tragedy has to be one of the most performed, adapted and rebooted works of fiction ever written. From Franco Zeffirelli's 1968 classic to the lifeless 2013 remake, the text simply never goes out of style - but it's Australian director Baz Luhrmann's wild retelling Romeo + Juliet that stands out as my personal favorite.

Leo is the definitive Romeo, all bright-eyed optimism and youthful romanticism, gradually infused with frustration and rage as the film gathers pace. For such a young actor - he was just 21 at the time - his performance couldn't be bettered, and the film made such a cultural impact that schools all over the world include it in their English language curriculum.

TL;DR - Leo's breakout role remains one of his finest.

2. Titanic (1997)

A.k.a. the one that established Leo as the ultimate '90s heartthrob, all floppy blonde hair and icebergs and tragic endings. Titanic is a landmark in cinema, but it also marks the exact moment that DiCaprio became ingrained in pop culture. From this point on, we knew that Leo was here to stay.

3. The Departed (2006)

DiCaprio was thirty when he filmed The Departed, and more than any other of his films it represented the sometimes awkward transition point between youthful A-lister and maturing actor ready to take risks with his body of work.

Martin Scorsese's dark, unflinching vision of corruption within law enforcement and the mob saw Leo share the screen with the likes of Matt Damon and Jack Nicholson, but it's his performance as a police academy undergrad sent to infiltrate an infamous organized crime syndicate that lingers longest in the memory.

4. Inception (2010)

Another dark blockbuster, this time helmed by Christopher Nolan fresh off The Dark Knight. Leo digs deep to mine the emotion of a man separated from his wife and kids and prepared to do literally anything to claw back some semblance of the family he lost. Not the best film in this list, but a performance which will go down as one of his best remembered.

5. The Wolf of Wall Street (2013)

Finally in 2014, the Academy recognized Leo for the fourth time (and the first since 2007's Blood Diamond) for his take on Jordan Belfort, the real-life wolf who tore Wall Street a new one with his greed and deception, and lived like a God - until his crimes caught up with him. Resisting the temptation to go overboard, DiCaprio inhabits the arrogant Belfort so thoroughly that it's astonishing we still (kinda) like him by the end of the movie.

The ones that got away...

I didn't even get a chance to talk about Leo's other iconic roles, from The Aviator to Shutter Island to Django Unchained - films that have gone down as modern classics thanks in no small part to DiCaprio's unparalleled screen presence.

But that's precisely my point: Oscars are about appreciation. Recognition. But there's hardly any fan of cinema who doesn't already recognize that this man is a genius, his contribution to the art of film unmatched.

The Oscar would be great. But Leo's not losing any sleep, and neither should you.


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