7 Reasons Leonardo DiCaprio Hasn't Won An Oscar Yet

2. His Predilection Towards Big, Flawed Characters Might Have Actually Hindered Him

So far in his career Leonardo DiCaprio has, in no particular order, played these men: Arthur Rimbaud; Howard Hughes; one half of Romeo and Juliet; Jay Gatsby; J. Edgar Hoover; King Louis XIV; Jordan Belfort; and Frank Abagnale Jr. What these men all have in common is not necessarily that they're all incarnations of either famous literary or historical figures, but rather that they're all towering ones. One of the most iconic tragic poets of all time. A film director-cum-Aviation pioneer. One of Shakespeare's most enduring characters. The central figure of The Great American Novel. The founder of the FBI. The King of France. Two notorious corporate criminals. What's more, they're all doomed people; brilliant, yes, but also by turns nasty, selfish and insecure. And while, of course, The Academy loves a biographical turn, it remains that DiCaprio's, good as they can be (and he's especially good as Gatsby and Hughes), might have been a little too bereft of the good old triumph-over-adversity narrative that Oscar loves so much (think Eddie Redmayne winning as Stephen Hawking, or Adrien Brody's win for The Pianist). It might've served DiCaprio better had he taken a few more everyman roles, something possibly more in keeping with McConaughey's work in Dallas Buyers Club. This might've balanced out his performances as big historical figures a bit, lending the actor a perhaps wider range in the process. As it stands, we, and therefore The Academy, are too used to seeing DiCaprio go Big (capital B) - and go home empty handed as a consequence.