This will be the first edition of this series not to come with a personal story surrounding why I love the artist in question, mostly because this is meant to fulfill a request I received in late August, one for which I am admittedly way out of my element.
I mean, I’m aware of Lyle Lovett’s standing in the greater country music story, a Texan poet following a, shall we say, “musical family tree” of other like-minded songwriters following in the footsteps of icons like Guy Clark or Townes Van Zandt … and oddly enough being one of the few to actually gain mainstream country radio traction, albeit briefly. I’ve mentioned in other posts how the latter half of the 1980s was a rare point in country music history where more offbeat and experimental acts were embraced in the decline of the Urban Cowboy era, and Lovett was one among many. And yet unlike, say, Steve Earle, who pushed more into heartland rock, Lovett was a fuller embodiment of the Texas sound itself, with a style spanning from country to folk to rock to even jazz, as evidenced by his 1989 Large Band project.
But for me, that’s about where my knowledge of his career initially stopped, and that’s before mentioning how I was even less familiar with his deep cuts or other projects in general. So in essence, this was a learning experience, and while I won’t consider a Lovett a favorite even after hearing everything by him twice in preparation for this feature – mostly due to a more off-kilter presentation and sense of humor that either really clicked with me or didn’t at all – I admire his eclecticism quite a bit. He’s a quirky performer, and while I don’t think that suits the majority of his jazz-influenced numbers, as a songwriter he will craft lines that stick with you. Which is also to say that there’s the part of me that admires how dark that sense of humor got over the course of his career, especially when the hits dried up and he embraced being an even more creative force within the industry. He was embraced by adult alternative radio, VH1, and even as an actor. I’m a fan of the ballad-heavy Joshua Judges Ruth, but 1994’s I Love Everybody is an album that I describe more as an experience above anything else. It’s so strange, that I’m not sure whether I love or hate it; I simultaneously want to hear it again and never want to revisit it. From there you have the more beloved Road to Ensenada, a more accessible, yet no less compelling, release. And while he mostly took to recording other songs by Texan poets later on his career, I’m a fan of the original and warmer My Baby Don’t Tolerate from 2003.
Yet, I think what I find strangest is that, while looking for a more definitive and straightforward piece on his history in preparation for this piece … I couldn’t really find one. He started slowing down around the mid-2000s, and with 2012’s Release Me being his “latest” release, there’s a part of me that feels like maybe he hasn’t gotten his proper due after all. Not to say that this piece will or is meant to fulfill it, but you all know what you’re here for – a rundown of my 15 favorite Lovett songs. Keep in mind, again, that while I did my due diligence and listened to everything I could, this, of all the lists I’ve done for this series, is by no means meant to act as a definitive guide for Lovett’s music. The majority of what I heard is still new to me. Again, too, he’s eclectic, so what did and didn’t work for me may or may not work for you. Some albums of his are underrepresented while some aren’t represented at all; it happens.
Enough blabbering, then. Let’s get started!
All songs written by Lyle Lovett unless otherwise noted.
No. 15, “Walk Through the Bottomland”
Here’s the thing I want to mention first before I unveil my other selections: Lovett’s songs are either presented as straightforward character-driven stories with so much vivid detail attached to them, or as complex musings on the inner psyche that aren’t so much personal as they are revealing of everyone involved. This falls into the former camp, a tale that might as well be described as Garth Brooks’ “Rodeo” before it was a thing, only more focused on the growing riff and inevitable end of a couple torn between their passions. It’s just a phenomenal slow burn drenched in richness, from the accompanying pedal steel in the low-end to Emmylou Harris’ backing vocal contributions to add just enough distant realism to a heartbreaking song.
No. 14, “Simple Song”
This is one of those songs I would have expected to hear on a late-career album rather a sophomore one, an examination of an artist’s inner psyche that, as to be expected, is abstract in its delivery and presentation. But like the title suggests, the true meaning is pretty simple – a reminder that beauty comes from within rather than what’s projected, and that how we, as listeners, interpret an artist’s message says as much about us and our views as it does their own. “Remember part of me is you,” a final line meant to linger. Personal yet universal, it’s a song meant to be uncomfortable, even before the moodier piano and cello interplay creeps in to let this reminder hit with its greatest impact.
No. 13, “Closing Time”
No, it’s not the Semisonic song, nor is this ode to last calls even directed at the bar patrons in general. It’s a wistful ode to the employees left to close the place down and watch a riotous evening settle down to the evening calm the song greatly captures in the quaint acoustic and piano accompaniment. I’m not sure there’s a deeper meaning beyond that, but it’s just a wonderfully warm portrait of a common scene that focuses on its aftermath, and also has its fun recounting the night’s events, too. Heck, it’s less of a song for bar employees as it is the introverts more comfortable with the stillness of the night than engaging in the rowdier social events it offers, hence why it’s on, you know, my list.
