When swamp pop singer Joe Barry finally lost his battle to numerous health problems and passed away in August 2004 he’d lived so many different lives it was hard to tell where one started and the other left off.

His 1961 smash “I’m A Fool to Care” rocketed him to a decade of stardom studded with heights he’d never imagined and lows that he’d never forget. A whirlwind of silk suits, American Bandstand appearances, rip-off record deals and trashed hotel rooms—and the drugs and booze...