This will likely be the first time I’ve walked into one of these features without possessing a deeper personal context behind the artist that I’m exploring in detail.
Really, with Patty Loveless, the main talking points are easy anyway. She’s an Appalachian and distant cousin of Loretta Lynn who garnered immense critical respect in the 1990s for a career built on songs that carefully balance contemporary and traditional stylings. On that alone I’m always inclined to compare her with Alan Jackson, possibly my all-time favorite artist. And yet unlike Jackson, I can’t say I grew up with Loveless’ music in the same way I did with his 2000s output. While he exploded in popularity at the turn of the decade, Loveless had largely faded – at least on radio – by the late ‘90s, and that’s a real shame and, sadly, a somewhat early sign of how women in country music would go from having their best decade in country music to having their worst one … that is, until the 2010s.
Credit to her though, because while she’s got an amazing run of singles – of which we’ll get to – she’s also got several near-classic albums under her belt in When the Fallen Angels Fly and Long Stretch of Lonesome. And that’s before mentioning that, when the hits dried up, she didn’t try courting radio; she made an amazing bluegrass project in Mountain Soul and focused her attention on covering awesome classic country songs later in the decade … before essentially retiring and ending on a sequel to Mountain Soul that’s still good, but feels lacking for a grand finale.
And yes, hearing her on Carly Pearce’s “Dear Miss Loretta” earlier this year is essentially what prompted me to explore Loveless for this feature, but I will be honest and say that my deep-dive into her music only started a few years ago, and while I’ve heard everything a few times over, this is one list that fluctuated wildly while making it. She’s arguably the most consistent artist pretty much ever in country music, enough to where I had to whittle this down from an original list of 40+ songs! And I thought the Dwight Yoakam list was difficult …
Anyway, let’s get to what you all came to see. Here are my 15 favorite Loveless songs. Be sure to let me know if you have any favorites in the comments below.
No. 15, “My Heart Will Never Break This Way Again” (written by Gary Harrison and Matraca Berg)
2000’s Strong Heart tends to get overlooked in Loveless’ discography, but it features some of her best and most underrated material, and this spot could have easily gone to “The Last Thing On My Mind.” As the first selection on this list, though, it’s the first example of a running theme in the songs Loveless chose to record – an inspired confidence that either comes all too naturally or has to be found, like here. Between the downbeat yet accentuated thicker acoustic strumming and traces of melancholic pedal steel, reverb, and a perfectly timed fiddle solo, this is a track that finds the silver lining in a bad breakup by noting that not only will time heal the aftermath, but that Loveless’ character will love again, even if not for a while.
No. 14, “Timber I’m Falling in Love” (written by Kostas Lazarides)
If there’s another running theme of Loveless’ work, it’s usually one of loss, where the main appeal and difference comes down to how Loveless copes with it. Not here, though. In fact, it’s one of her few relentlessly upbeat songs about falling in love to begin with, and could easily be seen as the next step or sequel to a good portion of her recorded output. She has a strength for ballads, but between the jangly rollick of the acoustic strumming and bouncy touches of dobro, this is a deliriously catchy ode to love that predates Shania Twain, and that’s a compliment. The other hidden strength? Vince Gill on harmony, y’all.
No. 13, “You Can Feel Bad” (written by Matraca Berg and Tim Krekel)
Another upbeat and melodically strong selection following the last one, only this time around Loveless is having too much fun piecing her life back together, that she doesn’t have time for a whiny ex-lover trying to guilt-trip her back into his arms. And since I don’t have much to add beyond that, I’d like to point out how tightly woven her material is on a purely compositional level, enough to where that fiddle slyly sliding its way under the chorus is an added strength to making an already catchy song stand out with so much life and vigor behind it. Her ex-significant other may feel bad, but it’s hard not to feel good listening to this.
No. 12, “Keep Your Distance” (written by Richard Thompson)
As I noted in the introduction, Loveless had some late-career gems, and though 2005’s Dreamin’ My Dreams, like 2008’s Sleepless Nights, is mostly characterized by covers of classics that don’t always work as well as the originals, this is a huge exception. It ditches the ‘90s polish for something much punchier and bolder in its presentation, enough to where I’m surprised Marty Stuart didn’t produce this. And while it doesn’t capture the ragged edges of the Buddy and Julie Miller original, I’d argue that Loveless’ more straightforward and biting delivery suits it better anyway. “Keep your distance” comes across more like the threat it was meant to be.
No. 11, “The Grandpa That I Know” (written by Shawn Camp and Tim Mensy)
Another late-career gem, but also one that comes with a more loaded context, in that this is about a child’s first brush with death. Yet instead of framing it as sorrowful or even around the mystique of death itself, this lets a child’s innocent perspective see their grandfather’s passing as what it should be – not a goodbye, but rather a celebration of who they were on Earth. And as someone who’s lost his own grandparents within the span of a year … yeah, I’ve leaned a lot on those memories and get what this is going for, and it’s an absolutely beautiful tribute to life itself.
