After the dissolution of alt-country kings Whiskeytown, frontman Ryan Adams' solo career received the bulk of critical attention. Nevertheless, vocalist/fiddle player Caitlin Cary was waiting in the wings with her own impressive batch of music. Cary released a solo EP, Waltzie (Yep Roc), in 2000. The release was a stripped-down, folky affair and included a stirring take on Richard Thompson's Withered and Died. Her debut full-length, the more fully realized While You Weren't Looking (Yep Roc), came out in March of 2002, boasting a wider sonic pallet and a host of rock, pop, and country influences. Jangle pop legend Chris Stamey produced the effort and Whiskeytown alumni Mike Daly and Skillet Gilmore (who happened to be Cary's husband) helped out. Also on hand were Mitch Easter, Superchunk's Jon Wurster, and Jen Gunderman (the Jayhawks), among others. Three tracks were co-written by Ryan Adams, who also did a vocal turn on the four-song bonus disc. Most of the crew from While You Weren't Looking returned for Cary's equaly splendid second album, I'm Staying Out, which also featured contributions from Mary Chapin Carpenter and Don Dixon. She released Begonias, a collaboration with Thad Cockrell issued by Yep Roc, in the summer of 2005.

Cary grew up in Seville, OH, to a musical family. She started playing violin at a young age and found an early muse in a tape of songs, including Tennessee Stud and Mr. Spaceman, that her musician brother sent back from Alaska. Cary's violin playing lapsed as a teen, but she picked the instrument up again while working on an English degree at Ohio's College of Wooster. After dabbling in performing, she enrolled in North Carolina State's MFA program in creative writing. However, her studies were postponed when, through a friend, Adams found out that Cary played fiddle. The two would go on to front the dynamic country rockers, serving as a sort of '90s Gram Parsons and Emmylou Harris. Whiskeytown began dissolving in the late '90s, while the group's final album, Pneumonia, suffered repeated delays. Cary had begun writing songs with guitarist Mike Daly while the two were still touring with Whiskeytown. After witnessing performances by Sheryl Crow and Gillian Welch at the taping of the #Sessions at West 54th tribute to Gram Parsons (at which Whiskeytown also performed), Cary made a conscious decision to pursue a solo career. ~ Erik Hage, Rovi