This past Sunday, Leonardo DiCaprio finally won an Academy Award. After five previous nominations, he got an Oscar for his grueling performance in The Revenant. In doing so, he ruined dozens of internet memes - the selfish guy. But those memes existed for a reason: many people believed that DiCaprio deserved an Oscar for one of his earlier roles, and that he's been targeting Oscar-likely roles for a great deal of time now - almost his entire career. Today, we're going to take a look at some of those performances.
#1 The Departed
Prior to The Departed, DiCaprio had teamed up with director Martin Scorsese two times. Both performances were really solid, but the best of the first three was The Departed. A remake of the Hong Kong film Infernal Affairs, the film saw DiCaprio act opposite the likes of Matt Damon, Jack Nicholson, Mark Wahlberg, Vera Farmiga, and Martin Sheen. He starred as Billy Costigan, an undercover police officer. The Departed wound up winning four Oscars, and had one acting nomination, but it was not for DiCaprio. While he wound up getting awards from various other organizations, the illustrious Oscar continued to elude him.