The group was formed by Cyco, then known as Psycho (born Andrew "Drew" Holiman), after he was hired as a disc jockey at a Los Angeles radio station. With members DJ Streek and Shakespear the One-Man Riot, Insane Poetry released its debut single, "Twelve Strokes Till Midnight," in 1988. After replacing Shakespear with Em-Dee, Insane Poetry signed with Nastymix/Ichiban Records through an association with emcee Rodney O and released its debut album, Grim Reality, in 1992, which peaked at #98 on the Billboard Top R&B/Hip-Hop Albums chart. After Nastymix went out of business, Insane Poetry signed with independent React Records, which released its second album, Blacc Plague, in 1996, but disagreements over promotion and support led the group to leave the label. In 1998, Cyco appeared on Vanilla