No. 12, “I Think You Know”
If you read my lengthy preamble, you know my thoughts on I Love Everybody, by far the strangest listening experience I’ve ever had. It’s like Lovett tried to capture Roger Miller’s zaniness and went even more abstract and darker in the process. And you’d think a song in which an old man offers advice to a younger person wouldn’t be that far-fetched; it’s practically an overdone and cliché topic in country music. And then there’s “I Think You Know,” where the best I’ve been able to interpret said advice is just … to keep your eyes open and always stay in search of the truth, questioning everything along the way? Yeah, it’s a mindwarp, and one where I can honestly say the emotional resonance is more of a primal one that comes off of the rougher waltz cadence carried its very ragged fiddle play at the front of the mix. Perhaps not as pretty as his other ballads, but sometimes the deeper truth needs to be a little more jagged and complex to get its point across. I think you know what I mean.
No. 11, “Church”
And now, we’ll go from ultra-serious to ultra-silly, where the main gimmick of this gospel song that goes all in on it with the backing vocal contributions, handclaps, and piano, is to find Jesus … only, at home rather than Church, because everyone in attendance has been there long enough and just wants to get home for dinner and eat already, damn it! It’s so earnestly overblown in getting its point across, to the point where the churchgoers receive what they believe are signs from God that it’s OK to go home after all. Perhaps a little overly self-indulgent and overlong – another element of Lovett’s work that can be hit or miss – but this is too fun and genuinely infectious to care that much.
No. 10, “North Dakota” (written by Lyle Lovett and Willis Alan Ramsey)
This is a combination of the best of both worlds I alluded to when discussing “Walk Through the Bottomland.” Beyond the pure windswept beauty of the song, what I love about “North Dakota” is how it’s both an examination of the cowboy persona by delving into its naturally lonely and aimless nature, at least in the first half, as well as a love song by its second half. More than that, though, it’s a song about losing love from Lovett’s perspective, with the implication being that he was once that starry-eye dreamer who traveled the world looking for thrills … and likely chased them to the very end, even after finding what he was truly looking for to begin with, with the song acting more as a lesson to other cowboys than a story about them. Beautiful stuff, and obviously not the first time I’ve basically said that here, nor will it be the last.
No. 9, “Loretta” (written by Townes Van Zandt)
There’s two covers here that I feel transcend the originals, and ironically enough, neither of them come from Step Inside This House. No, they both come from 2009’s Natural Forces, another project indebted to famous Texas songwriters, but one that’s a little more cohesive and well-rounded as a whole. When you pair Lovett with a Townes Van Zandt classic that aims for a warmer country palette in the terrifically warm fiddle and piano interplay that became something of a hallmark for his work in the 2000s – of course it comes across excellently. There’s such a full-bodied richness to the tones here. It also helps that both vocalists have the same craggy weariness in their vocal tones to better support the road-weary journey of finally finding love in a partner who can settle you down … but also live just as hard and fast as you, too. It might be cheating to say this just works on a basic level, but it’s good enough for me.
No. 8, “This Old Porch” (written by Lyle Lovett and Robert Earl Keen)
This is a song where the background surrounding its writing transcends the song itself, a tale that acts as an extended metaphor for the first time Lovett and Robert Earl Keen met, and belongs more to both artists than it does to either one individually. But to have a place on this specific list, the song has to stand on its own, and it does. But it’s also one that goes beyond a moment in time, an ode to friendship and memories shared between two writers within the titular setting, but also an ode to how they would have to inevitably move on to follow their own journeys, always able to return to each other through those memories. It’s celebratory in a way that predicted how both artists would have their own respective times to shine, but also wistful and sad knowing the best days of that journey aren’t the ones where success was earned, but rather the ones where it was just another hunger to satisfy … especially with a friend who shared and understood the same starry-eyed sense of wonder.
No. 7, “If I Had a Boat”
I think what I love most about my favorite Lovett songs is how deceptively nostalgic they are – not in the traditional sense, mind you, but rather in the way he captures childlike wonder from a grown-up perspective. And considering this is one of his most well-known songs, it’s no wonder why that resonates with listeners beyond just an earnestly chipper presentation. Yes, it’s nonsensical in trying to get there, but that’s part of the point in trying to frame this as written by a child. Granted, we’ll never recapture that magic again for ourselves, and how we achieve something even close to that now for ourselves is more chemically induced than anything else, but hey, we can try and dream, even if that desire is sailing the waters with a damn pony onboard.
