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Womack was born and raised in Jacksonville, Texas. At an early age, she was interested in country music. Her father, a disc jockey, often took his daughter to work with him to help choose records to play on the air. Womack was the second of two daughters.

Womack released her self-titled debut album in May 1997, produced by Mark Wright. The album consisted of self-penned material as well as songs written by other artists, including Mark Chesnutt, Ricky Skaggs, and Sharon White. The first single, "Never Again, Again" made the country charts and playlists by March 1997, which led to the release of the album's second single, "The Fool" shortly afterward. More successful than her first single, "The Fool" reached the Top 5 on the Billboard Country chart that year. That year she won major awards from the country music community; Top New Female Vocalist from the Academy of Country Music Awards, Top Artist of the Year from Billboard Magazine, and was nominated for the Horizon award by the Country Music Association. Decca Nashville decided to close its doors in 1998, moving Womack to MCA Nashville Records that year.  In 1998, Womack released her second studio album, Some Things I Know, which was also produced by Wright. The album's first two singles, "A Little Past Little Rock" and "I'll Think of a Reason Later" both went to No. 2 on the Billboard Country Chart. Two additional singles, "(Now You See Me) Now You Don't" and "Don't Tell Me" were released in 1999, and the album was certified Gold by the RIAA soon after.  That year, she also won Favorite Country New Artist from the American Music Awards. Womack also contributed her vocals to the songs "If You're Ever Down in Dallas" and "The Man Who Made Mama Cry" in collaboration with her ex-husband and musician, Jason Sellers. The material was promoted through shows through October to November before the birth of Womack's second child in January 1999.
Lee Ann Womack