No. 10, “Ships” (written by Gretchen Peters)
I’ve loved this song for a few years and am only now discovering that it was written by Gretchen Peters, which for me is already a huge plus. And it’s so obvious now hearing it, from the warm and textured production that’s tempered without being lacking and actually carries a lot of weight in trying to frame two people jaded by love yet willing to drop their guards upon meeting each other. And I like that it essentially frames them as two polar opposites who find that connection anyway: Eddie’s a drifter who’s too free-spirited to settle down and Lillie is stuck in a dead-end job but wants to find stability; both are way past their primes in life but finally find their ships have come in, and that’s a love story worth rooting for, indeed.
No. 9, “Nothin’ But the Wheel” (written by John Scott Sherrill)
It’s at this point where I feel like I’m repeating myself reiterating Loveless’ greatest strengths as an emotive interpreter, especially on a beautifully tempered ballad about hanging on in the immediate aftermath of a breakup that comes naturally to her, enough to where I’m baffled that this never took off at radio. I shouldn’t have to call it underrated when working with her catalog, but alas, it’s still a beautiful song, and a rare moment where Loveless doesn’t look ahead with optimism so much as hang on … and to more than just a steering wheel, at that.
No. 8, “On Your Way Home” (written by Matraca Berg and Ronnie Samoset)
Speaking of beautiful ballads that country radio ignored, while Loveless has some excellent kiss-off tracks that are a lot of fun, there’s arguably none better than this cutting track in which she gives a presumably cheating lover all the grief he deserves. And yet it’s still a slow burn, and not just in the ragged production that highlights some excellently burnished textures in the guitar and fiddle work, but also in the questions asked both of that significant other and Loveless herself. From questioning how it came to that moment to playing coy as she asks questions of his infidelity knowing the answers already, to then questioning herself about her own next move to make. Absolutely bitter and sad, Loveless has always known how to best capture characters broken to their core and make them sadly relatable figures.
No. 7, “Here I Am” (written by Tony Arata)
Another slow burn, though unlike “On Your Way Home,” this is a takedown that Loveless isn’t there to actually witness or spur, instead acting as something of an outside narrator to depict her ex-significant other’s increasing alcohol abuse. But it’s much sadder than even that, if only because she wishes she could be there to try and stop him, knowing that he’ll never drink enough to get her off of his memory yet try anyway. And while she’s not responsible for his mental well-being, it’s still heartbreaking to watch someone you still love decay into a former shell of themselves. Loveless is arguably the queen of modern heartbreak in country music, and it’s because of morally complex framing on songs like this.
No. 6, “You Don’t Even Know Who I Am” (written by Gretchen Peters)
Thus far my favorite Loveless songs have succeeded by exercising restraint, but my absolute favorite moments in her entire discography are the ones where she swings for the fences and delivers a soaring vocal to match the emotion on display within the content. And the funny thing is, this isn’t a story of one partner leaving the other – which Loveless would have absolutely nailed, for the record – but rather a clear-cut and even-sided portrayal of how two hearts fall out of love, sold with so much conviction from Loveless, that the huge performance may not depict two angry people coming to blows with one another, but rather two people finding the saddest sort of escapism.
No. 5, “You Don’t Seem to Miss Me” (written by Jim Lauderdale)
Funnily enough, this is the one-sided perspective of “You Don’t Even Know Who I Am” I said Loveless could easily nail in my previous blurb – and she did, similar titles and all. Only instead of writing off a love long dead, Loveless brings such an immediacy and urgency to her delivery absolutely brimming with energy to try and save what’s left … while also launching any and all necessary barbs at a neglectful lover to get that point across along the way. Also, it features George Jones on harmony vocal, and if you want yet another example of how cool Loveless is, when radio programmers asked for a remixed version of this that didn’t feature him, she stood her ground, and what could have been a smash No. 1 hit instead was a meager top 20 hit. No matter, because as we’ve seen today, it’s not like the biggest hits on the chart dictate quality anyway, and this is a song in Loveless’ discography that absolutely feels like a true moment.
No. 4, “Too Many Memories” (written by Stephen Bruton)
This one snuck up on me when revisiting Loveless’ albums, a deep-cut from 1997’s underrated Long Stretch of Lonesome. I think it’s just how that melancholy lingers off of the melody, understated piano chord, warmer brushes of acoustics and percussion balanced against the burnished electric guitar tones, and drawn-out chorus that really sells it for me. But there’s a deep richness to the content, too, framed around an older person’s perspective left to spend their final years alone with nothing but their memories. And while the usual approach is to frame those memories as assets that can provide a link to the past, sometimes they act as painful reminders of what was and what never will be again. It’s a valid and overlooked perspective executed excellently here, especially when age and time only grants us more memories to desperately hang onto, for better and worse. An incredibly strong and moving song, and one that deserves so much more attention as far as Loveless’ work goes.
