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Jimmy Buffett – A Pirate Looks at Forty Lyrics 7 years ago
I agree with two prior commenters - I understand that the bartender at The Chart Room was the subject, and perhaps the impetus, of the song.

In his pre-song monologue from 'You Had to be There', Jimmy spoke of a friend down in Key West who could not bring himself to hold down a regular job and, instead, turned to smuggling.

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Jimmy Buffett – Twelve Volt Man Lyrics 12 years ago
"...It's also supposedly one of Jimmy's favorite songs". I heard that also. Certainly one of my faves, from a time when more of Jimmy's songs seemed to be about the unique people encountered in his travels. For a kid growing up in New England (where attitudes tend to be super-conservative and the weather often ranges from cool to cold), songs like this speak of another, warmer place.

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Jimmy Buffett – Cowboy In The Jungle Lyrics 12 years ago
Not too difficult to figure out - this is a song for those who find themselves in unplanned places or circumstances. Like so many of Jimmy's songs, this song is a vehicle to convey life advice. The advice here is to "Roll with the punches; play all of your hunches. Make the best of whatever comes your way. Forget that blind ambition, and learn to trust your intuition, plowin' straight ahead, come what may". (Stay loose, do what you think is right, and keep going).

The second part of the song is also typical Buffett fare; something that he does so well: Here, Jimmy throws a sarcastic light on the downside of folks from up north, heading to the Caribbean ("While American women in muumuus
Talk about all the things they did today. And their husbands quack about fishing
As they slug those rum drinks down; Discussing who caught what
and who sat on his butt...").

Finally, we get a little taste of what the quiet times in Jimmy's life are like, or maybe were like, before his music took off ("Alone on a midnight passage
I can count the falling stars. While the Southern Cross and the satellites
They remind me of where we are...").

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