Can you even think of Las Vegas without that song coming into your head? Considered by some to be Elvis' best movie, it hasn't had quite the staying power of the song, which remains ubiquitous, but it remains a classic of its genre.
Remakes are very rarely necessary, but Steven Soderbergh's take on the story of Danny Ocean and his gang, the roles filled out by a star-studded cast, remains a delightful caper. The two films that followed are less to write home about, but the first Ocean's is still fun to watch.
Not even two bad sequels can quite erase all the goodwill engendered by the first film in the Hangover trilogy. A raunchy ride through a series of adventures and accidents, this very funny movie is the standard by which all "bro movies" should be measured.
A dark comedy to be sure, but Terry Gilliam's adaptation of Hunter S. Thompson's book of the same name is nevertheless as funny as it is trippy - and that's saying something.
Albert Brooks' films tend to be something of an acquired taste, which is odd to me since their humor is so sharp and engaging. One of his funniest movies is 1985's Lost in America, in which he and Julie Haggerty play a couple who decide to give up on the rat race and live off the grid - a plan which goes horribly awry when they stop in Vegas and lose just about everything in a casino.