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Womack released her [[Lee Ann Womack (album)|self-titled debut album]] on Decca in May 1997. This was also her first album to be produced by frequent songwriting collaborator [[Mark Wright (record producer)|Mark Wright]], best known for his work with [[Gary Allan]] and [[Amy Grant]]. The album consisted of self-penned material as well as songs written by other artists, including [[Mark Chesnutt]], Ricky Skaggs, and [[Sharon White (singer)|Sharon White]]; Skaggs and White sang backing vocals on "Never Again, Again"<ref>{{cite web|url=https://thebluegrasssituation.com/read/hangin-sangin-lee-ann-womack/|title=Hangin' & Sangin': Lee Ann Womack|last=McCarney|first=Kelly|website=The Bluegrass Situation|date=October 31, 2017|accessdate=July 4, 2024|archive-date=February 29, 2024|archive-url=https://web.archive.org/web/20240229155302/https://thebluegrasssituation.com/read/hangin-sangin-lee-ann-womack/|url-status=live}}</ref> while Chesnutt collaborated with Womack on the track "Make Memories with Me".<ref name="allmusic"/> The first single, "[[Never Again, Again]]" made the top 40 on the ''[[Billboard (magazine)|Billboard]]'' [[Hot Country Songs]] and playlists by March 1997, which led to the release of the album's second single, "[[The Fool (Lee Ann Womack song)|The Fool]]" shortly afterward. More successful than her first single, "The Fool" reached the Top 5 on the Billboard Country chart that year. It was later followed by "[[You've Got to Talk to Me]]" and "[[Buckaroo (song)|Buckaroo]]". Rating the album "A", [[Alanna Nash]] of ''[[Entertainment Weekly]]'' wrote that "This native of Jacksonville, Tex., has more heart than any other new female country singer, and a passel of traditional-sounding songs that may just be good enough to turn Nashville's commercial tide."<ref name="nash law">{{cite web|last=Nash|first=Alanna|url=https://ew.com/article/1997/05/16/lee-ann-womack/|title=''Lee Ann Womack''|publisher=Entertainment Weekly|date=May 16, 1997|accessdate=July 7, 2024|archive-date=July 8, 2024|archive-url=https://web.archive.org/web/20240708150219/https://ew.com/article/1997/05/16/lee-ann-womack/|url-status=live}}</ref> Thom Owens of [[AllMusic]] wrote that "[Wright's] slick, professional production helps make this self-titled album a pleasant listen, despite the fairly uneven songwriting, and Womack certainly has a voice that can make the mediocre sound appealing, which results in a winning debut."<ref name="owens law">{{cite web|title=''Lee Ann Womack'' review|last=Owens|first=Thom|url=https://www.allmusic.com/album/lee-ann-womack-mw0000019507|work=AllMusic|publisher=All Media Network|access-date=July 7, 2024|archive-date=October 11, 2023|archive-url=https://web.archive.org/web/20231011212944/https://www.allmusic.com/album/lee-ann-womack-mw0000019507|url-status=live}}</ref> The album's commercial success also led to the first of several industry award nominations for Womack. The [[Academy of Country Music]] awarded her as Top New Female Vocalist.<ref name="ACM">{{cite web|url=https://www.acmcountry.com/winners?awardTitle=Lee+Ann+Womack&awardCategory=&awardYear=&actionButton=Submit|title=Search results for Lee Ann Womack|publisher=Academy of Country Music|accessdate=June 17, 2024}}</ref> The [[Country Music Association]] nominated her for the Horizon Award between 1997 and 1998.<ref name="CMA">{{cite web|url=https://cmaawards.com/past-winners-and-nominees/?appSession=328JN186W75JW8II074I5SRGF8AL19GJ9KM3AY34IBE1O42UPH876OV815J7PY6QALKJ729ZAQ834GNMV19A162H558076BYU1Q2GU425V6MY83Q6D4OC60JY8D2U22K|title=Search results for Lee Ann Womack|publisher=Country Music Association|access-date=July 10, 2024|archive-date=September 3, 2023|archive-url=https://web.archive.org/web/20230903105900/https://cmaawards.com/past-winners-and-nominees/?appSession=328JN186W75JW8II074I5SRGF8AL19GJ9KM3AY34IBE1O42UPH876OV815J7PY6QALKJ729ZAQ834GNMV19A162H558076BYU1Q2GU425V6MY83Q6D4OC60JY8D2U22K|url-status=live}}</ref>
Womack's next Decca release was 1998's ''[[Some Things I Know]]'', which was also produced by Wright.<ref name="oldies"/> 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 album produced a total of four singles, three of which made the Top 40 on the ''Billboard'' country singles charts.
===Pop crossover success: 2000–2004===
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