40. Con Air
Director: Simon West
Stars: Nicolas Cage, John Cusack, John Malkovich, Monica Potter, Ving Rhames, Mykelti Williamson, Nick Chinlund, Rachel Ticotin, Steve Buscemi
Poor, wrongly imprisoned Nic Cage gets released, then has the gosh-forsaken luck to be on a prisoner transport plane full of insane killers and Dave Chappelle—who then of course take over the plane. You name the creepy movie badass—John Malkovich, Steve Buscemi, Danny Trejo—and they're in it. A classic ensemble murderfest.