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8. "Rime of the Ancient Mariner" - Iron Maiden
Every maritime journey should aspire to be epic, which is exactly what this legendary metal song by Iron Maiden is. With screaming high-pitched vocals, a lengthy breakdown that surpasses Spinal Tap's on "Stonehenge," and guitars that sound straight out of 8-bit Nintendo game Contra, the 13-plus minute "Rime" delivers a new musical twist on the classic sea-chantey, while staying true to the old themes: evil albatrosses, cursed sailors, phantom ships and "star-dogged moons."
7. "The Ballad of Patch Eye and Meg" - Michelle Shocked
This innocent, hushed busker's ballad from Michelle Shocked's Texas Campfire Tapes (recorded in 1986, directly to a walkman at the Kerville Folk Festival), tells the tale of a grey-haired, tattooed, peg-legged, patch-eyed ex-pirate who loves to recount his wild experiences, except for the story of his love affair with a brown-haired, blue-eyed girl named Meg.
6. "Pirate's Life" - The Vandals
What pirate Top 20 countdown playlist would be complete without a punk-rock song about an acid trip gone terribly wrong while riding Pirates of the Caribbean at Disneyland?
5. "40,000 Headmen" - Traffic
The pirate-y protagonist of this haunting Traffic tune follows three small ships to a distant shore, where he finds and steals the loot their crews have stashed. Little does he know as he lights out, the headmen are on his tail, ready for revenge and brandishing 20 shotguns each.


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