Devoted fans—affectionately dubbed Parrot Heads—find escapism in Jimmy Buffett's ballads, vicariously experiencing through his strongly autobiographical songs Buffett's life of beaches, bars, and boats. Yet Buffett's life has been far more than rum-soaked nights and afternoon naps in beachside hammocks. Even though Buffett relishes his image of "the professional misfit," this millionaire "beach bum" is actually an ambitious and clever entrepreneur.

Born on Christmas Day, 1946 in Pascagoula, Mississippi, Jimmy Buffett spent most of his youth in the Catholic school system in Mobile, Alabama. During college he learned to play the guitar and started singing in clubs. While attending the University of Southern Mississippi, about 80 miles from New Orleans, Buffett played regularly at the Bayou Room on Bourbon Street. Once he had a taste of performing, his life course was set. Even though he married and took a job at the Mobile shipyards...