Ocean's 11 (1960)

The original version of Ocean's 11, from 1960, stars the Rat Pack as a bunch of old army buddies (airborne specifically) who have hit upon a plan to rob 5 casinos of a load of money led by Danny Ocean (Frank Sinatra). The plan itself is fairly simple, go in and rob the places in a blackout at the ringing in of the New Year. The real trick comes in keeping the plan and the identities of the team secret as well as sneak the money out. The main plot complication comes when the casinos (remember that at this time the casinos and hotels on the strip were all run by mobsters) hire an experienced thief, with ties to one of Ocean's team, to get the money back.
The movie isn't a particularly spectacular example of a well-crafted plot or exceptional acting. Most of the actors don't seem to be playing roles in particular, those that actually have well-defined roles rather than just guys walking around in suits. The movie's charm comes from the interactions of the Rat Packers, particularly Dean Martin and Sammy Davis, Jr., with the environment around them. You get an impression of the dangerous glitz of Las Vegas at its taboo heights.
I'd give the movie a C+.