The Rat Pack – Frank Sinatra, Dean Martin, Sammy Davis, Jr., Peter Lawford and Joey Bishop – star with Angie Dickinson in the original Ocean’s 11.

Eleven pals prepare to carry out a (theoretically) foolproof plan to rob five Las Vegas casinos at midnight on New Year’s Eve. The plan depends on split-second timing, and everything goes like clockwork … at first. But even in this almost perfect scheme, things begin to go wrong.
More About Frank Sinatra (courtesy of Biography.com):

By the mid-1960s, Sinatra was back on top again. He received a Grammy Lifetime Achievement Award and headlined the 1965 Newport Jazz Festival with Count Basie’s Orchestra. This period also marked his Las Vegas debut, where he continued on for years as a main attraction at Caesars Palace. As a founding member of the Rat Pack, alongside Sammy Davis Jr., Dean Martin, Peter Lawford and Joey Bishop, Sinatra came to epitomize the hard-drinking, womanizing, gambling swinger—an image constantly reinforced by the popular press and Sinatra’s own albums. With his modern edge and timeless class, even radical youth of the day had to pay Sinatra his due. As Jim Morrison of the Doors once said, “No one can touch him.”

The Rat Pack made several films during their heyday: the famed “Ocean’s Eleven” (1960), “Sergeants Three” (1962), “Four for Texas” (1963) and “Robin and the Seven Hoods” (1964).