Fifteen Favorites: The Lee Ann Womack Edition

For several reasons I’ve been feeling nostalgic lately. I’ve been revisiting several artists that impacted my childhood and my early love for country music. They may not necessarily be all-time favorites today, but for several reasons I gravitated toward them, their sound, and country music in general … and got this crazy journey started. The 2000s aren’t usually seen as a notable decade for the genre, and indeed, I know several online friends who stopped listening to country radio altogether by the end of the decade and just stopped listening to country in general before they found it again years later. So it’s ironic that, as a kid who grew up in the 2000s, this is the decade I consider to hold the greatest influence for me.

So while this isn’t the most original idea in the blogosphere, I’d like to start a new series – one in which I take deep-dives of those artists and explore 15 of their songs I consider to be my favorites. The goal with this isn’t revolutionary; I just want something loose, random, and fun, and I want to invite y’all in on it, too. In fact, some of these are already scheduled to be collaborative posts with other writers. Of course, you, the readers, are always welcome to request artists for this particular series, so long as I can find 15 songs of theirs I like. While this will initially be used to explore artists that impacted my childhood, it will eventually expand into modern day favorites. And I’m always happy to detour along the way, should a request surface. Why 15 songs? Simply put, anything less than 10 is lacking and anything more than 20 is overdoing it. I even had a hard time thinking of 25 songs I really loved from my all-time favorite artists.

So, that’s that. My first artist to be explored with this series will be Lee Ann Womack. From there, who knows? Enjoy, and feel free to share your own favorites as we move along.

Anyway, as a child of the 2000s, it makes sense why I gravitated toward Lee Ann Womack. It’s just the timing that was off for me. I mean, of course my mother dedicated “I Hope You Dance” to me on several occasions; duh. But you see, I didn’t start listening until around 2007, and Womack notched her final top 20 hit in 2008. But, wow, am I ever thankful for “Last Call.” I loved it. It’s going to sound cliché, especially from the perspective of a then-10-year-old who couldn’t relate to a lick of the song’s messages of cheating and drinking, but I loved the bitterness and pain she expressed. It’s what made the music “real,” for me (whatever that means), not its sound. She wasn’t the most prolific writer, but I’ve never bought into the idea that penning one’s own material automatically leads to better music anyway. Performance and presentation matters just as much, folks, and Womack has always understood that.

I guess what I’m saying is, despite only sinking my teeth into Womack’s material near the end of her mainstream radio career, she impacted my early love for the genre and helped me understand its universal appeal better than most artists during this time period. She deserved so much better at country radio, and if you’re curious as to what halted her success, Kyle’s Korner has a fantastic deep-dive on the subject. Still, while she doesn’t have the biggest discography, song-for-song I’ve always admired her consistency, and I wished we had heard more from her in the last decade. At the very least, she’s one of countless artists who’s found success outside of country radio and has continued to follow her artistic muse for the better. For now, though, let’s rewind the clock and examine 15 of my favorite songs from her. Feel free to share yours, too.

No. 15, “Don’t Listen to the Wind” (written by Julie Miller)

Ironically enough, while The Way I’m Livin is right up there with There’s More Where That Came From as my favorite Lee Ann Womack album, it’s always a project I consider strongest taken as a whole. And yet it’s probably the album we’ll explore the most here – Womack’s artistic comeback record that found her expanding her sonic palette for the better. This isn’t the best cut she’s recorded by Julie (or Buddy) Miller, but it’s damn close – a Gothic-tinged, grizzly song about being haunted by an old lover’s memory. It’s a song where the subtext and presentation do the heavy lifting, where the darker electric stabs and ragged fiddle edges ramp up excellently against the percussion to echo this haunting pushing the point of insanity for our character. And while Womack nails the frustrated desperation, it’s the sort of haunting I’ve always found alluring enough to return to time and time again. Sidenote: A bluegrass album from her would kill.

No. 14, “A Little Past Little Rock” (written by Brett Jones, Jess Brown, and Tony Lane)

Answering what Womack’s biggest single is is a no-brainer. Spoiler alert: we’ll get to it. But trying to find an objective best cut from her? Well, that’s tricky. Her discography is so consistently excellent that I haven’t seen anyone list the same top favorite twice, and I’m sure that will be true of my own eventual top pick. But if there’s one that pops up time and time again in those discussions, it’s this single – another song about trying to outrun an old flame. Only, this one is far more hopeful, and, between the burnished touches of warmer bass and harmonic creeping in on the low-end for the hook, a lot more soothing, too. It’s not so much escapism as it is making a clean break to find some clarity, because sometimes that’s the first step to actually finding an escape.

