Abbott and Costello Meet Captain Kidd (1952)

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 Kidd's treasure map of Skull Island. Kidd's 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.