Born in Oklahoma and raised in the Washington, D.C., area, she began performing in her boyfriend (and future husband) Mas Palermo's band at the age of 16. Her powerhouse vocals were so popular with club audiences that soon the group was renamed Kelly & the Fireballs in her honor. After Willis graduated high school, the band moved to Austin, TX, only to break up six months later.
As a result, Willis began learning to play guitar while drummer Palermo honed his songwriting chops. The duo started a new band, Radio Ranch, with guitarist David Murray, steel player Michael Hardwick, and bassist Michael Foreman. One of Radio Ranch's performances so impressed singer Nanci Griffith that she began lobbying her label, MCA, to sign to group, leading to Willis' 1990 debut Well-Travelled Love.