Leonardo DiCaprio: The Long and Winding Oscar Road

DiCaprio portraying legendary trapper Hugh Glass in The Revenant

I’m a believer in that everyone has their moment and for Leonardo DiCaprio, that time has finally come. After years of being overlooked by the Academy, DiCaprio finally won an Oscar for his role in the thriller The Revenant. It is surprising to many that it’s taken so long considering the calibre of DiCaprio’s body of work and many feel that he should have won an Oscar much sooner. Let’s take a look at his previous nominations.


First nominated for ‘Best Actor’ way back in 2005 for his role in The Aviator, this is the role that most feel Leo should have won for. Leonardo was electrifying as Howard Hughes, an eccentric billionaire who revolutionised both the film and aviation industries in the 1920’s. Wolf of Wall Street was Leo’s most recent nomination in 2013, playing the role of Jordan Belfort, a Wall Street stockbroker who is convicted of fraud. He was both magnetic and charismatic as the disgraced stockbroker, it’s just unfortunate that the global financial crisis probably left a bad taste in everyone’s mouths regarding the industry.

Leo’s previous Oscar nominations –

DiCaprio in What's Eating Gilbert Grape
DiCaprio in What’s Eating Gilbert Grape


1994 — What’s Eating Gilbert Grape, Best Supporting Actor
2005 — The Aviator, Best Actor
2007 — Blood Diamond, Best Actor
2014 — Wolf Of Wall Street, Best Actor And Best Picture

There are movies in Leo’s filmography where he wasn’t nominated for an Oscar but still provided a stellar performance. In the brilliant Catch Me If You Can, DiCaprio uses his charisma and charm effectively in the role of Frank Abagnale Jr, a very famous conman. And of course, Titanic – the movie that made both DiCaprio and Kate Winslet household names. The movie won Best Picture and Winslet was nominated for the Best Actress Oscar but DiCaprio was snubbed.

But all’s well that end’s well as DiCaprio now finally has that Oscar he has been dreaming of for over a decade.