7 Reasons Leonardo DiCaprio Hasn't Won An Oscar Yet

4. His Nominated Films Have Not Been Overly Rewarded In Other Categories

While it's becoming increasingly rare that the Best Actor winner comes from the eventual Best Picture winner (this has happened only twice since DiCaprio was first nominated for Best Actor in '04), it remains that the Best Actor winner usually stars in a film that gains momentum and wins in other categories. And while The Aviator won a group of Oscars (mainly for technical awards, though Cate Blanchett did win Best Supporting Actress), neither Blood Diamond nor The Wolf Of Wall Street won any of the five Oscars they were each nominated for. Of the fifteen Best Actor-winning performances since 2000, eleven of them have been in films that won at least one other Oscar on the night, suggesting that DiCaprio was never likely to win for films which in hindsight look like they were never much-loved in Academy circles. Things look much better for DiCaprio this year, however, the actor looking more and more like a lock as The Revenant continues to dominate Oscar talk.