In late 1986, Bill Retoff was playing Fender Jazz Bass for a cover band in Central Illinois when a group of art students happened to drop by one of their gigs one night. They asked him to play in the backup band they were assembling to play at a Monkees convention in Michigan the following summer. The band never actually materialized into a full-time pursuit, and the convention gig fell by the wayside, but they did spend a good amount of time rehearsing and auditioning, including two of the many songs Retoff had been writing on his own for years inspired by the great pop/rock bands of the 1960s. Besides giving him newfound confidence in his songwriting ability, it also opened his eyes to the burgeoning indie pop scene and gave him the impetus he needed to dive headfirst into that scene.
His first serious musical venture came as a member of the Insomniacs (which eventually morphed into the ensemble Retoff, McKenzie, Butler & Pierce) in the early '90s. Retoff formed his own label, Maize Records, specifically for the band, and between 1992 and 1994, they released two acclaimed (in underground pop circles) full-length cassettes and numerous singles. The band gradually disintegrated due in large part to the miles of travel between them. At about the exact moment of disintegration, Retoff was struck down by spinal meningitis and diagnosed with intestinal cancer. It nearly ended his life, but he ultimately recovered from the ordeal and eventually settled back into recording as a solo artist.
He released his debut solo album, Pop Jewelry, in 1996, along with a legion of 45s and made appearances on numerous compilations. He played with the band Eternal Groove, who released a single in 1997, and produced the sole effort by Billy Blastoff, the band that Dan McKenzie, Dave Butler, and Ed Pierce formed following Retoff, McKenzie, Butler & Pierce. Two of his songs were also covered by the semi-legendary '60s combo the E-Types on their 1998 reunion album Chase the Moon. Retoff's dedicated cult following continued to steadily grow, and a second solo album, Reanimation, appeared in 2000. That summer also saw him reconvene with McKenzie, Butler, and Pierce to begin recording all new material.