Born and raised in Jacksonville, TX, Womack became infatuated with music at an early age, which is appropriate for the daughter of a disc jockey. Her father often took her to work, where she picked out records to play on the air. Following high school graduation, she attended South Plains Junior College in Levelland, TX. The school was one of the first in the country to offer degrees in country and bluegrass music, and Womack soon became a member of the college's band, Country Caravan. She traveled throughout the South and California with Country Caravan and stayed with the group until she left South Plains to study music business at Belmont University in Nashville. That led to an internship in MCA's A&R department.

By 1990, she had settled in Nashville, where she married and became a mother. She continued to attend Belmont, as well as write songs. Soon, she began singing on songwriting demos and performing her own showcase concerts. Eventually, Womack was spotted by Tree Publishing at one of her showcases. In 1995, the company signed her after listening to one of her original demos. While she was a staff writer at Tree, she co-wrote songs with Ed Hill, Bill Anderson, Sam Hogin, and Mark Wright. Her songs were recorded by Anderson and Ricky Skaggs.

Within a year after signing to Tree, Lee Ann Womack signed to Decca Records as a recording artist. Wright was hired as the producer for Womack's debut album, which was comprised of both original material and songs written by professional songwriters. Mark Chesnutt, Ricky Skaggs, Sharon White, and Tony Brown all appeared on the record, which created a buzz in the industry.