Some within the industry wanted Lee Ann Womack to change her name. Womack signed her first recording contract in 1996 and release her first album (self-titled) in 1997. Around this time there was another "Lee Ann" (although spelled a bit differently) heating up the charts. Womack declined the suggestion believing country music fans could differentiate between her and teenage songbird LeAnn Rimes. The elder Lee Ann was right. Her debut album cracked the top ten of the country music charts and two of its singles peaked at number two.
After a decent sophomore effort in 1998 (Some Things I Know) she issued her seminal album, I Hope You Dance (2000). The title track of that record went to number one, became a huge crossover hit, and garnered Womack several major awards. It also helped to sell a bunch of Lee Ann Womack tickets. The song was so popular that she performed it at the 2000 Nobel Peace Prize concert. Womack's next album, 2002's Something Worth Leaving Behind, heard the Texan vocalist veer towards pop country. The album didn't sell well. Womack returned to her country roots in 2005 with There's More Where That Came From as well as 2008's Call Me Crazy.