I think the title says it all...why doesn't he? He has been nominated five times and yet no wins. Despite those five nominations I can think of several other films that he should of at least been nominated for.
Nominations are as follows: 1994-What's Eating Gilbert Grape, 2005- The Aviator, 2007-Blood Diamond, and 2014- Wolf of Wall Street.
I would like to add that he deserved at least a nomination for: 2011-J Edgar, 1995- The Basketball Diaries, 2010- Shutter Island.
He has yet to walk home with the Golden Man despite some of the best performances one can give, so what gives? Many have said that even though each performance he gave those years he was nominated someone else was better. I think that is subjective and so are the awards so I have to chuck it up to that but at the same time Leo always brings the A game. I can see a film being released and told Leo is in it and I am sold, despite not knowing what the film was even about. Originally is was because, well he is good looking, but as I grew to appreciate film more I was always in awe of his performance. The fact is this he has a new movie coming out: The Reverant and from the looks of the trailer this will be Leo's year. Let's keep our fingers crossed.