7 Reasons Leonardo DiCaprio Hasn't Won An Oscar Yet

6. He Wasn't Even Nominated For His Best Performance

While never anything less than good in the Best Actor roles he's been nominated for, it remains that not a single one is revolutionary. If you can put your hand on your heart and say that Leonardo DiCaprio is pantheon-great in The Aviator or Blood Diamond or The Wolf Of Wall Street, then fair enough, but I suspect that most people here are equating "very good" with "great", and while of course those terms are subjective and diffuse, it remains that none of that trio would rank in any list of groundbreaking performances since 2000 (whereas Jamie Foxx's win for Ray in the year of The Aviator would, as would Chiwetel Ejiofor's nominated performance for 12 Years a Slave in 2013, a loss that reeks far more of snubbery than any of DiCaprio's). In fact, the closest DiCaprio has ever gotten to being truly great is in The Departed, a phenomenal turn which sees him play an everyman for a change (more on that later). However he did not receive a nomination for The Departed because Warner Bros. didn't want to favour him over co-stars Matt Damon and Jack Nicholson, preferring instead to suggest him for nomination for his work in Blood Diamond. DiCaprio, himself refusing to campaign against his co-stars as a Supporting Actor, was subsequently not bought any slots by the studio in that pool, and thus his best ever performance was not nominated in either category. Politics, eh? If DiCaprio had been nominated and lost for The Departed, talk of oversight or a snub would certainly be more justifiable; he is arguably better in The Departed than the Best Actor winner that year (Forest Whitaker for The Last King Of Scotland), and he would've won for a much more deserving film than either that (The Last King of Scotland) or Blood Diamond.