3. The Scorsese Curse
After years of busting a gut and getting nowhere with the Academy, DiCaprio hit on a role which is usually a guarantee for at least a nomination - The Biopic. Unfortunately for him, there were two issues in 2005: the first was that another Biopic had been made, with a more sympathetic, recently deceased character, and secondly, he was working with Scorsese, who at this point had been grossly overlooked by the Academy a stupid amount of times. Scorsese had worked with DiCaprio a few years earlier on Gangs of New York and was seemingly so impressed that he cast him again in the Howard Hughes Biopic The Aviator. Howard Hughes was not you classic rags to riches story, nor a character who gains much sympathy, but is certainly one that takes research and care to play. The demise of his mental well being was captured perfectly by DiCaprio and should have earned him the Oscar off the bat. Unfortunately for Leo, Jamie Foxx was playing Ray Charles in the film Ray, a musician of immense talent who blind from the age of five and who lived a troubled life from the get go. Now it is not fair to say Foxx didn't deserve his Oscar, because if you have seen him in this role, you will know he does. Maybe this is why there is so much angry chemistry between DiCaprio and Foxx in Django, see boys, everything happens for a reason... But, you could argue that DiCaprio deserved this Oscar just as much as Foxx and is seemingly a victim of bad timing, so bad in fact that it would repeat itself in the cruelest twists of fate just a few years later...