Early years: 1997–1999 Womack released her
self-titled debut album on Decca in May 1997. This was also her first to be produced by the label's then-senior vice president and frequent songwriting collaborator
Mark Wright, best known for his work with
Gary Allan and
Mark Chesnutt. while Chesnutt collaborated with Womack on the track "Make Memories with Me". It led to the release of the album's second single, "
The Fool" shortly afterward. More successful than her first single, "The Fool" peaked at number two on the country charts. It was later followed by "
You've Got to Talk to Me" and "
Buckaroo", respectively charting at number 2 and number 27. 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." Thom Owens of
AllMusic thought Wright's production was "slick [and] professional" and noted that Womack "certainly has a voice that can make the mediocre sound appealing, which results in a winning debut." 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. The
Country Music Association nominated her for the Horizon Award between 1997 and 1998. Womack's second and final Decca release was 1998's
Some Things I Know, which was also produced by Wright. They were followed by "
(Now You See Me) Now You Don't" and a cover of
Buddy Miller's "
Don't Tell Me".
Pop crossover success: 2000–2004 Womack's first MCA studio album and third overall was 2000's
I Hope You Dance which met with major success. Contributing songwriters to
I Hope You Dance once again included Womack, Sellers, and Miller; another contributing writer was
Lonesome River Band member
Ronnie Bowman. The album produced a total of four singles, which made the Top 40 on the
Billboard country singles charts. The album was led off by the single "
I Hope You Dance", a collaboration with the country music band
Sons of the Desert. It became the most successful single off the album with a number 1 peak on the
Billboard country singles chart and a number 14 peak on the
Hot 100 charts, representing Womack's and Sons of the Desert's highest peaks on those charts. In 2002,
I Hope You Dance was certified triple-platinum by the RIAA for shipments of 3 million copies. In August 2002, MCA released Womack's fourth studio album,
Something Worth Leaving Behind. It was led off by the single "
Something Worth Leaving Behind", which charted at 20 on Hot Country Songs. David Cantwell of
No Depression said "The results, no matter which side of the pop-twang divide you're on, will likely be very disappointing." Conversely,
Stephen Thomas Erlewine of
AllMusic thought the album "was a sure fit for Womack to move into the country mainstream for good." Womack told Mario Tarradell of
The Dallas Morning News in 2005, "I tried...to please everybody with that record...myself, radio, the listeners, everybody who loved 'Never Again, Again' and everybody who loved 'I Hope You Dance.' And it just didn't work. It backfired." That September, Womack contributed to the theme song for the PBS animated TV series adaptation of
The Berenstain Bears. One month later, she released her first Christmas album,
The Season for Romance; among this album's new songs were the title track and "Forever Christmas Eve". She also collaborated with
Willie Nelson on his single, "Mendocino County Line," which peaked at 22 on Hot Country Songs. The single won a Grammy and Country Music award that year. In early 2003, she played Haylie Adams in a guest appearance on the
CBS television series
The District. She also collaborated with Red Dirt Music band
Cross Canadian Ragweed on their hit "Sick and Tired" in 2004. Also that year, she released her first
Greatest Hits compilation, which included two new songs; "The Wrong Girl" and "Time for Me to Go", the former released as a single. Erlewine praised the album's production and songs, comparing it to those released by
Loretta Lynn,
Barbara Mandrell, and
Dolly Parton in the 1970s. He would later say it was "not only the best album that Lee Ann Womack has yet made, but one that does suggest that there is indeed more where this came from." The lead single, "
I May Hate Myself in the Morning" was a Top 10 hit in 2005, and also won "Single of the Year" by the CMA later that year. The album was rescheduled into 2007, because Womack found more songs that she wanted to record, however it was never released and Womack left Mercury in favor of MCA. Also in 2007, Womack collaborated with
Joe Nichols on "If I Could Only Fly" from his album
Real Things and recorded
Steve Dorff's "Love Will Still Be There" for the soundtrack of the film
September Dawn. Womack's sixth studio album and last for MCA,
Call Me Crazy, was released on October 21, 2008. The album, released on vinyl and CD, produced by
Tony Brown; it has been described as a dark album with plenty of songs about drinking and losing love. Womack co-wrote four of the album's 12 songs.
Call Me Crazy charted only two singles in the United States: "
Last Call" and "
Solitary Thinkin'", which reached top 40 on Hot Country Songs. At the
51st Annual Grammy Awards in 2009, "Last Call" was nominated for Best Female Country Vocal Performance; one year later,
Call Me Crazy was also nominated for Best Country Album, with "Everything But Quits" and "Solitary Thinkin'" being Womack's final nominations for Best Country Collaboration with Vocals and Best Female Country Vocal Performance, respectively. In October 2010, Womack recorded "Liars Lie" for the
soundtrack of the film
Country Strong. Womack also collaborated with Alan Jackson on a cover of
Johnny Cash's "
Ring of Fire", which was released that December as a single from his compilation album,
34 Number Ones. His version of the song was a minor hit, charting to number 45 on Hot Country Songs. Though Womack is featured on the song, she was not given credit on the charts. In August 2012, Womack announced her departure from MCA Nashville.
Americana transition and return to music: 2014–present In April 2014, Womack signed with
Sugar Hill Records, an imprint of Rounder Records. Her first album for the label, ''
The Way I'm Livin''', was released September 23, 2014. Erlewine said that the album "plays like a classic album: it's a record where the sum is greater than the individual parts". Her second album for Sugar Hill, a vinyl
extended play album of cover songs called
Trouble in Mind, was released in 2015. At the
57th Annual Grammy Awards that year, ''The Way I'm Livin'
was nominated for Best Country Album; one year later, "Chances Are" was also nominated for Best Country Solo Performance. and her first CMA Female Vocalist of the Year nomination in ten years. Ahead of her 2015 tour in support of The Way I'm Livin''', Womack appeared at the
C2C: Country to Country festival in the UK. On August 15, 2017, Womack announced her new album
The Lonely, the Lonesome & the Gone, which was released on October 27 through
ATO Records. The project included 14 songs that were recorded largely at
SugarHill Recording Studios in
Houston, Texas.
The Lonely, the Lonesome & the Gone and "All the Trouble" received Grammy Award nominations for Best Americana Album and Best American Roots Song, respectively, in 2019. ==Personal life==