No. 13, “The Lonely, the Lonesome, and the Gone” (written by Adam Wright and Jay Knowles)

Of course, sometimes that escape comes in a blacked-out haze and without a happy ending. And if that sounds like a familiar theme, it’s because the title track from Womack’s 2017 album decides to play to country music clichés by cutting to the heart of the matter – that despite the lavishly upbeat situations fools find themselves in as they leave their heartaches behind, the resonance always comes through in the pain, nothing less. And with an atmospheric haze that’s just as somber as its subject, it’s another example of how Womack understands country music’s true heartbeat.

No. 12, “The Way I’m Livin’” (written by Adam Wright)

On the other hand, there’s nothing wrong with embellishing the details a little or adding some stomp into the mix. Womack came roaring back in a big way with her righteously awesome comeback single in 2014, where the thunderous percussion builds around a sordid tale of temptation and succumbing to one’s own vices, which she enjoys. If there’s a real standout here, it’s Womack herself, who revels in her metaphorical trip to meet the Devil in a way that can feel simultaneously seething … and kind of fun. Post-Call Me Crazy, Womack could have tried to fit in with current trends, but instead, she followed her own path. And considering the former is a path of darkness all on its own, I’m glad she chose this one instead.

No. 11, “Never Again, Again” (written by Barbie Isham and Monty Holmes)

… I sure do like Womack’s songs of temptation, don’t I? The first time was the definite charm here, a song delivered with a deadpan hook that, sure, is a bit more straightforward than other entries here, but hits with more punch when delivered through the harder-hitting sonic palette. Yes, it’s a fairly familiar traditional structure that I’m bound to like before lyrics even come into play, but as I’ve noted before, it always comes down to the emotive presentation. In this case, Womack’s heartache has rarely sound better.

No. 10, “Mendocino County Line” (written by Bernie Taupin and Matt Serletic)

When you consider the concept and individual artistic styles, this duet pairing really makes no sense on paper. I love it anyway and didn’t want to forget it here. The execution proves otherwise anyway, especially when Nelson’s tender, restrained performance balances well against Womack’s epic, soaring take that shows how differently both partners look back on their relationship and yet still come to the same general conclusion that it’s something worth missing. The buildup in performance certainly favors Womack, especially with the huge swell of strings that gives this fling one last golden hurrah.

No. 9, “Stubborn (Psalm 151)” (written by Don Schlitz and Brett James)

You know, I’m actually surprised there aren’t more cuts from There’s More Where That Came From on here. Seriously, it’s damn-near a modern masterpiece of a collection, and this is one of its best moments. Familiar to Womack’s themes of desperation and longing to rise above one’s own vices, “Stubborn” addresses that conflict head-on, tackling her resistance between her faith in a higher power and a few familiar demons named stubbornness and pride. And the thing is, there’s no easy answer at the end here – just a realization that the vicious cycle is one she doesn’t endure or obsess over alone. Having the courage to walk on anyway is a victory in and of itself. Complex while still being universal in its overall appeal, it’s a deep cut that can’t be overlooked.  

No. 8, “I Hope You Dance” (written by Mark D. Sanders and Tia Sillers)

Only in circles like these – where, let’s face it, we’re all music snobs – do I have to justify having the big hit single here, let alone this high. Yet out of all the cheesy ballads that invaded country radio around this time period, this is the one I unabashedly love. Maybe it’s because it doesn’t feel like a cheesy, platitude-filled ballad. Tone has always mattered to me, and between the swell of darker strings and Womack’s serious delivery that works for a mother hopeful yet scared for her child’s path on the  journey of life, it’s a song that can acknowledge and work with deeper stakes. It’s “I Hope You Dance,” not “You Will Definitely Dance.” It’s a song that remembers to emphasize humility and empathy and encourages the confidence needed to chase after a dream. Given how Aubrie Sellers is now forging her own path, I’d say everything worked out just fine.

No. 7, “Does My Ring Burn Your Finger” (written by Buddy Miller and Julie Miller)

There’s nothing like going from the big, epic single to another brutally dark cut from the Millers. I think most people even forget these two singles came from the same album. Even I’m surprised this creepily cheery, Gothic, bluegrass-inspired number made it as a single at country radio, because considering where that entity was heading at the time, this was a real breath of fresh air. And for as haunted as our character feels by her dearly departed lover’s departure, one has to wonder if her questions asked suggest that he really left her or if she was driven to commit a crime that shall not be named and is now haunted by its aftermath. It’s awesome either way, but I’m kind of rooting for the latter. In hindsight, material like this is probably what torpedoed her mainstream momentum more than Something Worth Leaving Behind, but we, the fans, still reap the benefits to this day.

