She moved to Toronto in 1996, and quickly became a fixture at the city's open mikes. There she met Doc (real name: Martin McKinney), an engineer and producer, and the two began working on a demo featuring his programming and her vocals. Sony eventually took interest, and suddenly Esthero went from a fledgling idea to a duo with Esthero's name as their own and a record, Breath from Another, issued in spring 1998 on the label's Work imprint. Breath's mix of beats, lush vocals, and fractured bits of programmed samples caught on perfectly with the trip-hop trend of the time, and Esthero had success with singles like Heaven Sent and the hip-hop-flavored title track.

However, it would take nearly seven years for a follow-up to appear. In the interim Esthero parted ways with Doc and struck out on her own, contributing vocals to projects like Black Eyed Peas' "Weekends" (2000). Signing with Reprise, she began work on new material, and returned officially in summer 2004 with the club single O.G. Bitch. Esthero followed the single in November of that year with We R in Need of a Musical Revolution, an EP that found her collaborating with Sean Lennon, Cee-Lo, and producer James Robertson (Skye Sweetnam) on a 21st century version of Breath's assemblage sound. The EP set up a full-length entitled Wikked Lil' Girls, which was slated for release in early 2005. ~ Johnny Loftus