In early 1995, after being in a few unfruitful band situations, the Toledo-based Jessica Bailiff borrowed a friend's 4-track cassette recorder and experimented with sounds and songs. After a few months, an obsession with creating on tape developed, and she bought one of her own. She sent a demo, upon the suggestion of a friend and mentor, Alan Sparhawk of Low, to the Chicago label, Kranky, who had just released Low's Songs For a Dead Pilot EP. Soon after, Jessica received a call from someone at Kranky, and the label released her album about eight months later.

Jessica's first album, Even in Silence, was released in June, 1998; its contents were recorded both on 4-track cassette and at low's studio, 20 Below, in Duluth, Minnesota. A second album, Hour of the Trace, was also released by Kranky (again, recorded and produced with Alan Sparhawk of Low) in October, 1999. A third, eponymous record, described by Bailiff as being about "...stagefright, dreams, loss of creative energy/desire, love & time, living in the same place all your life, ghosts, near-death experiences, etc...," was released in October of 2002.

In addition to her three solo albums, singles and compilation appearances have been realeased from 1999-present. Jessica has also recorded with friend Jesse Edwards (of Red Morning Chorus and the.dithering.effect) as Northern Song Dynasty, David Pearce (of Flying Saucer Attack) as Clear Horizon, and Rachel Goldstar as Eau Claire. She has appeared on recordings by Rivulets, Red Morning Chorus, Saturday Looks Good to Me, and the Elegy Radio Ensemble, and has toured with Charles Atlas, Yellow6, Drekka, Rivulets, and Low.

Reviews and interviews have appeared in Copper Press, Virago Violet, Alternative Press, Magnet, The Wire, Losing Today, The Brainwashed Brain, and fanzines worldwide.

Chris Nosal wrote in Philadelphia City Paper that "Bailiff merges the best of rock, folk and genuine sonic exploration into a loud and powerfuyl whisper."

David Keenan wrote in The Wire that "Bailiff has succeeded in creating a singular soundworld where frail, intensely personal wordage combines with hurricane sound."