When Womack emerged as a contemporary country artist in 1997, her material resembled that of Dolly Parton and Tammy Wynette, except for the way Womack's music mixed an old-fashioned style with contemporary elements. Her 2000 album I Hope You Dance had an entirely different sound, using pop music elements instead of traditional country. It was not until the release of There's More Where That Came From in 2005 that Womack returned to recording traditional country music. After a hiatus in 2008, Womack returned in 2014 with a new album (The Way I'm Livin') and a new sound which blended country and Americana.
Womack has released a total of six studio albums and two compilations. Four of her studio albums have received a Gold certification or higher by the Recording Industry Association of America. Additionally, she has received five Academy of Country Music Awards, six Country Music Association Awards, and a Grammy Award. She has sold over 6 million albums worldwide. Womack is the wife of record producer Frank Liddell, and ex-wife of songwriter and musician Jason Sellers; her daughter with the latter, Aubrie Sellers, is also a country music artist.
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. Her mother was a schoolteacher and her father was also a high school principal. As a child, Womack studied the piano and later graduated from Jacksonville High School in 1984. After graduating, Womack attended South Plains Junior College in Levelland, Texas. The college was one of the first in the nation to offer country music degrees, and soon she became a member of the college band, Country Caravan. A year later, she left the college and after an agreement with her parents, Womack enrolled at Belmont University in Nashville, Tennessee, where she studied the commercial ways of the music business. In Nashville, she interned at the A&R department of MCA Records. She studied at the college until 1990, leaving the school a year before graduation.
Womack spent a few years raising her children before reentering the music business in the mid 90s. In 1995 she began performing her music in songwriting demos and at showcase concerts. At one of these showcase concerts, she was spotted by Tree Publishings, who signed her after listening to one of her original demo recordings. Womack wrote songs with some popular Nashville songwriters, including Bill Anderson and Ricky Skaggs, who recorded her composition, "I Don't Remember Forgetting" for one of his albums. After divorcing her first husband around that time, Womack decided to pursue a career as a country music artist. She auditioned for MCA chairman, Bruce Hinton, who praised her talents. Shortly afterward, she accepted a contract from MCA's sister record company, Decca Nashville in 1996.
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.