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Fifteen Favorites: The George Strait Edition


Photo credit: Maxine Helfman, of The New Yorker


It just feels right to ring in the new year with a George Strait retrospective.

After all, very few artists have crossed generational divides quite like George Strait. And even then, very few have crossed them as uniquely as he has throughout the years. Well, decades, I should say. That’s the magical thing about Strait – whether you grew up through his initial ‘80s rise, his continued ‘90s and 2000s run, or even his quieter run in the 2010s (heck, maybe even this decade, given his legacy status), he was there and on top of his game, and chances are there are many of us who can say his music soundtracked our childhoods.

And yes, his contributions to the early ‘80s neotraditionalist movement are worth noting toward his rapid rise that stood in sharp contrast to the slicker-produced Urban Cowboy material of the time. But the reason he’s endured? Well, to me, it’s a myriad of factors. He’s consistent, he’s picked songs with some subtly excellent melodic compositions and hooks that stick around, and he’s middle-of-the-road. I don’t state that last point in a bad way, either. Sure, some of his material is soft – running back through his discography again reminded he was never much of an album artist, even if, oddly enough, many of my favorites by him are forgotten album cuts. But there’s an easy warmth and simplicity evident in the bulk of his material that makes it all easy to return to and go down smooth; he’s arguably the best singles artist to ever grace the genre.

But in a weird way, the songs featured here today oddly don’t characterize personal childhood favorites. So if you don’t see the usual classics featured, that’s why. It’s an oddball way to go about discussing a straightforward artist, but I think it goes to show just how deep his catalog actually runs. So without further ado, let’s get started.


No. 15, “Lefty’s Gone” (written by Whitey Shafer)

Let’s get this out of the way before it becomes an issue: George Strait didn’t write the bulk of his material. And that’s OK, because as I’ve stated before, artists can craft their own unique identities through other means, be it through their sound or presentation style. This tribute to Lefty Frizzell, then, feels as essential to Strait’s point-of-view as it does to songwriter Whitey Shafer’s, but it’s also the rare cut in his discography that feels … uncomfortable. Intentionally awkward, if anything, especially as it’s evident just how hard Strait is trying to fight through a somber tribute to an artist who sang equally somber songs and met his own tragic end. “I heard he was sad and lived alone” / “It’s not right, but Lefty’s gone” – the delivery alone of those lines secured its place here.

No. 14, “You Haven’t Left Me Yet” (written by Dana Hunt Black and Kent Robbins)

The weird thing you might not know about or expect from Strait? He’s got some excellent album closing tracks, many of which comprise this list. Oddly enough, this is another track I could describe as somewhat awkward with its choppy yet catchy melody, but that only feeds the quirky, quintessential twist of that hook quite well – that being how while Strait’s character’s significant other has left him physically, she hasn’t left his mind, only subtly amplified by the faint, echoing backing vocals. So he goes about his day trying to forget and knows he needs to move on, but can’t. It’s a concept and execution I’ve heard employed in similar songs, but it’s one I can’t help but always fall for, the hapless character just trying to put the pieces back together … even if in vain.

No. 13, “By the Light of a Burning Bridge” (written by Walt Aldridge and Michael White)

Of course, there’s trying to put the pieces back together in vain, and then there’s finally finding clarity after a hard-fought battle. No, there’s not a lot of outright struggle in Strait’s songs, but there’s still a sense of restrained, rollicking optimism in both his delivery and the spacious keys and chipper percussion patter I just love here; enough to suggest the newfound perspective here is lived-in and earned, at least. Like contemporary and fellow neotraditionalist Alan Jackson, I feel that Strait’s material has aged gracefully over time. His delivery is deeper, fuller, richer, and just overall more settled as a result, and this is the type of track that fits an older, wiser perspective so effectively.

