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The Best Lee Ann Womack Songs That Set The Standard For Country Female Vocalists In The ’90s

Lee Ann Womack Songs

After working in the music industry as a promoter and songwriter for a number of years, Lee Ann Womack became a breakout contemporary artist herself with the release of her eponymous debut album in 1997. Lee Ann Womack songs about love gone wrong or attraction that lingers long hit the hearts of many country fans.

In honor of Lee Ann Womack‘s milestone, let’s take a look back at some of her greatest hits so far.

1. I Hope You Dance

From: I Hope You Dance (2000)

This iconic song – about taking chances and not being afraid to try something new – only grows even stronger and more important with time. Upon its release, it became an almost instant No. 1 hit on Billboard’s Hot Country Songs chart and was a giant crossover hit, peaking at No. 14 on Billboard Hot 100. 

Of course, “I Hope You Dance” seemingly received an endless number of awards and recognition, including Best Country Song from the Grammy Awards. It’s absolutely one of the biggest selling songs in the genre’s history, putting Womack’s star on the rise.

2. A Little Past Little Rock

From: Some Things I Know (1998)

Womack released another solid country single that’s laced with fiddle and sensuous lead guitar work that perfectly complements her emotion-laden vocal performance. The poignant ballad tells the narrative of a woman driving down the highway. While she doesn’t have an exact destination in mind, she’s satisfied that she’s headed away from her troubled relationship.

3. I May Hate Myself in the Morning

From: There’s More Where That Came From (2005)

“This is the kind of stuff I grew up listening to,” Womack said about the song. Backed by acoustic guitar, with steel guitar and string fills, “I May Hate Myself in The Morning” is a ballad that tells the story of a woman who’s fully aware of the consequences of spending a passionate night with a man who’s no longer into her, yet she did it anyway.

4. Solitary Thinkin’

From: Call Me Crazy (2008)

Womack does what she does best in “Solitary Thinkin'” – and that’s drowning her sorrows with a few glasses of the hard stuff as she spends the entire night in a bar. After all, she would rather have lonesome drinking than just give up. 

This slow-burning piece is written by country singer-songwriter, and actor Waylon Payne at a Los Angeles bar, which he later found out was actually a prostitute bar.

5. Last Call

From: Call Me Crazy (2008)

Written by Erin Enderlin and Shane McAnally, this haunting lament is filled with hints of rage and disappointment by Womack. Tired of being her man’s “last call” whenever he spends a wasted night in a bar, she is now refusing to answer him and chooses to move on.

The song was well received by critics and earned a nomination for Grammy Awards for Best Female Country Vocal Performance.

6. Ashes by Now

From: I Hope You Dance (2000)

Written and recorded by Rodney Crowell in 1980, “Ashes by Now” has since been cut several times by various musical artists. It was notably covered by Womack in 2000, with her version becoming the most commercially successful.

The song is a narrative of someone who’s holding onto a love that’s causing more harm than good for them.

7. (Now You See Me) Now You Don’t

From: Some Things I Know (1998)

Released from her gold-certifying second album, this brief, sassy little number is about a woman on her way out of a sour relationship. The song’s poignant lyrics beautiful blend with its lively melody and remarkable guitar work. Meanwhile, Womack’s voice has perfectly conveyed the emotion of a desperate, spurned woman.

8. I’ll Think of a Reason Later

From: Some Things I Know (1998)

Womack continued to showcase how fierce she is. In this song, she sings her disdain as she discovers that her ex-lover is about to marry some girl from Denver. While the new girl may be the best one out there – she may be an angel who brings the homeless blankets and dinner, or perhaps she’s a regular Nobel Peace winner – Womack still has no reason to like her.

9. The Way I’m Livin’

From: The Way I’m Livin’ (2014)

While it was not as commercially successful as her other songs, “The Way I’m Livin’ earned positive reviews from critics. It finds Womack lamenting about a woman who wants to change her ways and do something different but is struggling with how she’s going to be able to. “I guess this song is just at a point where a person’s sort of hit bottom,” the singer said about the song, adding that it hit her the first time she heard it.

10. Why They Call It Falling

From: I Hope You Dance (2000)

Written by Don Schlitz and Roxie Dean, this stunning ballad puts Womack’s twangy vocals on full display as she sings about how love moves in mysterious ways. It made her wonder why it’s even called falling in love when she couldn’t get her feet to touch the ground whenever they were together. And when they talked about forever, she’s pretty sure she’s soared to heaven for some time.

More Lee Ann Womack Songs, From Honky-Tonk Heartbreakers To Soaring Ballads

It’s truly fascinating how Lee Ann Womack sings like she has lived each and every lyric. So, we’re adding up more of her songs that took our breath away.

  • Does My Ring Burn Your Finger
  • The Fool
  • You’ve Got to Talk to Me
  • Something Worth Leaving Behind
  • He Oughta Know That by Now
  • Never Again, Again
  • The Wrong Girl
  • Buckaroo
  • Twenty Years and Two Husbands Ago
  • There Is a God
  • Forever Everyday
  • Finding My Way Back Home
  • Don’t Tell Me
  • Send It On Down
  • Chances Are

So, which among these Lee Ann Womack songs are your favorites?

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