Russ... You don't have to play Jimmy Buffett songs like Jimmy does them!

I don't know if you have heard it, but the great jazz guitarist Charlie Hunter put an album out a few years ago that was the entire Natty Dread album by Bob Marley, but COMPLETELY reversioned... Not a trace of reggae in the arrangements at all.

Sometimes it is a load of fun to take songs by a hated singer, and just twist them until they fit YOU, and can barely be recognized by the fans. But at least when they request something (or you just want to flummox them), you've got a bullet in the barrel.
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An arranger is just a tool. What matters is what you build with it..!