Heavily influenced by her mother, who used to sing in local musicals, Kelly became interested in music. One day during a high school visit to the beach, she entered a nearby pay recording booth and sang her own version of Elvis Presley's "Teddy Bear." With the demo in hand, Willis impressed her then boyfriend, drummer Mas Palermo, and joined his rockabilly band at the age of 16. The band took her on as the lead vocalist and soon rechristened the band Kelly Willis & the Fireballs. After Willis's high school graduation, the band decided to move to Austin, Texas, to participate in the vibrant Austin music scene. After a few months in Austin, however, the band broke up. Willis and Palermo, married in 1989, formed a new band called Radio Ranch. In Austin, Willis attracted the notice of several influential Texas singer-songwriters including Nanci Griffith and Lyle Lovett. Griffith introduced MCA producer Tony Brown to Willis. Brown was very impressed with Willis's vocal abilities and signed her to the MCA label in 1989.