The Big Lebowski
The Coen Brothers have created perhaps the best ever adaptation of a Raymond Chandler novel, even though this isn't actually based on any of his novels (it just feels like one). The Big Lebowski is laugh-out-loud funny from beginning to end; there are so many intricate layers of humor to the film, from a multitude of references to past films to the fact that the whole "plot" is driven by the actions of nihilists. With that last part in mind, don't even try looking for a point to the movie or you might miss it entirely. Just chill out on the couch and enjoy a lazy evening of intrigue, mystery and bowling with The Dude and his eccentric friends.