Cailin Rose was previously the lead singer of Nashville indie band Save Macaulay, on local label Theory 8 until 2007. As a solo artist, she signed to BMI in 2008.The title track of her seven-track 2008 EP, Dead Flowers, is a cover of a Rolling Stones song.

Her first album, Own Side Now, was released by Names Records in August 2010. Her vocal performance and lyrics have led to comparisons to Loretta Lynn, Patsy Cline and Iris DeMent. Claire Suddath of Time magazine named Own Side Now one of the Top 10 Albums of 2011, ranking it at No.

A new studio album titled The Stand-In was released on February 25, 2013.