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Two hapless waiters in a tavern on the Spanish Main play cupids between aristocratic Lady Jane and tavern co-worker Bruce Martindale, but the two bumpkins mix-up a love letter with Captain Kidds treasure map of Skull Island. Kidds treasure is claimed by Captain Anne Bonney, and she accompanies the notorious pirate to the island with the boys and Bruce, who have been shanghaied and the captured Lady Jane.
In the late seventeenth century, Captain Kidd and his pirates dock on the island of Tortuga for some recreation. Meanwhile, Rocky Stonebridge and Oliver "Puddin Head" Johnson, who are working as tavern waiters for their passage back to America, are asked to deliver a love letter from Lady Jane to the taverns singer, Bruce Martingale. Before they can deliver the letter, Puddin is sent to wait on Kidd, who is dining with his rival, the beautiful Capt. Bonney. Accusing Kidd of pillaging in her "territory," Bonney demands that stolen jewels be turned over to her. When Kidd claims they are buried on Skull Island and shows her a treasure map, she decides to accompany him there on his ship, with her own ship following, in case of trouble. Their discussion is interrupted by Puddins bungling entrance with the food, and during the resulting disorder, the treasure map and Janes love letter are inadvertently switched. When Rocky and Puddin discover the mix-up, Rocky realizes the importance of the map. They try to trick Kidd into taking them to the island by disguising Puddin as an important naval officer, but the disguise is discovered. To save Puddin from Kidds wrath, Rocky tells him they have hidden the map, and then negotiates for Kidd to take them to the island and share the wealth. As Rocky and Puddin return to the ship with Kidds first mate Morgan and the other pirates, Puddin tosses what he thinks is the love letter to Bruce, who, wondering why his friends gave him a map, follows them to ask, and is shanghaied. On the ship, Kidd searches Puddin and Rocky for the map, planning to feed them to the sharks afterward, but finding only the love letter, he puts them in irons. Enticed by the love letter she thinks Puddin wrote, Bonney frees them, in return for the map, but discovers later that they gave her the love letter. When an English merchant ship, in which Jane is a passenger, approaches, a sea battle commences, and Jane is captured. In exchange for Janes life, Oliver gives Kidd the map. Later Puddin stumbles into Bonneys room and discovers that her ardor for him is getting hotter. However, Rocky pulls Puddin away to search the captains room for the map, which Puddin memorizes, then eats, just before Kidd catches him. At the sight of Skull Island, they all disembark and row out to search. Ordered to lead them to the treasure, Puddin finds a spot and begins digging, while Jane and Bruce find a spot to continue their courting. After several hours, Puddin uncovers a chest filled with jewels, but Kidd, who feels obligated to remain true to his reputation, announces his plans to double-cross all of them. Knowing she is to be killed later that evening, Bonney saves Puddin and Rocky from a live burial and proposes a means of escape. That evening, according to Bonneys plan, Jane and Bruce distract the pirates, while Bonney signals to her ship. Puddin knocks out Kidd and steals his clothes, then posing as Kidd, rescues Jane from the pirates. Bonneys men then fire their cannon at Kidds men, while Bonney and the rest of her new cohorts prepare to carry the treasure by boat to the ship. In his disguise, Puddin is mistaken by Bonneys men for Kidd and fired upon, but he survives. Kidd, Morgan, Rocky and Puddin lead each other on a merry chase, but eventually Kidd is captured and hung by his feet on the ships yardarm and Morgan volunteers to become a loyal second mate. After Puddin and Bonney share a noisy and passionate kiss, Puddin takes over as skipper and they all sail away.
Bud Abbott
Rocky Stonebridge
Lou Costello
Captain 'Puddin' head' Feathergill
Charles Laughton
Capt. William Kidd
Hillary Brooke
Capt. Bonney
Bill Shirley
Bruce Martingale
Leif Erickson
Morgan
Fran Warren
Lady Jane
Phil Bloom
Pirate
Willie Bloom
Pirate
Albert Cavens
Tavern Patron
George DeNormand
Pirate
Lester Dorr
Waiter at Pub
Joe Garcio
Pirate
Frank Hagney
Pirate
Kenner G. Kemp
Pirate
Joe Kirk
Flirtatious Pirate
Rex Lease
Waiter at Pub with Black Eye
George Magrill
Pirate
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