Not many country music stars from the past 30 years or so have mastered the ability to release both traditional-leaning singles and pop-crossover hits while keeping their original artistry intact, with Lee Ann Womack certainly making that list. Throughout her 20-year career, which saw its peak in the late '90s and early 2000s, Womack has joined Reba McEntire, Brooks & Dunn and other peers in flawlessly upholding a traditional country sound without losing sight of current trends.
The Jacksonville, Texas native, who is the of wife producer Frank Liddell and mother of fellow country artist Aubrie Sellers, has released nine studio albums (the most recent being 2017's The Lonely, The Lonesome & The Gone) and 30 singles en rote to multiple Grammy, ACM, CMT and CMA Award nominations and wins.
With such a robust and successful catalog of country songs, it's hard to choose just a few tunes from Womack that make the cut, but here are her 12 best, according to Wide Open Country.
12. "Good News, Bad News" (with George Strait)
On King George's 2005 album Somewhere Down in Texas you'll find a gorgeous, acoustic-driven duet by two of the leading old-school country voices to hail from the Lone Star State. It's not an obvious pick, but you'd be hard-pressed to find a more emotive vocal performance by Womack.
11. "20 Years and Two Husbands Ago"
This Womack, Dean Dillon and Dale Dodson co-write from 2005's There's More Where That Came From trumps other potential picks here because it best spotlights its performer's undeniable skill as a countrified storyteller and top-flight vocalist.
10. "Does My Ring Burn Your Finger"
This fiery song from Womack's 2000 album I Hope You Dance unabashedly confronts a husband in a marriage gone wrong.
The song's lyrics and Womack's classic voice are paired with equally timeless country instrumentation. The tune, written by Nashville songwriting couple Julie Miller and Buddy Miller, landed at No. 23 on the charts.
9. "The Fool"
In this piano-laden tune peppered with fiddle and steel guitar, Womack sings of a love triangle, in which her character's heart belongs to a man who has fallen for someone else. Throughout the song, she sings to the object of the man's attention: I'm the fool in love with the fool who's still in love with you."
As her second single from her self-titled debut album (1997_, "The Fool" was Womack's first song to break the Top 20, landing at No. 2 on the Billboard Hot Country Songs chart.
8. "Never Again, Again"
Womack's Texas roots especially come through on debut single "Never Again, Again." This tune that strayed traditional (even by 1997 standards) captures a woman's resolve to officially leave a relationship in the past, which doesn't always work out for her.
With its country phrasing, steel guitar and fiddle, the song established Womack as an artist who makes the kind of music that would pique the interest of even the pickiest traditionalist.
7. "I'll Think of a Reason Later"
Womack followed her initial success with sophomore effort Some Things I Know, which produced four singles. One of those was the humorous "I'll Think of a Reason Later," which is about a woman who doesn't like her ex-boyfriend's new fiancé. She doesn't have a particularly good reason-- other than jealousy.
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 with "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.
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 once again finds her falling back into old habits.
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, Womack laments a relationship with an absent partner, singing that he "oughta know" a woman's needs by now. Womack calls it like she sees it in the chorus: "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, the husband gets left behind while her wedding ring sits in the dust.
3. "A Little Past Little Rock"
Womack has displayed a mastery of heartbreak songs throughout her career: a claim backed up by her 1998 single "A Little Past Little Rock."
This nostalgic, freewheeling tune places Womack on the open road, driving away from heartbreak in Dallas. It uses the road trip as a metaphor for a broken heart. Its lyrics tell of someone who's physically "a little past little rock," but mentally, she's "a long way from over" her love.
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," late night calls from an ex-love get ignored in this Shane McAnally and Erin Enderlin co-write.
The song paints a vivid picture of a man who only calls the lead character when he's at a bar at closing time and needs a ride home. While the narrator 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 many will debate where or if the above selections belong on this list, few should argue that Womack's top song is 2000's Grammy Award-winner, "I Hope You Dance."
This song finds Womack encouraging listeners to stay positive and make the most out of life. She 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."
It became an international crossover hit, landing at No. 1 on all the country charts, as well as cracking the all-genre pop chart, among others.
Honorable mentions: "You've Got to Talk to Me," "Mama Lost Her Smile," "(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'"
READ MORE: The 10 Best Chris Stapleton Songs, Ranked
This story originally ran on May 29, 2021.
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