Huge Jimmy Buffett fan here.
There is a show (documentary, biography? I don’t know) but I have seen it on CMT and it goes through Jimmy’s career with interviews with Jimmy peppered throughout.
Jimmy himself talks about the Parrotheads, saying he really doesn’t know where that part came from. He indicated in as nice a way as he could that he doesn’t “get it” about the parrot head hats and paraphanelia his fans come to his concerts with. However, he said, more power to them.
His shop in Margaritaville carries all that stuff but the parrotheads came first, and the businessman in Jimmy saw that he could capitalize on it. He reasoned that they’ve got to buy all those crazy hats and beach balls somewhere, so why not from Margaritaville!!!
He also talks about how he doesn’t party like he used to - and certainly not as his songs imply!
So he is basically a workaholic businessman/musician who knows how to write a helluva song!! At least that’s what I got out of the biography.
“…yes I am a pirate
born 200 years too late
the canons don’t thunder
there’s nothin’ to plunder
I’m an over 40 victim of fate…”