12. 'The Beach' (2000)
Until it goes off the rails in its final act, Danny Boyle's adaptation of Alex Garland's thriller about a small colony of folks who've settled a remote Southeast Asian island is a moving portrait of generational angst. These Western travelers and backpacking ex-pats are searching for utopia in a highly technologized world, and DiCaprio's charming cockiness comes in handy as his adventurous tourist goes from looking for connections to desperately trying to survive. This highly anticipated film, which was the first project DiCaprio signed on to following his Titanic superstardom, didn't win much love back when it was first released. It's worth another look.