A guide to pirate movies

SHAVER ME TIMBERS The fourth Pirates' characters don't believe in facial grooming.

Disney Enterprises

This week, Johnny Depp reprises his role as Jack Sparrow in Pirates of the Caribbean: On Stranger Tides (which opens Friday 20), the fourth film in the series. The sense of déjà vu we’re feeling extends past the original trilogy to the films that inspired it. While Depp and Co. beat their dead (sea)horse, we offer a guide to the best and worst pirate flicks.

Captain Blood (1935)
The hook Convicted of treason for saving the life of an enemy soldier, an idealistic doctor gets sold into slavery, escapes, steals a Spanish vessel and reinvents himself as a devil-may-care buccaneer.
Swashbuckling star Errol Flynn, minus his signature pencil-thin ’stache, in the role that cannon-fired him onto the A-list
Aristocratic damsel with a feisty streak Perennial Flynn love interest Olivia de Havilland, in her first of eight pairings with the dapper leading man. She’s charming enough to make us forget her character is basically a wealthy slave owner.
Respectable actor slumming it as a dastardly villain Sherlock Holmes himself, Basil Rathbone
Saltiest put-down “You’ve the looks and manners of a hangman.”
Worth its weight in treasure? Yes. Every actor who’s wielded a rapier since—including Depp and Orlando Bloom’s Pirates protagonists—owes a cut of his bounty to Flynn.

The Black Swan (1942)
The hook There are no crazy ballerinas here, just a reformed outlaw charged with ridding the Caribbean of his plundering peers.
Swashbuckling star Tyrone Power. Forget that preening pretty boy Flynn. Power is the man’s man of this genre.
Aristocratic damsel with a feisty streak Maureen O’Hara. She’s plenty feisty, but not enough to avoid succumbing to Stockholm syndrome—and with a hard-drinking cad who literally knocks her out in their first meeting, no less.
Respectable actor slumming it as a dastardly villain George Sanders, unrecognizable beneath an awesomely bushy, fire-red beard
Saltiest put-down “Your eyes. I’ve looked into pistol barrels that are warmer.”
Worth its weight in treasure? Yes. O’Hara and the Technicolor cinematography are gorgeous. And did we mention Sanders’s beard?

Pirates (1986)
The hook Loony Captain Red, forced into slavery aboard a Spanish galleon, stages a mutiny and tries to get his grubby mitts on a golden Aztec throne.
Swashbuckling star Walter Mathau, sporting a pretty convincing wooden appendage and an entirely unconvincing Cockney accent
Aristocratic damsel with a feisty streak Newcomer Charlotte Lewis—although as in the first Pirates of the Caribbean, the hero is too grungy to merit a love interest, so the lady gets linked to a sidekick.
Respectable actor slumming it as a dastardly villain BBC veteran Damien Thomas
Saltiest put-down “You son of a double-eyed whore from the reeking gutters of Rotterdam!”
Worth its weight in treasure? Yes and no. The film, featuring the “comedic” devouring of live rats and other barfworthy gags, is considered the worst of Roman Polanski’s career. It’s spectacularly miscalculated, but there’s something perversely endearing about its tasteless spoofing of high-seas adventures.

Cutthroat Island (1995)
The hook A cocksure pirate competes with her murderous uncle for three connecting scraps of a treasure map.
Swashbuckling star Geena Davis. That’s right, this rakish scallywag is a woman. It’s the only original element in Renny Harlin’s megabomb, which entered Guinness for its flop-itude.
Aristocratic damsel with a feisty streak Matthew Modine, we guess
Respectable actor slumming it as a dastardly villain Frank Langella, who bellows “I love this! I love it!” during the battle at the end
Saltiest put-down “Since you lie so easily and since you are so shallow, I shall lie you in a shallow grave.”
Worth its weight in treasure? Heavens no. But the movie’s influence on the Pirates franchise is undeniable—note everything from the basic plot to the alternately rousing and waggish tone to the presence of an identical-looking, comic-relief monkey.