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Leonardo DiCaprio - Never won an Oscar

Updated on September 2, 2012

Always nominated but never a winner! Dicaprio is easily one of the most overlooked stars in Hollywood. And no matter how hard he tries, there always seems to be someone on the board of the Academy that plain just didn’t like Titanic.

Now I assume we all know who DiCaprio is so I will spare the backstory on him. But I must say that after seeing his earlier work and his latest, I am a fan. I hope this feature will help to explain why I feel Leo deserves an Oscar and also to show how talented but overlooked he really is.

Let’s begin.

Leonardo DiCaprio and Robert DeNiro in This Boy's Life 1993
Leonardo DiCaprio and Robert DeNiro in This Boy's Life 1993

His first movie was Critters 3. Ok I’m not starting off very well here. But if you think about it, starting in a movie like Critters 3 brings hope to me. A movie franchise that should never have been conceived starred a young Leo DiCaprio, the future overlooked star of Hollywood became hugely successful even after this title. Leo never once thought for a second that he could make a living out of acting. At best, he thought he would at least be able to save up some money for college. How wrong was he? But he started to love it and have passion for it. He is just one of those actors that seems like he was meant to be a star.

When DiCaprio was only 16, he starred alongside Robert DeNiro in the hard hitting, powerful drama “This Boy’s Life”. He played the victim of psychological abuse and was forced to witness domestic violence by his stepfather played by DeNiro. This was an incredible film and had some very tense scenes that will resonate with a large portion of the cinema going public.

DiCaprio was very comfortable in such a gritty role at the tender age of 16, and this should have been an early indication of what Leo could do. DiCaprio had honesty about him and he was believable to the point where you could actually see yourself in his shoes.

After winning his first award, a Chicago Film Critics Association Award for his efforts on “This Boy’s Life”, he moved on to star as the mentally disabled brother of Johnny Depp in “What’s Eating Gilbert Grape”. This role would be challenging to anyone as it is sensitive subject matter but this was another opportunity for DiCaprio to show that he just wasn’t scared of challenges, and chose roles that would be difficult, especially at such a young age when he could be doing safer options.

At 19 years old he was cast in the star packed “The Quick and the Dead”, alongside Russell Crowe, Sharon Stone and Gene Hackman. Although this movie is considered a flop, Hollywood was definitely talking about DiCaprio.

Leo in Basketball Diaries 1995
Leo in Basketball Diaries 1995

His next masterpiece was the enthralling “Basketball Diaries” based on the real life memoirs of the same name written by Jim Carroll in 1978 detailing his addictions and his sexual exploration. Leo showcased another captivating performance as the heroin addict that had everything going for him as a basketball player, but threw it all away when he took his first smoke. This was a sensational piece of cinema, and after viewing this a few times I have to say that it can be uncomfortable to watch at times and it’s so hard to take your eyes off the screen. But it proved Leo was definitely a star in the making at this point and he wasn't backing down to a challenge. Already playing very difficult roles, Leo was about to become an overnight sensation.

Baz Lurhmann’s Romeo + Juliette next. And this was Leo’s breakthrough role to a commercial audience in a film adaptation of the 300 year old Shakespeare play. It was a pretty good success at the box office earning almost $150 million in revenue, and catapulted Leo into the eyes of pre adolescent teenage girls and continued to his next big sensation, Titanic.

James Cameron directed a movie that spent more than it should have, took longer than expected and was in danger of mirroring the fate of the Titanic itself. Not a great deal of people had much faith in it before it’s release. But what came of it was well worth the wait as Titanic was a glorious success earning over $2 billion and breaking every record and remained unbeatable for 12 whole years until James Cameron’s movie again, Avatar beat it off the top spot.

Leo didn’t want to be known as the new pin up, so he changed, and worked even harder. Man in the Iron Mask, Celebrity and The Beach all aged the young DiCaprio and made him distinguished, and determined as he made his own choices without caving in to the pressures of Hollywood to go down the same path as Titanic. This worked and he was headhunted by Martin Scorsese for his future title “Gangs of New York” but not before he was personally chosen by Steven Spielberg to star in the 2002 film “Catch me if you can”. Leo has an undoubtedly passionate appeal as he gives his all to us on the screen. When you watch him it becomes apparent that he researched the role beforehand in great detail, as he recites his lines it feels like he didn’t even know he was being filmed. He’s not done yet in his efforts to outdo himself with each project he welcomes. This level of strong will is undeniably a marker for greatness and he has continued this characteristic throughout his career. A feat that only a few have kept hold of in the corrupt world of film making.

Catch Me If You Can 2002
Catch Me If You Can 2002

Scorsese has chosen Leonardo as his personal favourite aside from the DeNiro days and has cast him in 3 movies in a row including The Aviator and The Departed as well as Gangs of New York and Shutter Island. Marty trusts his new protégé’s instincts and his passion fits the profile of the great Scorsese in the foreseeable future. His performance in The Aviator astounded viewers yet again with the versatility he was able to achieve playing another character that Leo seems at home to play. There just doesn’t seem to be any role or project that scares DiCaprio and it really shows with his choices. When I say choices, I mean Leo has earned the right to choose and pursue a part that he wants to play. He moved on to play the Academy Award and Golden Globe nominated character of Danny Archer in Edward Zwick’s Blood Diamond. The performance that nailed the Africana accent and impressed audiences with his efforts on getting that just right. Leonardo is an artist with his craft and a true visionary of our time. It only makes sense to share the name of another great artist and visionary in the form of Leonardo Da Vinci. As these two men were ahead of their time and remained unrecognised for their efforts for some years but to no avail I have faith that Leonardo DiCaprio will get the recognition he deserves some day. And he won’t quit until he does. He doesn't cry about it but instead works harder and grows into his own better than anyone I have seen and for that I salute the true dedication and passion for something he believes in.

Going on to act his ass off in Revolutionary Road, he is now sought after as a sellable and reliable star. And with his work on Christopher Nolan’s Inception, Clint Eastwood’s J. Edgar, Quentin Tarantino’s Django Unchained and Baz Luhrmann’s The Great Gatsby, only time will be the deciding factor for Leo to win what he has earned after all these years and the magnificent performances he has displayed. This talented young actor doesn't walk around being full of himself or demanding respect or importance. He is just quietly brilliant and his Lifetime Achievement Award night will be a sensational one. But he will not rest until he has something to go out on and the mere fact that he hasn't been on James Lipton's "Inside the Actor's Studio" yet and Tom Hanks has been on twice, shows he is his own biggest critic. As for now Leo, you are definitely on your way to legendary status.


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      4 years ago

      this young actor deserved to win an oscar long ago starting with gilbert grape. I hope i live to see it. He not only does quality projects but is a great role model. Doesn't seem to play the party game for exposure. I hope he doesn't continue to be overlooked....a terrigic actor....


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