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The 10 Best Lee Ann Womack Songs, Ranked

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Not many country music artists have mastered the ability to release both traditional country-leaning singles and pop-crossover hits while keeping their original artistry intact, but Lee Ann Womack is certainly one of those artists. Throughout her 20-year career, which saw its peak late '90s and early 2000s, Womack has always succeeded in flawlessly melding the traditional country sound while keeping up with current trends. The Jacksonville, Texas native, who is wife producer Frank Liddell and mother to Aubrie Sellers, has released nine studio albums, 30 singles and has been nominated for and won multiple Grammy, ACM, CMT and CMA Awards. With such a robust and successful discography of country songs, it's hard to choose just a few tunes from Womack that make the cut, but here are the 10 best Lee Ann Womack songs, according to Wide Open Country.

10. "Does My Ring Burn Your Finger" 

In this fiery song from her 2000 album, I Hope You Dance, Lee Ann Womack unabashedly confronts a husband in a marriage gone wrong. Clearly brokenhearted, but also maintaining a sense of pride, Womack asks, "Does my ring burn your finger? Did my love weigh you down? Was the promise too much to keep around?" The song's lyrics and Womack's classic voice are paired with equally defiant country instrumentals. The tune, written by Nashville songwriting couple Julie Miller and Buddy Miller, landed at No. 23 on the charts.

9. "The Fool"

Womack's "The Fool" brings fans back to the singer's self-titled, debut album released in 1997. In this piano-laden tune peppered with fiddle and steel guitar, Womack sings of a love triangle, in which she's in love with a man who is in love with someone else. Throughout the song, she sings to the objects of her man's attention, singing "I'm the fool in love with the fool who's still in love with you." As her second single, "The Fool" was Womack's first song to break the Top 20, landing at No. 2 on the Billboard country chart.

8.  "Never Again, Again" 

Womack's Texas roots especially come through on her debut single "Never Again, Again." In this tune that swayed traditional country even in 1997, Womack sings of her resolve to officially leave a past relationship in the past, which doesn't always work out for her. The song was a solid showing for a debut single, landing at No. 23. With its country phrasing, steel guitar and fiddle, the song served to establish Womack as an artist who makes the kind of music that would pique the interest of any country traditionalist.

7. "I'll Think of a Reason Later" 

Womack saw success with her debut album and followed it up with her sophomore effort, Some Things I Know, which produced four singles. One of these was the humorous "I'll Think of a Reason Later," in which Womack decides she doesn't like her ex-boyfriend's new fiancé, but she doesn't have a particularly good reason -- other than jealousy. "I really hate her. I'll think of a reason later," sings Womack. This upbeat tune landed just shy of the No. 1 spot on the country chart, giving Womack her fourth No. 2 single.

6. "Ashes By Now" 

Womack confronts heartbreak yet again in "Ashes By Now," from her I Hope You Dance album. Albeit upbeat, the song is directed at a cheating partner with Womack singing, "For as much as you burn me, baby, I should be ashes by now." The song was written by Rodney Crowell and originally released by him in 1980. Emmylou Harris also recorded the song for her 1981 album, Evangeline, before Womack released her version in 2000.

Read More: Chris Stapleton Covers Lee Ann Womack's 'I Hope You Dance' For St. Jude Fundraiser

5.  "I May Hate Myself In The Morning" 

Womack's career took off at an unstoppable pace in 2000 (we'll get to why later), and she kept the hits coming into the mid-to-late 2000s. In 2004, Womack released "I May Hate Myself In The Morning," a traditional-leaning tune which finds Womack falling back into an old relationship. The artist sings about how she and her ex-love continue to "wind up in each other's arms," proclaiming that even though she may hate herself in the morning, she's going to love him tonight.

4. "He Oughta Know That By Now"

Another mid-2000s gem from Womack comes in the form of 2005's "He Oughta Know That By Now" from There's More Where That Came From. In this single, released after "I May Hate Myself In The Morning," Womack laments her relationship with an absent partner, singing that he "oughta know" what she needs from their partnership by now. Womack calls it like she sees it in the chorus singing, "It's just too hard to hold onto what is never around / He oughta know that by now." In a powerful turn of events at the end of the song, Womack leaves her husband and her wedding ring in the dust.

3. "A Little Past Little Rock"

Lee Ann Womack has displayed her mastery of heartbreak songs throughout her career, and this can be seen in her 1998 single, "A Little Past Little Rock." This nostalgic, freewheeling tune finds Womack on the open road, driving away from heartbreak in Dallas. The song uses the road trip as a sort of metaphor for her broken heart, which is a tool that has been utilized in many songs since. In the song, she notes that she's physically "a little past little rock," but mentally, she's "a long way from over" her love. The song, which features backup vocals from her ex-husband and songwriter Jason Sellers, landed at No. 2.

2. "Last Call"

Lee Ann Womack sings about the temptations of falling back into an old relationship yet again in 2008's "Last Call." However, unlike "I May Hate Myself In The Morning," Womack ignores the late night calls from an ex-love in "Last Call", as she knows he'll never change. Womack paints a picture of the man in the song who only calls her when he's at a bar at closing time and needs a ride home. While Womack is confident in her decision to protect her heart, the hurt in her voice is clear. "Last Call," from her Call Me Crazy album, landed at No. 14.

1. "I Hope You Dance" 

While some could debate where each of these songs belong on the list, no one can argue that Womack's top song is 2000's "I Hope You Dance." This song, which served as the title track of the album, finds Womack encouraging listeners to stay positive and make the most out of life. Womack uses various visuals to get this message across, such as "I hope you never fear those mountains in the distance / Never settle for the path of least resistance," but most importantly, "I hope you dance." The song became an international crossover hit, landing at No. 1 on all the country charts, as well as charting on the all-genre and pop charts, among others. The song took home a CMA Award, ACM Award, Grammy Award, and other accolades, and continues to be an impactful song in country music to this day.

Honorable mentions: "(Now You See Me) Now You Don't," "Why They Call It Falling," "Something Worth Leaving Behind," "The Wrong Girl," "Solitary Thinkin,'" "Mendocino County Line" (duet with Willie Nelson), and "The Way I'm Livin'.'

This story originally ran on May 29, 2021.

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The 10 Best Lee Ann Womack Songs, Ranked