Leonardo DiCaprio: Ranking Every Performance From Worst To Best

2. Billy Costigan - The Departed

Leo's turn as broken, undercover cop Billy Costigan marks what is without a doubt one of the actor's greatest performances (and was probably his all-time best until our number one pick took its place). In his third collaboration with Martin Scorsese (seriously guys, just get married already) and an adaptation of Hong Kong thriller Infernal Affairs, DiCaprio offers up a wonderfully nuanced portrait of a conflicted yet sympathetic character who finds himself in a terrifying situation, imbuing it with the right levels of paranoia and hysteria. Leo successfully steals the movie out from the likes of Jack Nicholson, Alec Baldwin, Matt Damon and all those other actors whose names we frankly aren't even going to mention, because this is all about Leo, dammit! Leo didn't even get an Oscar nomination for his turn as Billy Costigan, which is - quite frankly - a sin on the part of the Academy. Do you want money, Academy? Is that what's required so that you'll actually acknowledge this guy and all his good work? You're making it so hard for everyone, you know. Is this... is this some kind of sick joke to you?