When Leonardo Dicaprio failed to win an Academy Award for the fourth time the internet nearly broke down. Who hasn’t been rooting for Jack Dawson to win his much deserved Academy Award for 17 years now? ‘Poor Leo’ began trending on Twitter, while there are already Memes galore screenshotting the actor’s reaction to his The Wolf of Wall Street co-star Matthew McConaughey’s award success. While McConaughey walked up on stage to give thank the Academy, God and himself, we couldn’t help but wonder why Leo has lost out yet again on winning the prestigious award.

leonardo dicaprio oscar lossOnce again Leonardo DiCaprio has missed out on winning an Academy Award

Leo was nominated for his first Academy Award way back in 1994 for his role as Johnny Depp’s mentally handicapped brother in What’s Eating Gilbert Grape. DiCaprio had only been in the biz for five years at this point, but from his flawless and moving performance in the movie it seemed like he was already an old hand as he showed a skill which exceeded his young years. The Academy rightly recognised Leo but he lost out to Tommy Lee Jones who won the award for his role in The Fugitive.

Leonardo didn’t receive his next nomination until The Aviator in 2005. DiCaprio played business magnate and aviator Howard Robard Hughes, who was once one of the wealthiest men in the world. He lost out on the Oscar to Jamie Foxx, who gave a groundbreaking performance as Ray Charles in the biographical movie, Ray. Foxx’s performance was spectacular, not only did he get Charles‘ mannerisms spot on, he also sang and played the piano in the movie.

In 2007 DiCaprio was nominated again, this time for his work on Blood Diamond. He should have won an Oscar sheerly for his superb South African accent, but lost out to Forest Whitaker who played Idi Amin in a very challenging role in The Last King of Scotland.

There was 7 years between DiCaprio’s last nomination and his most recent Oscar nomination. In the time that has passed he has taken on some weighty roles, including Frank Wheeler in Revolutionary Road, J.Edgar Hoover in J.Edgar, Calvin Candie in Django Unchained and Jay Gatsby in Gatsby, but has won awards for none of these, despite how well received they have been. 

Leonardo DiCaprioLeonardo DiCaprio With His Mother Irmerlin at the Oscars 2014

Looking at Leo’s award losses he seems to have an uncanny knack for filming an Oscar worthy performance just at the same time as another actor takes on their career defining role, or simply puts in a performance that is considered more worthy of recognition than DiCaprio's - McConaughey's portrayal of AIDS patient Ron Woodruff being a prime example. It seems a case of poor timing for Leo, who has been nominated for 31 awards yet only won 3 throughout his long career.  It seems truly unbelievable that he is regularly passed over.  We may have cut our losses for Leo back in 1994 as he was so young and there was still plenty of time, but as time has gone on there is a big question mark over why Leonardo DiCaprio still hasn't won an Oscar. 

It may not seem like it to him, having been in the business for so long now, but Leo, you are still young and there will be Oscars aplenty in the future.  For now, just enjoy being a world famous, multimillionaire actor with a string of supermodel girlfriends.

Let's remind ourselves of Leonardo DiCaprio's performance in 'The Wolf of Wall Street':