Ocean's 11 (1960)

Danny Ocean (Frank Sinatra) gathers a group of his WWII soldier buddies to rob five of the major casinos in Las Vegas during New Year's Eve. Directed by Lewis Milestone (ALL QUIET ON THE WESTERN FRONT) whose career dates back to silent cinema, this heist film hasn't worn well and in a rare case of a remake being superior to the original, Steven Soderbergh improved on it in 2001. Perhaps the definitive "rat pack" movie, one's enjoyment of it may depend on your nostalgia for the oh-so-cool and hip antics of Sinatra, Dean Martin, Sammy Davis Jr., Peter Lawford and Joey Bishop. As a heist movie, it takes a full hour of tedious exposition (like Sinatra's on and off marriage with Angie Dickinson, Sammy singing etc.) before it gets down to the actual robbery and by that time, you barely care anymore. As a time capsule piece of fifties Las Vegas, it has some archival interest but it doesn't rank highly in the annals of great heist movies. The massive supporting cast includes Shirley MacLaine, Richard Conte, Red Skelton, Cesar Romero, Akim Tamiroff, George Raft, Patrice Wymore, Henry Silva, Jean Willes, Ilka Chase and Joan Staley.