No. 12, “She Took the Wind From His Sails” (written by Dean Dillon and Donny Kees)

I’m not sure if this has always stuck with me due to my love for nautical-themed songs, the calming melody anchored in a lot of sweeping liquid texture off the faint echoes and touches of mandolin playing off the acoustics, or the straightforward but surprisingly sad story. It’s because of every one of those elements, of course, a love story of two-liked minded people – soulmates, naturally – that ends in tragedy but not without something – someone – to show for the time together. Either way, it’s a trip across water I’m always happy to embark back on, time and time again. A simply striking gem nestled deep within.

No. 11, “House of Cash” (feat. Patty Loveless) (written by Leslie Satcher and Monty Holmes)

This is about as nasty and grimy as Strait gets, what with the more blusterous electric axes and fiddle playing surprisingly well off both his and especially Patty Loveless’ huge deliveries in what is, ostensibly, a sendoff to an iconic country music landmark – Johnny and June Carter Cash’s lakeside home, destroyed in a fire in June 2007. It’s a song where understanding the breadth of history helps in capturing its legacy – the same place where Cash wrote most of his famous music, the place where “Hurt” was filmed, and the place where Kris Kristofferson once landed a helicopter on the front lawn to pitch some songs – especially in understanding the almost serpentine-like solemnity both artists offer this song in stating how no one was ever meant to ever grace the same abode after its most famous residents left it. The ring of fire comes full circle, indeed.

No. 10, “Troubadour” (written by Leslie Satcher and Monty Holmes)

I noted before that time has only deepened Strait’s delivery and the wisdom he’s able to both impart and sell. And when you’re on your third decade as an entertainer, that self-reflection feels all the more necessary, both to take stock of what’s been accomplished and what’s left to do. Another rare weighted moment in his discography he sings as if he wrote it, adding a somber yet accepting tone to the song that’s fitting enough to be called a personal anthem anyway. He’s not an old troubadour gone just yet … more just one finishing up the next chapter of one of what has been country music’s best stories thus far.

No. 9, “You’ll Be There” (written by Cory Mayo)

And from “Troubadour” we turn to, well, another late-career reflection, this time around one that tackles complex issues of faith and religion and settles deeper for me with every passing year. This time, too, it’s a reflection told from the perspective of an ambiguous character who ponders the end and wonders what waits afterward. Now, just stopping the description there … I could see where this could possibly stray off course by becoming too preachy. But the beautiful part of “You’ll Be There” is its childlike innocence and beauty in the pure wonder of the unknown great beyond, showcased best in Strait’s delivery but also in its constant questions asked as well as the beautiful swell of strings and backing vocalists that only build to greater heights as the song progresses. It’s a huge song that matches it in tone step-for-step. And for me, songs that can tackle this topic and question in a way that could include everyone – sinners, saints, and fools alike – are the ones where I find the most personal resonance. It’s a late-career highlight that tends to get overlooked, but a marvel to behold, all the same.

No. 8, “Run” (written by Anthony Smith and Tony Lane)

There’s something to be said for much Strait can make a contemporary sound work heavily in his favor, even despite being known for eschewing that in favor of a more down-the-middle presentation. Maybe it’s that smooth, soft-spoken delivery helping it, but there’s a glistening transcendence and liquid sheen to some of his 2000s material I can’t help but love in playing well to broader sentimentality.

And that goes especially for the mysterious “Run,” where we never know exactly why Strait’s character’s partner has left, other than to possibly just chase their own wanderlust. But the fact that his delivery is rather heavy and vulnerable with a driving sense of urgency makes me think it’s all just wishful thinking on his part for a reunion that will only take place, at best, in his mind, only further bolstered by the alluring, spacious keys and liquid pedal steel – a melancholy that can both envelop and establish a scene and then linger about it. Or maybe it is just simple longing for someone who’s also itching to find her way home as well. Either way, it’s a beautiful song that’s always stood apart in Strait’s discography.

