She has released a series of well-regarded solo albums, and has either toured or played with Wilco, the Indigo Girls, Feist, Yo La Tengo, Dump, and the Mountain Goats, among other bands and musicians.
The most enjoyable and useful job she landed was working in the publicity office at the well-known music venue/record label the Knitting Factory.
Reviewing the disc, Time Out New York wrote: "O'Connor is another Liz Phair or Elliott Smith waiting to happen" and praised her "understated guitar-based songs" and "matter of fact lyrics.
Her Matador debut, Over the Mountain, Across the Valley and Back to the Stars, was written in the aftermath of a personally difficult year, during which, among other things, she lost her older sister to brain cancer.
Spin wrote that her "unflinching lyrics and stunningly strong voice leap from distressing folk ballads to buzzing rock with ease.
She has never actively sought a lesbian audience, however, telling the web site AfterEllen.com: "I think I have avoided it in some ways, literally", while adding, "I mean, I'm gay and I'm completely comfortable with that, but it's never been a thing that's been related to what I do musically.
O'Connor felt burned out and discouraged,[12] and went back to working odd jobs around New York, including bartending on Broadway.
[12] In the fall of 2013, a song O'Connor co-wrote called "Running Blues" was premiered on the FX biker drama Sons of Anarchy.