Before Steven Soderbergh made it a franchise, Oscar winner Lewis Milestone (All Quiet on the Western Front) helmed the original hangout heist film. Danny Ocean (Sinatra) heads an 11-man team with plans to rob five Vegas casinos simultaneously. His crew includes the entire Rat Pack (Dean Martin, Sammy Davis Jr., Peter Lawford, and Joey Bishop), who filmed by day and performed by night in those same casinos. Their chemistry is palpable, with much of their interplay ad-libbed. A glitzy, good-natured time capsule, the film features a wide-ranging cast that also includes Angie Dickinson, Red Skelton, and honorary Rat Packer Shirley MacLaine in a cameo shot on a break from The Apartment (she received a car as payment for her services).