I wrote this for an old friend of mine a few years back who could just not seem to find his occupation in the twentieth century, so he just chose to live in a fantasy world. And then I looked at him [and] I went, well what the hell's wrong with that?
I'll be the first to admit I'm not really a Jimmy Buffett fan, though you gotta admire a guy who has figured out how to make a way of life out of wearing hawaiian shirts and drinking frozen blender drinks on some warm tropical beach. But there's something absolutely universal about this modern pirate's midlife crisis that always gets to me. Maybe it's because I'm getting old myself. Like Buffett's narrator, I'm a far cry from the man of potential I once was; like him, I often feel that my talents would have been better applied, and my urges better served, in a world which had already passed by the time I was born.
That the song delivers its autobiography with no stronger tone than a faint whiff of bittersweet is pure easygoing Buffett; its shrug of beach-resort regret models for us an acceptance of the world-as-it-is which is, if still not exactly what we hoped for, at least free of stress, and still sweet under its little paper umbrella. Meanwhile, surfer Jack Johnson's cover of the song 30 years later is hushed, and more introspective, with a perfect bowed cello undertone like the sea itself; Johnson is younger, but you can hear it: he knows, too, the way the subjective world of what-could-be shrinks as we grow old.