Libbi was raised in a musical environment. Her father was a trucker who moonlighted as a honky-tonk singer, and her mother worked at an area country music station. Libbi left home at the age of 16 to pursue a music education and career. 
In 1997, she released her debut album, Outskirts of You. That year she also reached a wide audience when in 1997 she made her singular appearance on the PBS music television program Austin City Limits which spotlighted some "Best of Austin" performers.