The band, which formed while Elmore was attending law school, released two albums between the years of 2001 and 2006, both of which were met with generally positive reviews.

The Los Angeles Times gave the album 3.5 out of 4 stars, with reviewer Kevin Bronson saying that "[Elmore's] streaming anecdotes give the listener the feeling of walking right into the middle of life-altering events.

"[5] The College Music Journal's Amy Wan called the album a "showcase for Elmore's powerfully biting lyrics and her passionate voice, dancing deftly between little-girl sweet and outright roar,"[6] and The Village Voice gave the album an A−, with famed music journalist Robert Christgau praising the debut, saying that "Elmore left a great band to go to law school.

[8] Along with the performance agenda in 2003, Elmore balanced touring, songwriting for their next album, and a return to law school while the band suffered the loss of yet another drummer, as Espy was forced to leave after a tenure of nearly a year and a half for personal reasons.

[2] The band settled on their second permanent drummer, Steve Van Horn, shortly after Espy left following their round of touring.

[2] The sessions were difficult, with 14-hour recording days being balanced with Elmore attempting to finish remaining law school papers, combined with weekend tour jaunts to the East Coast.

"[12] Blender Magazine gave the album four stars, stating that "Elizabeth Elmore, a law-school graduate with boy trouble to match her student loans, writes songs that are as much legal briefs as diary entries.

[2] The band spent 2004 and 2005 touring the United States for over nine months, including opening slots for Ted Leo and the Pharmacists, The Killers, Modest Mouse, Death Cab for Cutie, and the Donnas.

They completed their summer tour with Stereo South bassist Greg Mytych,[8] and planned to record a new album in 2006, but came to a halt due to mitigating factors, including the issues with Lookout!

[16] Drummer Steve Van Horn has joined former Chicagoan and current Austin, TX based singer-songwriter Che Arthur's touring band.