Originally from Lawton, Oklahoma, the youngest of three children, Kelly Willis grew up mostly in North Carolina and Virginia. She has mentioned in interviews that her mother was involved in musicals when Kelly was a child and that could have been the starting point for her own interest in singing.

That interest turned into something more substantial when in high school she went to the beach, got into one of those pay recording booths, and belted out "Teddy Bear" a song made famous by Elvis Presley. Demo tape in hand she managed to get into her boyfriend's rockabilly band. With influences ranging from Patsy Cline, Wanda Jackson, the Blasters, the Tail Gators and the Leroi Brothers, Kelly and the Fireballs were a band whose popularity around the D.C. area was rising fast when in the late '80's , they decided to move to Austin, Texas.

It did not take long for Kelly to get noticed in Austin, One night while playing the Continental Club, Nanci Griffith wandered in near the end of the set. After hearing Kelly sing, Griffith headed for the phone and dialed MCA producer Tony Brown, who had signed Griffith as well as Lyle Lovett and Steve Earle. A few months later, a record deal was done and work on her debut album "Well Traveled Love" began.

Kelly released three albums for MCA and was signed to A&M Records until leaving the label in January 1997 . She has taken the last five years and used them to write songs and take control of her career. Her first release since 1993, a 4 song EP called "Fading Fast" released on A&M Records in 1996, gave her fans a good indication where Kelly's heading musically. Kelly began 1998 with a new full-length CD completed, and signed a deal with Rykodisc over that summer to release it. In February of 1999, the CD "What I Deserve" was released on Rykodisc to rave reviews.