No. 3, “Long Stretch of Lonesome” (written by Gary Scruggs and Tony Arata)
I’m imaging an alternate timeline where, in the wake of country music’s move toward crossover-ready power ballad territory in the latter half of the ’90s, Loveless and her team release this as a single and it completely revitalizes her career. Granted, we might not have gotten Mountain Soul then, but come on, this is easily her best portrayal of optimism in the wake of a breakup, where the main appeal boils down to, “listen to her sing that chorus and you’ll get it.” The thing is, with the lusher strings and burnished touches of the production, this is definitely among her bolder ballads, and the pure heart and soul of country music simply shines through in the pure emotion on display. It’s a perfect ballad that proves Loveless could have carried country music into the 2000s, and it’s a damn shame she never got that chance.
No. 2, “How Can I Help You Say Goodbye” (written by Burton Banks Collins and Karen Taylor-Good)
This is an easy No. 1 on a lot of other “best of” lists for Loveless, and I get why. Of all of the ‘90s songs to play around with the concept of having their titles carry different meanings with every verse and chorus (the “Where’ve You Been” effect, in other words), this is one of the finest. A song that tries to capture the winds of change in multiple ways, from saying goodbye to childhood innocence, to having to grow up and face the hard truth that love doesn’t always work out, to having to say goodbye for good to the person who taught you how to say it in the first place, “How Can I Help You Say Goodbye” works because of its simplicity. It resonates because we all understand her frustration even when we can’t directly relate to it at the current moment in time, because we remember the sting of how hard that one word can be to say or express. And the underlying message is that goodbye doesn’t have to actually signal an end, but rather a way to place distance between a past hard time and a present day in which we can look back with fondness having now been healed. That feels weird to say coming off of my discussion for “Too Many Memories,” but as an optimist myself, this resonates just a little more for me. For as much as I’ve (rightfully, in some cases) complained about Loveless’ greater lack of exposure at country radio, this is a five-minute ballad that became a top five hit, and that’s an accomplishment, indeed.
As always, before I discuss my No. 1 song, I’d like to throw out (more than) a few honorable mentions, especially this time around:
“To Have You Back Again” (written by Annie Roboff and Arnie Roman)
“When the Fallen Angels Fly” (written by Billy Joe Shaver)
“The Last Thing on My Mind” (written by Al Anderson and Craig Wiseman)
“That’s Exactly What I Mean” (written by Kim Richey and Tia Sillers)
“Out of Control Raging Fire” (feat. Travis Tritt) (written by Kostas and Melba Montgomery)
“Lonely Too Long” (written by Bill Rice, Mike Lawler, and Sharon Vaughn)
“Hurt Me Bad in a Real Good Way” (written by Deborah Allen and Rafe VanHoy)
“Blame It On Your Heart” (written by Harlan Howard and Kostas)
And now, my No. 1 pick:
No. 1, “You’ll Never Leave Harlan Alive” (written by Darrell Scott)
I’ve never been a believer that artists need to write their own material in order for it to be valid. That’s a stupid and tired argument with several flaws and an ugly elitism to it that I just can’t stand. And so when I say that Patty Loveless has easily recorded the definitive version of “You’ll Never Leave Harlan Alive,” I not only attribute it to her delivery, but also her believability as an interpreter and her understanding of the content, given how this song is hauntingly similar to her own upbringing in Pikeville, Kentucky. And while the recent proliferation of independent country singers working within very regional circles trying to capture rural life from everywhere to Georgia to Kentucky and beyond would have you believe that this an overused topic, in truth, around the early 2000s it became a forgotten one, which in part is what helped spur a roots music boom around the time.
This has always been my pick for the crowning moment of that time, too – a starkly written and frankly depressing tale of trying to make it in Harlan that’s constantly brimming with tension and desperation, pushing otherwise good people to their breaking points and then beyond them to succumb to hopelessness. The characters are filled with detail, framed through an empathetic lens as a sad ode to those forced to return to the mines for mere survival, with Loveless’ bone-chilling account to carry it all. And as if I needed anything else to push this perfect moment off of Loveless’ “back to her roots” project even higher, there’s an extended, very meticulously drawn-out solo that carries this song out and lets that despair hang by a thread, as it, unfortunately, has to be. I admit I first heard the Brad Paisley version and held that dear to my heart for years – and if I ever make a feature for him, expect to see it again – but this is, without a doubt, the superior version. It’s my favorite Loveless song, and one of my favorites of all time.