Folks in her native Chicago also know the talented singer/songwriter as a bartender, a midwife's assistant, and an ordained reverend. O'Connor's incredibly diverse life began in Chicago as a first-generation Irish-American with a father who would teach her all the Irish classics. She first came to the alternative country crowd's attention in 1994 when she joined the Blacks. She took a break from the band in 1996 and released her first solo album, Cerulean Blue, by herself in the spring. In 1998 the Blacks made their debut on record with Dolly Horrorshow on Bloodshot, which happened to be released the same day as I Wanna Be Kate, a Chicago-based tribute album in honor of Kate Bush featuring O'Connor's version of "The Saxophone Song." By 2000 the Blacks had run out of steam, but O'Connor was an in-demand guest vocalist, often spending time in Andrew Bird's band. By 2004 she was ready to strike out on her own again, and Bloodshot couldn't have been happier. The label signed its old friend and released her Til the Dawn in August of that year. ~ David Jeffries