100 Greatest Women, #16: Lee Ann Womack

100 Greatest Women: 10th Anniversary Edition


Lee Ann Womack

2008 Edition: #33 (+17)

When she released her debut album in 1997, she was widely hailed as the great hope for traditional country music, a much-needed counterpoint to the pop crossover sounds that were beginning to dominate the genre. With time, Womack would prove that she wasn’t so easy to pigeonhole.

She grew up in Texas, the daughter of a country radio disc jockey. Her dad turned her on to the sounds of classic country music and she was smitten. When the time came for college, she attended South Plains Junior College in Texas, since it was the only school she could find that offered a major in country music. She took the next logical step and moved to Nashville after that, attending Belmont University for a brief time.

While at the school, she interned at MCA Records. She was a dedicated follower of George Strait, and it was his label where she wanted to record. By the early nineties, she had settled down in Nashville with a husband and young child, while building up her songwriting catalog and putting on showcases. Tree Publishing caught a showcase, heard her demo and signed her. She scored some cuts on albums by Bill Anderson and Ricky Skaggs, but her stint as a staff writer was short-lived. Decca, an imprint of MCA, signed her to her own recording contract, and she started work on her debut album.

By the time it was ready for release in the spring of 1997, the biggest female artists in country music were pop-country superstar Shania Twain and teenage phenom LeAnn Rimes. While Rimes had flirted with classic country on her debut single “Blue,” Womack reveled in it on her entire debut album. The eponymous set featured guest appearances by Ricky Skaggs, Mark Chesnutt and The Whites. The lead single “Never Again, Again” topped out at No. 22, but record buyers hungry for traditional country made her album an instant hit, reaching the top ten within weeks of release. Radio jumped on the next two singles, “The Fool” and “You’ve Got to Talk To Me.” The album went platinum, the CMA nominated her twice for the Horizon Award and, in 1998, the ACM named her Top New Female Vocalist.

She kept the momentum going with her sophomore set, Some Things I Know, in 1998. The gold-selling disc produced another pair of top five hits, including “A Little Past Little Rock,” which netted Womack her first Grammy nomination. But her big breakthrough came with the lead single and title cut from her third disc, “I Hope You Dance.”

Almost instantly, the tender wish list became an anthem, a mother’s day classic and a graduation staple. It topped the country chart, crossed over to pop and AC, and earned her a slew of awards, including three ACM’s and a CMA in 2000. On the strength of “Dance,” “Ashes By Now,” and “Why They Call it Falling,” Womack was named CMA Female Vocalist of the Year in 2001. The album would eventually sell three million copies.

In 2002, Womack had the opportunity to sing with one of her childhood idols, dueting with Willie Nelson on “Mendicino County Line.” The song was a top twenty hit, and won both the ACM and CMA for Vocal Event, and a Grammy for Best Country Collaboration with Vocals. That same year, Womack released her ambitious fourth album, Something Worth Leaving Behind. It featured more challenging and off-beat material than she’d done before, along with a pop-flavored production that disappointed her purist fans. While radio didn’t embrace the project, the album went gold and the title track earned her another Grammy nomination.

Changes at her label and disappointment with the response to Behind led Womack to take her time working on her next project. She was unsure of which direction to go in until her husband played her the demo of a song he’d heard at work that day, “I’m Gonna Love You Tonight.” Her mouth dropped open when she heard the chorus, and she suddenly knew what direction her next project would go in. The song was chosen as the lead single, and retitled “I May Hate Myself in the Morning” to draw more attention to the money line in the chorus.

The song struck a deep chord with country listeners, and her album There’s More Where That Came From became her highest charting album to date when it entered at #12 on the Billboard 200. The ACM nominated her for Single and Album of the Year in the Spring of 2005, but the CMA went much further the following fall. Womack was the belle of the ball, winning Single and Album of the Year, along with Musical Event for her duet with her favorite singer, George Strait.

Womack released the stopgap single “Finding My Way Back Home” in 2006, which made its only album appearance on a European hits collection.  In 2008, Womack released her swan song for MCA Nashville, Call Me Crazy. It produced a top twenty hit with “Last Call” and another top forty hit with “Solitary Thinkin’,” both of which received Grammy nominations, along with the album itself.  After the single “There is a God” in 2009, Womack parted ways with MCA.

Far from ending her career, the label change was a rebirth, as Womack resurfaced on Sugar Hill Records and reemerged as a prominent, critically acclaimed Americana artist. Womack released The Way I’m Livin’ in 2014, and on the strength of that project, received multiple Grammy and Americana award nominations.  It also powered her to a CMA Female Vocalist nomination in 2015, her first in ten years.  In 2017, another critically acclaimed album followed. The Lonely, the Lonesome & the Gone was released on ATO Records, and its lead single, “All the Trouble,” is nominated for Song of the Year at the Americana awards. It is the first time in her storied career that Womack has received an industry nomination for her songwriting.