No. 6, “The Road to Ensenada”
Sometimes great songwriters craft even greater songs by forgoing the details and letting the pure emotion resonate instead. That doesn’t make much sense, I know. But every time I hear this I leave with more questions than answers and yet, am satisfied anyway – a tale of a man dying, presumably in Mexico but of what, we never know. It’s more like his dying declaration of hoping to see someone again who never comes, most likely because this is him sifting through memories of a past life before the end. And though we don’t know much about this character, we know enough to sympathize because he could be anyone – a drifter who had his own experiences in life and clings to memories before his unfortunate, but inevitable, end; a purposefully unfinished story resonates nevertheless. It’s not Lovett’s grandest adventure, musically. It’s sparse, but in a way that reflects the dying breath of a character who begs for mercy. I know enough to know he deserves it.
No. 5, “Private Conversation”
This is the ‘90s country jam that, in an alternate timeline, would have at least helped dominate the decade. Instead, it’s another gem off of Lovett’s most well-known album, The Road to Ensenada. Yet, beneath the veneer of a bright and buoyant melody anchored by that great fiddle work, this is a dark cheating song. And considering the main point is to show how two people can so easily fall into an affair without considering the consequences or who they’ll become afterward, the normalcy of the presentation is part of the point. I’m going to unironically call it sinfully catchy, because that says it best anyway.
No. 4, “Pontiac”
This song kind of blew my mind the first time I heard it, arguably Lovett’s darkest song of his career, and also one of his shortest. I’m glad it is, because of the many country songs to explore a soldier’s PTSD as the character returns home, this is one that explores it from that soldier’s point of view decades after the fact and cuts things off before the details become even grimmer than they already are. It’s a slow burn in every way, from the lingering, melancholic piano and string accompaniment that echoes the mental anguish and pure exhaustion felt by this character for far too long, where everything has essentially burned away for him as the pressure becomes too much … and as for what he actually plans to do about it, we’ll never know, even if we kind of do, unfortunately. I rarely feel emotionally drained listening to something, but this is absolutely an exception.
No. 3, “Whooping Crane” (written by David Eric Taylor)
This is the other cover here, but also one where I’m less inclined to compare it to other versions and instead appreciate how this song received a deserved second shot at life. It’s a powerful message, so that echo is needed and appreciated. In essence, it’s one of the best environmentally minded country songs next to John Anderson’s “Seminole Wind,” noting the destruction of the natural resources we inherited from Native Americans, and how that destruction is two-fold in its decimation of property and note of how we’ve treated them throughout history, all for the sake of … progress, I guess. Whatever that’s supposed to mean. I’m not going to say Lovett is a technically stellar performer, but he knows how to sell weary rage and desperate frustration with the best of ‘em.
No. 2, “That’s Right” (written by Lyle Lovett, Willis Alan Ramsey, and Alison Rogers)
OK, for one, it’s deliriously catchy, but it’s also self-aware of Texas pride enough – in music but especially within the general culture – to know it can be seen as insular to the point of gatekeeping or “othering” outsiders. So during a chance encounter with a total stranger, Lovett basically says to hell with it and accepts them anyway because … why not? It’s a song where he’s aware of Texas history and proud of it and what it means, but to the point where he’s excited to share it with others rather than keep it all to himself. It’s just such a refreshing perspective, and as someone with family who used to live in Texas, it hit a more personal note for me. But come on, it’s a western swing number that’s incredibly delightful and cheery. It was nearly my favorite Lovett song, but there’s just one more song that hits a little deeper for me.
As always, before I reveal my No. 1 selection, I’d like to run through a few honorable mentions that just barely missed the cut for this list, presented in no particular order:
“Isn’t That So” (written by Jesse Winchester)
“She’s Already Made Up Her Mind”
“My Baby Don’t Tolerate”
“Farmer Brown (Chicken Reel)” (written by Lyle Lovett / traditional)
If this didn’t inspire this Cyanide and Happiness skit, something is terribly wrong with the world.
“Nothing But a Good Ride”
And now, my No. 1 selection:
No. 1, “In My Own Mind”
No joke, before I embarked on my Lovett deep-dive, Andy told me about his own experiences with Lovett’s music, in turn mentioning My Baby Don’t Tolerate and one particular song off of it that he noted as a personal favorite of his. So I started with that album, and when I get to the song he referenced, I knew it would be the song to beat for me as my favorite Lyle Lovett song. Lovett rarely got personal, so to say, but if you really read between the lines of, well … any of these selections, I’ll repeat what I said about “Simple Song”: it’s amazing what our interpretations say about us. As such, with “In My Own Mind,” a quirky songwriter penned an ode to himself that I think ended up being a quiet anthem for introverts everywhere. It’s a song I’d best describe as tranquil and content, not only off the warmer, low-key brushes of pedal steel and fiddle off the piano that give this track its graceful exuberance, but also in its simplicity of retreating to the country or just someplace quiet to find silence and inner happiness … and maybe peace along the way. And as someone who understands that far too well, this is the song that convinced me to look for the deeper connection within Lovett’s music. And as one of the first steps of that journey, this will go down as an all-time favorite for me. In my own mind is a weirdly wonderful place to be.