Through a series of complicated plot points, store clerk Davey Crandall (Donald O'Connor) pretends to be the dread pirate Bloodthirsty Dave, scourge of the Carolinas.
The Brotherhood of the Coast, a band of famous pirates, welcome Bloodthirsty Dave and begin planning their next criminal move. Will Davey become caught up in their cutthroat plans? Will the authorities ever believe that he's not really a pirate? Will his lady love spurn him for his fictional past?
The outlawed group includes Alan Napier as Captain Kidd, Robert Barrat as Henry Morgan and Hope Emerson as a lusty (and hilarious) Ann Bonney who makes eyes at Davey.
Historical inaccuracies aside, this is a fun film that's not meant to be taken seriously. There are sword fights, people saying "shiver me timbers," and other movie pirate tropes.
To speak with his love interest Lady Sylvia (Helena Carter), this non-outlaw outlaw must disguise himself as a dandy, attend a party and risk being caught. It's a series of comic scenes like those found in Bob Hope comedies, like Casanova's Big Night or Monsieur Beaucaire. Only this is one of the few times in a comedy when a disguise actually works for the plot and the audience in the cinema. O'Connor is absolutely unrecognizable in his white wig and facial hair.
For fans of O'Connor's dancing, we are given one mere morsel of a backstage musical dance number on the pretext that Davey will earn escape money by singing and hoofing onstage at a tavern. It's a delightful little ditty that includes running up a wall - a feature of the famous "Make 'Em Laugh" dance the comic would later perform in Singin' in the Rain (1952).
Double Crossbones (1951) is a great comedy, fun for the entire family. Recommended.