Lee Ann Womack's 10 Best Songs: Critic's Picks

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Lee Ann Womack poses at The Life & Songs of Kris Kristofferson produced by Blackbird Presents at Bridgestone Arena on March 16, 2016 in Nashville, Tenn.

Subtle would never be a word that one would use to describe the career of Lee Ann Womack. The Jacksonville, Texas native aimed for – and hit the hearts of Country Music fans dead center in 1997 with the release of “Never Again, Again,” a song that evoked comparisons to legends such as Loretta Lynn and Dolly Parton. And, as impossible as it is to believe, she has only gotten better with time.

Whether singing heartbreaking ballads about love gone wrong, or smoldering three-minute epics about the attraction that lingers long after conventional wisdom would have you believe it should have died, there’s an honesty when Lee Ann Womack sings. You can hear it in her emotional delivery when she talks about making a decision that she knows is wrong, but can’t help herself. And, though she has been married to producer Frank Liddell for close to two decades, she makes you believe she has lived each and every lyric. It’s hard to imagine anyone else in today’s marketplace recording these types of songs, let alone to do them as good. Look for that trend to continue when she releases her highly anticipated ninth studio album, The Lonely, The Lonesome, and The Gone on Oct. 27. Here are ten Lee Ann Womack song moments that left us all with our jaws dropped in disbelief!

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10. Lee Ann Womack - "Twenty Years and Two Husbands Ago"

Womack paired with legendary tunesmith Dean Dillon and Dale Dodson to pen this ballad about a woman looking back at her life through an honest pair of glasses. From the classic 2005 There’s More Where That Came From album, this sounded very similar to the classics that Billy Sherrill was cutting on Tammy Wynette in the 1970s. Few other female vocalists would even attempt a song in this brutally frank manner, but Lee Ann Womack sounded like she had been there, note for note.

9. Lee Ann Womack - "The Way I’m Livin'" 

The lead single from her 2014 Sugar Hill disc, this song was about as real as one could get. The song served as a warning to others to not follow her lead or her example, as she knew the difference between right and wrong -- but couldn’t resist walking the other side of the path. In a lot of ways, this song is very much reminiscent of some of the Gospel work of the Louvin Brothers. It’s in no way a song you’ll hear in Church, but it speaks about the tight line between wrong and right, and this Lee Ann Womack song was definitely one of her brighter moments on record.

8. Lee Ann Womack - "Last Call"

Shane McAnally and Erin Enderlin partnered up for this 2008 recording that was all about the times when the phone rings late at night -- and the reasons for it. In the lyrics, Womack offers an anguished take as the woman who doesn’t want to be the final resort of the night, one who is longing for something more than just a reach out of desperation at closing time.

7. Lee Ann Womack - "The Fool"

Womack wasn’t too sure when she was pitched this song for her debut album. According to an interview for Billboard at the time, she said she thought it was good, but not in the same league with "Never Again, Again," the song that launched her career one single prior. However, the fans felt differently, making this simple yet complex song of heartbreak her very first top ten single -- one that just narrowly missed the top spot in the fall of 1997.

6. Lee Ann Womack - "I’ll Think Of A Reason Later"

There’s not a tremendous amount of tempo in the Lee Ann Womack song catalog, which made this 1999 release stand out a bit on Country Radio. The songstress handled the lyrics -- about seeing the excitement that people in town were feeling over the nuptials to her ex and his new lover -- with the right combination of anger, humor, and -- just a little bit of snark!

5. Lee Ann Womack - "Does My Ring Burn Your Finger"

Husband and wife Buddy and Julie Miller submitted this fiery number for I Hope You Dance in 2000. While the title track captured the hearts and imagination of fans all over the world, this recording is worth seeking out. It was a bare bones traditional arrangement, where Womack delivered what just might be her most dominant vocal performance – so far. Do us a favor. Check out her performance of this song from the 2001 CMA Awards on YouTube. We get paid to write words describing such moments, but damn. Sometimes, there are none that can aptly describe it.

4. Lee Ann Womack - "I Hope You Dance" 

Mark Sanders and Tia Sillers’ lyrics were very much open-ended – meaning the song could be taken to reference many different people when it came to the identity of "You." In the heartfelt video, the singer performed the song to her daughters, but whether it be children, a lover, or a good friend, this song helped to put Womack’s star on the rise upon its’ release in 2000.

3. Lee Ann Womack - "A Little Past Little Rock"

There has always been somewhat of a retro vibe to the music of Lee Ann Womack. Of course, much of her later work includes that feel, but even as early as her 1998 sophomore album Some Things I Know, you could tell that she was an old soul -- when it came to the sounds that influenced her. Producer Mark Wright set Womack’s vocal front and center with a string performance that would have made Owen Bradley and Patsy Cline applaud with approval. And, when it comes to attempting to escape a heartache, this Lee Ann Womack song worked whether you were leaving Little Rock, Atlanta, or Las Vegas.

2. Lee Ann Womack - "Never Again, Again"

When radio programmers heard her 1997 debut single, some applauded loudly -- while others balked. "This is too Country," many would say during the heyday of artists such as Shania Twain. That partly explains the No. 23 peak of this song on the singles charts. But, rankings don’t tell the whole story -- all of the time. The stations that did play this received phenomenal response, helping the album to go Gold on the strength of this song alone. The song was an unlikely one to hit, but from the first notes out of Lee Ann Womack’s mouth, you knew this was the beginning of something special. And, indeed it was.

HONORABLE MENTION. Lee Ann Womack - "When You Gonna Run To Me"

As much as Womack has been praised for her traditional Country stylings, she can also wring emotion out of more crossover-flavored material. This cut from her 2002 Something Worth Leaving Behind disc never got the attention it deserved, but this was -- and still is -- the keeper of the disc. With a dreamy arrangement, the singer grabbed a hold of the yearning-filled lyrics, giving arguably the most seductive performance of her career.

1. Lee Ann Womack - "I May Hate Myself In The Morning"

Sometimes when you first hear a record, you might think 'This song could have used a little bit of this or that.' Nobody said those words when Womack released this one in late 2004. The lyrics -- about a relationship that was very much on again, off again -- seemed like they could have been taken from a 1982 episode of Dallas,with their gripping sense of frankness. In the song, Womack gave an impassioned performance about a woman who knew she shouldn’t give into the temptation of periodically returning to the source of her greatest flame -- yet she knew the spark was too strong to resist. A dozen years later, this one still ranks as one of the best moments for a female vocalist in the history of Nashville -- or for that matter, any gender!


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