So, considering that “Fifteen Men on a Dead Man's Chest” is not an actual pirate song, are there any surviving examples of the genuine article? The answer is yes. This ballad is called “The Flying Cloud” and it was sung widely among both sailors and lumberjacks in the 19^th century.

It purports to be from the mouth of a slaver and pirate as he awaits his execution for his many crimes, and tells the story of his misspent life. Beginning as a young Irishman looking to make his fortune, he ships out on a slaving voyage that later turns to piracy. After many pirate attacks and many murders, the pirates are brought to heel. Defeated in a bloody shipboard fight, they are hauled back to face trial and then condemned to hang.

Mournfully, the doomed pirate thinks back over the slaves he took and how terribly they were mistreated, the murders he participated in, and his wasted life. He concludes that it was strong drink and the desire for an easy living that led him to the gallows, and bids farewell to his lost love back in Dublin. The Flying Cloud is a harrowing anti-slavery song as well as a moralizing “don't run off and become a pirate” piece. What distinguishes it from “Fifteen Men On a Dead Man's Chest” is that it's a genuine folk song, sung by real sailors and probably even by real pirates. It may even have been written by a real pirate who was about to be hanged, although no one can say for sure.