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|Paul Newman||Pvt. Harry Frigg|
|Sylva Koscina||Countess Francesca De Montefiore|
|Andrew Duggan||Gen. Newton Armstrong|
|Tom Bosley||Gen. Roscoe Pennypacker|
|John Williams||Gen. Francis Mayhew|
|Charles Gray||Gen. Adrian Cox-Roberts|
|Vito Scotti||Col. Enrico Ferrucci|
|Jacques Roux||Gen. Andre Rochambeau|
|Werner Peters||Maj. von Steignitz|
|James Gregory||Gen. Homer Prentiss|
"It's not who you con. It's how you do it."
Several brigadier generals (American, British, and French) are unexpectedly taken prisoner by the Italians while in the sauna - which is a public relations disaster. The generals are held in an Italian villa run by benevolent Italian Colonel Ferrucci. Being all of the same rank, none is in command and they are forced to plan escapes by committee, with predictably ineffective results.Headquarters devises a plot to free them by sending in Harry Frigg (Paul Newman). Frigg is a private in the U.S. Army who is forever escaping from military stockades. As incentive, he is promised a cushy job after the war. Frigg is promoted to major general so that he will outrank the prisoners. Frigg allows himself to be captured, and is imprisoned in the same jail as the brigadiers. While they are initially skeptical of his rank, he has been given a few personal secrets about them.Frigg discovers a secret passage from his bedroom to the gatehouse outside the villa's fence, which he intends to use to escape with the other generals. Frigg's plan to free all the generals is put on hold when he becomes romantically involved with Countess Francesca De Montefiore (Sylva Koscina), the owner of the castle where they are imprisoned. Eventually the escape plans are reactivated however on the eve of the group's intended escape Colonel Ferrucci announces he is to be promoted to general at midnight the following night, due to the low escape rate in the complex. The group put their escape plans off by a day to ensure the Colonel gets promoted to general at least once, despite knowing the rank will be stripped once they do escape. During the celebration a Nazi Major arrives and after midnight announces that Italy has surrendered to Germany. The Germans take the generals to a high-security prison camp for officers. Escape seems hopeless; however, Frigg eventually frees them all, and ends the war as a second lieutenant in charge of a radio station, using the countess's castle as its base.