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He tries to court her and is rather unsuccessful until he hypnotizes her and discovers she is a bad girl at heart and wants a blood-thirsty pirate as a lover. She's accepted her fate, though a traveling actor (Kelly) sees this as a waste-as he wants her himself. Judy Garland plays a nice young lady who has been betrothed to the Mayor (Walter Slezak)-a seemingly boring old man. Plus it didn't help that the film was originally meant as a comedy and songs were slapped into the script (sloppily).

Despite having Gene Kelly and Garland and the full MGM glossy treatment, the film didn't connect with folks and it lost money.a lot according to IMDb. So, they re-tooled various parts of the film and released it-to less than stellar reactions from the public. Not only was Judy Garland at her lowest due to her health and her addiction, but the film was considered a mess by the studio when they previewed it. Reviewed by MartinHafer 3 / 10 I can see why this one lost money. Only a miracle can save his neck but Serafin and Manuela manage to arrange one. Serafin, aka Macoco the pirate, is sentenced to death by hanging. Despite his pleas that he only is a circus actor impersonating a pirate, he is found guilty of piracy, partly on fake evidence supplied by a fearful and jealous Don Pedro. Serafin, masquerading as Macoco, is arrested by the Spanish troops. Unfortunately, it also convinces the local authorities and the visiting Spanish Viceroy that he is a wanted pirate. His performance is so well-executed that it convinces everyone, including Manuela, that he truly is Macoco the pirate. He pretends to be the famous pirate Macoco and he plays the part well, assisted by the complicity of his troupe. This revelation persuades Serafin to resort to a trick to woo her. At the circus show, during a hypnosis act, Serafin learns that Manuela is secretly enamored of Macoco. Attracted to each another but, while Serafin wants to woo Manuela, she refuses his advances claiming to be promised in marriage to Don Pedro. She resigns herself to her fate but before the wedding, in nearby Port Sebastian, she meets by chance a troupe of traveling circus actors, led by the handsome Serafin. However, her guardians, her aunt and uncle, aiming to get rich, insist that she marry Don Pedro, the town mayor, an arrogant and bullying much older man. In the Spanish Main, local beauty Manuela Alva, is living on the island of Calvados and dreams of falling in love with the legendary Caribbean pirate known as "Macoco", sometimes called "the black Macoco" due to his fearsome buccaneering and looting.