12. Janis Ian
"Society's Child (Baby I've Been Thinking)" (1967, Number 14) and "At Seventeen" (1975, Number Three)
Protest records don't get much weirder than "Society's Child." Produced by "Shadow" Morton, best known for whipping up sonic frenzies on the Shangri-Las' street corner melodramas, this tale of thwarted interracial love, written and sung by 13-year-old Ian, is like Guess Who's Coming to Dinner? starring the Leader of the Pack. Eight years later, "At Seventeen," Ian's sour reminiscence of an adolescence marred by bad skin and getting "picked last for basketball," set a standard for sulk-pop that even our greatest goth whiners and grunge groaners have had difficulty matching.