5. Leonardo DiCaprio - Amsterdam Vallon (Gangs Of New York)
Leonardo DiCaprio has proven himself as one of the best actors of his generation over the last decade or so, although - like the movie that the character is inherent to - his performance as Amsterdam Vallon in Martin Scorsese's
Gangs of New York is confused as hell. That's to say, this part was totally wrong for Leo in every conceivable way: I don't know about you, but I would never have thought him capable of playing an angry Irish-American guy clinging to thoughts of life-long revenge. He tries to convey this to the best of his ability, of course, but it's too boyish and uncomfortable to watch - like an actor purposely trying to go against what people know him as to show 'em whose boss and, like, failing. I blame Scorsese for this one, though: he should have known that Leo was wrong for the part from a brief weigh up. I don't think DiCaprio does cocksure very well (though he attempts it a lot), and that's a trait that was kind of crucial to this particular role. Leo also tries his hand at an Irish accent here and ends up sounding insane. His turbulent relationship with accents pays off occasionally, but here it doesn't work at all. Sorry, buddy.