No. 6, “Mama Lost Her Smile” (written by Adam Wright, Lee Ann Womack, and Waylon Payne)

This has the sort of cut-throat intimacy that reminds me of a Gretchen Peters song, and from me, that’s damn-near the highest praise I can offer. The Lonely, the Lonesome, and the Gone is far from my favorite Womack album, but it is likely her darkest without being overly showy about it. If the title track was looking to cut through familiar country music clichés, this is more about cutting to the truth of what caused a broken family to finally fracture. It’s another song that purposefully leaves more questions than answers, like whether this family’s move away from what they once called home was the instigator behind the fall or if it was just another wheel in motion for an unhappy couple. The pictures won’t tell her, because they only depict the good memories, which in a way helps ease the pain from the older perspective through which this is told. But it still leaves those darned questions.

No. 5, “Last Call” (written by Shane McAnally and Erin Enderlin)

There’s two songs in my top five that play around with their titles to ultimately depict the end of a relationship, and I don’t even really want to call this the lesser of the two when we’re this high up the list. It’s certainly the more bitter though, where Womack’s frustrations with her flighty, alcoholic significant other come to blows in a way that suggests it’s been a long time coming. And while it is somewhat tough saying goodbye – that second verse in particular is gutting in justifying her response – it’s more like cutting a cord that needed to be severed a long time ago. For as much as she’s always been praised as a traditionalist, what I’ve always admired more is her ability to blend the old with the new in a way that’s fresh and keeps country music’s messages ringing onward. “Last Call” may have been the last single that the general public really knew about, but it really shouldn’t have been her own last call – just sayin’.

No. 4, “Send It On Down” (written by Chris Knight and David Leone)

For as much as I’ve favored songs here for their technical presentation, sometimes all it takes for Womack to shine is, well, herself. Indeed, against the stark echo of acoustics and pedal steel comes a desperate cry for help from a character aware of her alcoholism and its roots who just needs the chance to overcome it. And while she turns to the God paradigm for help, the striking part is, she knows she’s doing everything she can to turn against it. She hears the “good folks” sing at church while she sits in the bleachers at the football field looking for an escape, with the subtext suggesting she’s about to lean into the kind of permanent one that would traditionally turn her against that higher figure anyway. It makes the cry for help that much more harrowing and urgent, and it’s arguably one of Womack’s finest moments on record.

No. 3, “He Oughta Know That By Now” (written by Clint Ingersoll and Jeremy Spillman)

It’s hard to know what to say when a lot of the reasons for why I love this were outlined in my “Last Call” blurb. What’s always won out for me is the greater establishment of context, where the title hook takes on a new form every time and somehow gets more and more brutal, at that. And the sad part is, there’s really no one at fault or to blame, necessarily. He’s tethered to his job and she’s in need of companionship that he can’t provide. It’s simply a case of things not working out, even despite all of those subtle messages and implications from her to him that go ignored. You know how it ends, but it doesn’t make that final verse any less effective. Couple that all with a bouncy acoustic melody I just adore that softens the final blow well, and you have another single that should have led to so much more.

No. 2, “Ashes By Now” (written by Rodney Crowell)

Well, it’s certainly brighter than the Rodney Crowell version, and I can’t fault those who prefer the original that includes another verse cut here. I can’t even say I really expected this song to land this high for me, and then I revisited it and had that sharp instrumental hook lodged into my brain for days. Womack’s bitterness tends to frame itself much more seriously, but I’ve always loved her performance here painted with a dramatic flair that’s just more urgent than anything else in her discography. Couple that with a strong groove (and those bongos!) and an equally strong finish from the backing vocalists that adds potency and fire to that hook, and we have one of Womack’s most underrated songs. Heck, it was almost my favorite from her, but there’s still one more to get to.

And before I unveil my No. 1 pick, let’s run through some honorable mentions, starting with …

“The Fool” (written by Charles Stefl, Eugene Ellsworth, and Maria Cannon – Goodman)

“There’s More Where That Came From” (written by Chris DuBois and Chris Stapleton)

“Tomorrow Night in Baltimore” (written by K. Price)

“Twenty Years and Two Husbands Ago” (written by Dale Dodson, Dean Dillon, and Lee Ann Womack)

“I Know Why The River Runs” (written by Julie Miller)

“When You Get to Me” (written by Bill Luther and Marv Green)

“The Wrong Girl” (written by Liz Rose and Pat McLaughlin)

“After I Fall” (written by Bill Kenner, Mark Wright, and Ronnie Rogers)

And now, my final entry:

No. 1, “I Think I Know” (written by Mark Nesler, Tom Shapiro, and Tony Martin)

