She briefly recorded songs with future Superchunk guitarist Mac McCaughan and others in a lo-fi band called Bricks and deejaying on the university's radio station, WKCR, until joining WFMU after her graduation in 1993.

Cantrell married Jeremy Tepper, the founder of Diesel Only Records and later programming director of Sirius XM radio station Outlaw Country, in 1997.

The album reached the attention of legendary UK DJ John Peel, who wrote of it, "[It is] my favourite record of the last ten years and possibly my life".

In August 2017, she began hosting Dark Horse Radio, a weekly 30-minute program on SiriusXM featuring the music of George Harrison.

[3] In the early part of her career, Cantrell combined her musical activities with a day job as a vice-president in the equity research department of Bank of America.