The 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.