Though she didn’t begin her musical career until relatively late, Deana Carter managed to defy conventional expectations and unexpectedly shot to the top of the country charts upon the release of her 1996 debut, Did I Shave My Legs for This? Carter’s success was equally unexpected considering that she didn’t quite fit into the mold of a standard female contemporary country singer. Melding the popular appeal of country chanteuses with folky singer/songwriters like Mary Chapin Carpenter, Carter racked up both positive reviews and healthy sales with Did I Shave My Legs for This?, becoming one of the most pleasant success stories of the post-Garth Brooks generation.

As the daughter of Nashville studio guitarist Fred Carter, Jr., Deana Carter grew up in a musical environment, and was exposed to a wide variety of music. Fred played guitar for a wide variety of musicians, including Willie Nelson, Bob Dylan, Waylon Jennings, and Simon & Garfunkel. The music of those artists would eventually seep into Deana’s own style, which she hadn’t yet formed when she initially tried to land a record contract at the age of 17. Despite her efforts and her father’s assistance, Carter wasn’t able to secure a deal, so she abandoned music to study nursing at the University of Tennessee. While she was a student, she continued to sing for fun, yet she didn’t devote much energy to music.