This song floors me every time I listen to it, and when it comes to deciding a favorite Womack single, nothing else really comes close for me. What’s frustrated me more over the years is how misunderstood it’s been, the sort of song that builds its premise by name-dropping fallen country legends but speaks to so much more than just establishing useless credibility. I’ve noted numerous times before that despite being a performer first and foremost, Womack understands country music that cuts to the heart of the matter, and she knows how to emote it. So when she references Keith Whitley, Hank Williams, and Johnny Cash and how their deaths are linked by demons and a pain she understands just as well, she does it again. We don’t listen to glorify these acts or try and mimic their paths. We do it because we understand how there was a sad desperation evident in all of them to overcome their temptations and desperation, and that they didn’t is why their stories – their warnings – live on. If we’re being honest, we don’t directly relate to a lot of music out there. We’re lucky if we do at all. But beyond the clichés and plot devices, we relate to country music because we empathize and understand where those feelings stem from, and root for the happy ending even despite knowing it will never come. It’s why I love their music, it’s why I love Womack’s music, and it’s why I can’t think of a better song to summarize why.

8 thoughts on “Fifteen Favorites: The Lee Ann Womack Edition

  1. I havent heard all of those as I never really dig I to her career outside of the most famous hits. I did come across an excellent cover of Bob Dylan’s Gotta Serve Someone on the Muscle Shoals tribute project. It features Willie Nelson, Jamey Johnson, Chris Stapleton and Lee Ann Womack on it and it’s an incredible piece of music. It actually got me interested in going make into her discography. Never got around to it but this article certainly gives me the road map to do so.

    Liked by 1 person

  2. First off, I love this idea for a feature and I’m looking forward to the other artists that you’ll be featuring.

    Back when I owned CDs, I owned (and loved!) Lee Ann Womack’s first three album, so my list will be heavily biased towards those albums. I am only familiar with certain songs from her other albums, but here is my list.

    1. Don’t Tell Me (this is easily #1 for me – simply a beautiful song, exquisitely sung and produced).
    2. The Fool
    3. Send it on Down
    4. Some Things I Know
    5. A Little Past Little Rock
    6. I’ll Think of a Reason Later
    7. Never Again, Again
    8. Make Memories with Me
    9. I May Hate Myself in the Morning
    10. Buckaroo
    11. Why They Call it Falling
    12. Trouble’s Here
    13. Twenty Years and Two Husbands Ago
    14. The Bees
    15. I Think I Know

    Liked by 1 person

    1. Thanks, Frank! Only have done a few others thus far – Eric Church and James McMurtry – but I’m hoping to one on Sunny Sweeney sometime very soon!

      Great list, btw. I keep it at 15 just to keep things even-keeled for other editions, but it’s tougher for artists with generally impressive discographies. I like all of your picks!


      1. Yes, I saw your other posts, but I’ve never gotten into Eric Church and I’ve only heard a few songs from James McMurtry, but I’m really looking forward to a Sunny Sweeney one – I can easily come up with a top 15 for her!

        Liked by 1 person

  3. Great read, Zack. A few scattered thoughts:

    -You make a very insightful observation regarding “I Hope You Dance” in that there’s an element of uncertainty in Womack’s plea to her daughter. You’re right, a parent can try to influence a child’s decisions in the journey through life, but it’s ultimately out of their hands. I’ve been listening to that song since it was released and have probably heard it hundreds of times, but I’ve never picked up on that aspect.

    -As much of a diehard Rodney Crowell fan I am, Lee Ann’s version of “Ashes By Now” blows his away.

    -I know this is going to be shocking, but I’m a weirdo who’s never really been able to get into “Does My Ring Burn Your Finger”, one of her most traditional songs, and can’t explain why. Everyone considers it to be one of her best and I’m like *shrug*, lol.

    -“I Think I Know” totally, uh, activated my “allergies” the first time I heard it. What a song.

    -It’s been so long – at least a decade – since I listened to There’s More Where That Came From front-to-back. I absolutely need to rectify that. I don’t remember if I’ve ever heard Something Worth Leaving Behind (the album), but I do love the title track, pop production or not.


    1. Thanks, Andy!

      First of all, I didn’t want to admit in the post itself, but yeah, I do think her take on “Ashes By Now,” and I’m a big Crowell fan myself!

      Regarding DMRBYF, that’s totally fair. We all have those songs, albums and artists where we veer from the consensus and can’t place our fingers on why. It’s just a personal thing at the end of the day, and Lee Ann has the type of versatile discography where that can easily happen. Totally get where you’re coming from!

      Glad I’m not the only one who’s even heard of “I Think I Know,” much less likes it, btw. A lot of people didn’t like it when it was new I don’t think, but I can’t help it. I love it!

      I didn’t include anything from SWLB, but I do really like the title track.


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