Melding hooky pop songs with the muscled approach of a rock band, Letters to Cleo formed in Boston in 1990. Guitarist Greg McKenna actually started Letters to Cleo as another group; when he began searching for a background singer to complete his lineup, he found Kay Hanley. A powerhouse vocalist who had previously performed in a local new wave group, Hanley remained with McKenna after the original band fell apart several months later. The band adopted a peppy power pop sound as well as a new name, Letters to Cleo, which made reference to a pen pal with whom Hanley had corresponded during her childhood. Guitarist Michael Eisenstien (whom Hanley would later marry), drummer Stacy Jones, and bassist Scott Reibling soon completed the lineup, and the quintet spent several years touring the Boston circuit.