Essential Singles

  • Never Again, Again, 1997
  • The Fool, 1997
  • A Little Past Little Rock, 1998
  • I Hope You Dance (with Sons of the Desert), 2000
  • Mendicino County Line (with Willie Nelson), 2002
  • Something Worth Leaving Behind, 2002
  • I May Hate Myself in the Morning, 2004
  • Last Call, 2008
  • The Way I’m Livin’, 2014
  • All the Trouble, 2017

Essential Albums

  • I Hope You Dance, 2000
  • Something Worth Leaving Behind, 2002
  • There’s More Where That Came From, 2005
  • Call Me Crazy, 2008
  • The Way I’m Livin’, 2014
  • The Lonely, the Lonesome, & the Gone, 2017

Industry Awards

  • Academy of Country Music Awards
    • Single of the Year
      • I Hope You Dance (with Sons of the Desert), 2001
    • Song of the Year
      • I Hope You Dance, 2001
    • Vocal Event of the Year
      • I Hope You Dance (with Sons of the Desert), 2001
      • Mendicino County Line (with Willie Nelson), 2003
    • Top New Female Vocalist, 1998
  • Country Music Association Awards
    • Album of the Year
      • There’s More Where That Came From, 2005
    • Female Vocalist of the Year, 2001
    • Single of the Year
      • I Hope You Dance, 2000
      • I May Hate Myself in the Morning, 2005
    • Vocal Event of the Year
      • Mendicino County Line (with Willie Nelson), 2002
      • Good News, Bad News (with George Strait), 2005
  • Grammy Awards
    • Best Country Collaboration with Vocals
      • Mendicino County Line (with Willie Nelson), 2003

100 Greatest Women: 10th Anniversary Edition

Next: #15. Shania Twain

Previous: #17. Barbara Mandrell


  1. Lee Ann is one of my all favorite county artists ever. IMO, she is one of the few country who never dipped off in quality and gotten even more better has time went on. Lee Ann’s vocals is full of warmth and it’s a authentic country voice. She has a amazing catalog. I Hope You Dance and There’s More Where That Came From are classic albums, Something Worth Leaving Behind is a criminally underrated album, and Call Me Crazy, The Way I’m Livin, and The Lonely, the Lonesome, & the Gone are amazing albums. The irony is for a artist who has stay loyal to her country roots for most of her career, her biggest and one her best songs ever happen to be a pop-country track. I Hope You Dance is one of the greatest crossover country songs ever. I love Lee Ann’s voice on it and the song’s meaning has multiple ones. But, me listening to it recently I got the oblivious meaning it’s about mom wishing her daughter to succeed in the world. From the mom see herself in her and telling her life lessons and overcome hardships. If you really think about it, Lee Ann was singing about Aubrie and she knew she’ll follow into her footsteps and have a career in country music. You kind of say, Aubrie lived out Lee Ann’s wish of mother seeing her daughter successful. It’s that little detail that took I Hope You Dance to a another level for me. Lee Ann has had a great career and I glad she getting the proper recognition she truly deserves.

  2. not a fan – i liked her funny song, “I’ll Think of a Reason Later (Tony Martin & Tim Nichols). (Funny songs seem to get hardly any respect from critics or have any chart success). I wasn’t impressed by “I Hope You Dance”. If I had to pick a favorite it would be “I May Hate Myself in the Morning”.

  3. Tremendous talent. My favorite is There’s More Where That Came From

    Favorite singles:
    Last Call
    Something Worth Leaving Behind
    I Hope You Dance
    I May Hate Myself In The Morning
    Twenty Years and Two Husbands Ago
    Ashes By Now

  4. Of all the rankings on this list, I’d say this one baffles me the most. With only one, #1 country hit and barely seven top-10 country singles to her credit, I don’t really “get” how Lee Ann Womack comes out ahead of Tanya Tucker, Barbara Mandrell, Miranda Lambert, Carrie Underwood, Crystal Gayle, and Lynn Anderson, chiefly among other acclaimed, prolific hitmakers in your top 40. Nevertheless, I do agree that Lee Ann Womack is one of the better, more-interesting country artists to come along in the past 20 years or so, and I’m sure her fans on this site will be delighted with your high assessment.

  5. Love her, but not clear how Lee Ann made a 17 spot jump on the list ahead of some true blue legends from her output over the last 10 years. She only put out two albums in that time period and I wouldn’t call either of them her peak.

  6. After this ran, I started slowly working my way through Lee Ann’s catalog in an effort to familiarize myself with her work beyond “I Hope You Dance”. So far, I’ve gone into two cuts – “All the Trouble” and “I’ll Think of a Reason Later”. Like both of ’em. Maybe her entire self-titled album should be next in my journey through the Womack catalog, as my dad has a copy.

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