Ocean's 11 (1960).

The Scoop:
It's Vegas, baby! The Rat Pack was groovy, and this film presents them at their height.

All the usual suspects are here (Frank Sinatra, Dean Martin, Sammy Davis, Jr., Angie Dickinson, Joey Bishop, Peter Lawford) as well as a few other familiar ones (Cesar Romero, Norman Fell, Henry Silva, Akim Tamiroff), in this tale of Danny Ocean (Sinatra at his coolest) who brings together his old army buddies to pull off a daring heist -- robbing the five major Las Vegas casinos simultaneously at the stroke of midnight on New Year's Eve. Director Lewis Milestone keeps the pace lively and fun, and the camaraderie between the Rat Packers is palpable on screen. Even though it clocks in at more than two hours, it flies by when you feel like you're in the company of old friends.

If you're a fan of old school Vegas or vintage midcentury modernism, this film has everything you need. Sure, Steven Soderbergh's 2001 remake might have had some good action and the presence of Clooney, Pitt, Damon, et al., but it still can't touch the original for great music, plenty of swingin' attitude and vintage Vegas atmosphere.

Best Line:
"I'm so drunk, I don't think I could lie down without holding on!" (This is a punchline to an old Dean Martin routine, which was borrowed by Shirley MacLaine when she ad-libbed her cameo appearance.)

Side Note:
Because all the stars were such good pals, they ad-libbed big chunks of the dialogue, with a lot of the material coming from in jokes and private references.

Companion Viewing:
"Swingers" (1996) and "Ocean's 11" (2001).

Links:
IMDb.
Fan page with sound bites.

Take a Look:
The trailer:


Sammy Davis Jr. sings "Ee-O 11":