Ocean's 11 (1960)

Danny Ocean (Frank Sinatra) calls on some of his World War II buddies -- including Jimmy Foster (Peter Lawford), Sam Harmon (Dean Martin) and Josh Howard (Sammy Davis Jr.) -- to pull off an elaborate New Year's Eve heist at five casinos in Las Vegas. Eleven members of Danny's crew come together to pull off a perfect robbery, but they suffer a series of setbacks when Duke Santos (Cesar Romero), a former gangster, tries to thwart Ocean's plans to disappear with the money.