Double Crossbones finds Donald O'Connor as a poor shop apprentice who finds himself nabbed for piracy quite innocently. But before the film's over, O'Connor is the greatest buccaneer of them all, Bloodthirsty Dave.
During the course of his incarceration O'Connor learns that the shop that he and Will Geer worked at was a front for the selling of pirate loot and the guy behind the piracy none other than the governor of the Carolinas, John Emery. In fact Emery has all the pirates of legend that you can name, Henry Morgan, Blackbeard, Captain Kidd, and the famous female pirate Anne Bonney all working for him. And he's getting the best of the deal. They clearly need a better deal and O'Connor puts himself forth as the guy to give it to them. And incidentally win the heart of the beautiful Helena Carter who is Emery's fiancé.
As she usually does, Hope Emerson as Anne Bonney steals the film when she's in it. As Donald O'Connor says, she's best man of the lot of them.
Double Crossbones is a nice satire of pirate movies and O'Connor does fine in the title role. But this seemed to be a film crying for Danny Kaye and I wouldn't be surprised if he was originally offered the lead.
