“A Pirate Looks at Forty” by Jimmy Buffett

"A Pirate Looks at Forty" first turned up on A1A, Jimmy Buffett's 1974 album for Dunhill, and it's Buffett's song through and through, words and music, with Don Gant producing. He wrote it about Phillip Clark, and it traces back to the Chart Room, the spot where Buffett first performed after moving to Key West, Florida. The song is a rueful confession from a modern-day drug smuggler, washed up at forty, sorry that the pirate's life was long gone before he was born and wondering what comes next.

Cash Box heard an almost-reggae feel in the chord progression and liked the guitar work. For the single, the fourth verse was cut to suit radio. It became one of his better-loved songs, one of "The Big 8" he played at almost every show, always in the second set.

Written with AI assistance from RockLists chart data, MusicBrainz and Wikipedia.