From sinking ships, to golden statues: the career of Leonardo DiCaprio

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The campaign for Leonardo DiCaprio to win his very first Academy Award – which he dutifully collected for his performance in The Revenant – had almost overshadowed the annual event, as the only aspect people could speak about in the hours preceding the start of the ceremony.

There has been a general consensus that the actor has been hard done by, unfortunate to have not yet got his hands on the prestigious award for Best Actor, despite having been nominated on three other occasions, for his performances in The Wolf of Wall Street, Blood Diamond, The Aviator – as well as a nod back in 1994 in the Best Supporting category, for his turn in What’s Eating Gilbert Grape.

Now, however, he – and his vast array of supporters (many of which had travelled to London’s Odeon Leicester Square to celebrate the inevitable victory) can rejoice, for he won the seemingly long overdue accolade for the very first time. Having now done so, we’re chronicling what has been truly an illustrious career, and determining exactly why so many felt this deserved award had been such a long time coming.


Leicester Square’s Odeon’s went all out for Leo to win.

DiCaprio made his cinematic bow as just a teenager, in the all too forgettable Critters 3. Don’t worry, we haven’t seen it either. It wasn’t until two years later, in 1993, when he landed his first truly significant role on the silver screen, acting opposite Robert De Niro in This Boy’s Life. At the age of 19 the Hollywood-born actor was considered something of a teen heartthrob, and his projected career in cinema had the potential to reflect that – a notion he eventually went on to gloriously subvert.

What’s Eating Gilbert Grape epitomised this idea, of a young actor that while prime for romantic leads, was hoping to achieve more, to test himself as a character actor and prove there’s far more to his demeanour than a mere pretty face – something which had taken fellow Oscar winner (back in 2014) Matthew McConaughey a rather longer period to establish.


A young Leo in 1993’s ‘What’s Eating Gilbert Grape’

In spite of his young age, DiCaprio was forging a reputation for himself as one of the industry’s most dependable leading men – taking starring roles in The Quick and the Dead, The Basketball Diaries and Total Eclipse. Then came the two projects which confirmed his worldwide status and acclaim – in the cult favourite Romeo + Juliet by Baz Luhrmann, and the box office phenomenon Titanic (with Marvin’s Room sandwiched in between).

On the surface both films appear to be somewhat generic love stories, but DiCaprio transcended such a notion, adding a sense of subtlety and nuance to the roles at hand, certainly proving himself as being so adept in this field when bringing so much to one of Shakespeare’s most renowned character creations. The sky was now the limit, and it seemed DiCaprio could do no wrong, with a freedom whereby he could head down any path he so desired. Thankfully, for both the actor and for us, he chose that of Martin Scorsese’s.


The iconic shot of DiCaprio & Winslet in James Cameron’s ‘Titanic’.

Having worked with Woody Allen on Celebrity and Danny Boyle on The Beach, DiCaprio was evidently searching for filmmakers and auteurs to inspire him, and challenge him – and his first collaboration with Scorsese – which has since prospered into a glorious working relationship – came in Gangs of New York. We were seeing a maturer side to the actor now, as the faith bestowed on him by some of cinemas true greats was paying dividends, proved again in Catch Me If You Can, where he teamed up with Steven Spielberg.

DiCaprio was taking on a different kind of role now, long were the days of the star-crossed, juvenile lover, and now he was more likely to be found playing the boss of a company, and not the intern, the father, and not the son – and he flourished. The Aviator (one of his finest performances to date – followed) which then led into The Departed. DiCaprio was becoming an integral component in Scorsese’s career, collaborating almost as often as the director once did with De Niro – an actor now too old to play the roles that had been written, graciously, and triumphantly tackled by DiCaprio instead.


Looking more grown up in Scorsese’s ‘The Aviator’.

Blood Diamond was next up, followed by Body of Lies with Ridley Scott. There aren’t many of the world’s leading directors DiCaprio was yet to work under, as he then took on roles in Sam Mendes’ Revolutionary Road, and Chris Nolan’s Inception – with Shutter Island (another of Scorsese’s in between). Then came J. Edgar with Clint Eastwood and Django Unchained with Quentin Tarantino, before a reunion with Luhrmann in The Great Gatsby.

However in a sea of impressive performances in truly accomplished endeavours, there weren’t many guaranteed Oscar winners amongst them. None that you felt he was robbed by not getting his hands on an Academy Award. That changed with The Wolf of Wall Street – in what was a stunning performance in the leading role of Jordan Belfort – but his campaign was to no avail.

But then, at long last, he was rewarded – for playing Hugh Glass in Alejandro Gonzalez Inarritu’s The Revenant, undoubtedly the strongest of the five nominees for the Best Actor accolade.


Bracing the cold in his oscar-winning performance for ‘The Revenant’.

But this didn’t just feel like an Oscar for a sole performance (despite the fact it definitely should be judged on that merit and that merit alone), but instead this felt like an acknowledgement for what has been a glorious career. We’ve grown up with DiCaprio, and have seen him mature and develop as an actor and a person across the past two decades, and so there was something more personal about this Oscar, as an actor so many feel an intimate connection to. Guess that could explain why we all call him Leo.

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About Stefan Pape

Stefan Pape is a film critic and interviewer who spends most of his time in dark rooms, sipping on filter coffee and becoming perilously embroiled in the lives of others. He adores the work of Billy Wilder and Woody Allen, and won’t have a bad word said against Paul Giamatti.

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