No. 7, “Living For the Night” (written by Dean Dillon, Bubba Strait, and George Strait)

Continuing on with regret and heartbreak wrapped in lovely strings and liquid textures, we have my underdog pick for a favorite Strait single of the 2000s entirely. Still an outlier in its own right, however, given that it’s another oddly dark and polished cut than what he’s actually known for, which actually comes as a surprise, given that this is one of the few hits he’s co-written. Call it another case of Strait’s hugely emotional delivery just really underscoring a lot of why I love this, then, because despite being a far moodier and more contemplative effort – especially in an ending conceit where he doesn’t find clarity, but only mere escapism – I still think this works well within his wheelhouse. It may not go down as an especially remembered hit, but it deserves to, at least to me.

No. 6, “Meanwhile” (written by Wayland Holyfield and J. Fred Knobloch)

This is a Strait single I’ve always underrated. Even when revisiting it in a recent edition of my Favorite Hit Songs series, it didn’t crack my top ten. But for some reason lately it’s the single of his that’s entered my head for no reason at all and won’t leave. And I guess I can now see why, given that it plays to a lot of traits I typically like about Strait singles. It’s sweeping in a lot of hugely gorgeous textures off the fiddle and strings in playing to that huge hook, right down to a key change that I swear truly makes this song. And, like “You Haven’t Left Me Yet,” it’s another song that finds a hapless character in denial over a wonderful past that doesn’t reflect a current reality, where he’s free to replay past memories of a relationship now dead as many times as he pleases, because he’ll never relive the feeling in actuality. But hey, sometimes confronting the bittersweet memories helps find temporary levity, and at least here, that’s enough.

No. 5, “Marina Del Rey” (written by Dean Dillon and Frank Dycus)

I mean, what can I say? Sad Strait is my go-to jam, and off a run of songs I just spotlighted in which he plays to that exact territory, it’s good to go nearly all the way back. “Marina Del Rey” was a bit of a surprising sonic pivot coming from the same artist who brought fiery honky-tonk numbers like “Unwound” and “Fool Hearted Memory” before it, but to me, it’s also the first showcase of how Strait proved he could dig deeper with something surprisingly sad and emotional. But unlike the tracks mentioned above, I think the overall fondness underscores this track a lot better than the painful reminder of what no longer is does, where Strait can run back through a memory appreciating it for what it was and what happened in a hypnotic, dreamlike sequence. It could also be that subtle great little piano lick after each chorus that gets me, too.

No. 4, “Amarillo By Morning” (written by Paul Fraser and Terry Statford)

It had to be here somewhere, right? It’s quintessential Strait, the moment where for many, he truly arrived as an artist who would grace the format for years to come. And regardless of whether we’re referring strictly to his rodeo-themed content or best songs in general, “Amarillo By Morning” remains a striking highlight. I don’t know what exactly to attribute it to, either. Maybe it’s that extended intro buoyed by sweeping fiddle and how it sets the stage akin to an early morning sunrise and the dawn of yet another day. Maybe it’s the old-fashioned, plainspoken effectiveness that would guarantee it to go on to become a country music classic, where even though the rodeo life has taken everything from this character, it’s also offered everything that constitutes as true fulfillment for him in life. Either way, it’s an undeniable career song, and the fact that it came so early on in Strait’s career truly says it all needs to, I think.

No. 3, “The Road Less Traveled” (written by Buddy Brock and Dean Dillon)

On paper, I can understand why a song about going down the evergreen metaphorical road less traveled might seem out of place in Strait’s discography. Fans know what to expect from him sonically and even lyrically, and that’s part of the appeal in general. But I don’t know – I think there are enough cuts here that justify how varied his entire catalog actually is, regardless of how it fits within the context anyway. After all, there’s so much naturally burnished potency I love about this song simply as is, from the wistful blasts of organ trading between the fantastically weathered electric axes to add just the right amount of kick to this journey. Restrained and intimate otherwise, but able to slightly ramp up the tension when needed, if only to echo the appeal of going against the grain from time to time. It’s also as good of a time as any to credit Dean Dillon’s melodic and songwriting chops, the secret weapon behind so many of Strait’s iconic singles.

But I think I appreciate the sentiment and Strait’s even-keeled interpretation even more, where he freely admits that wandering down the road less traveled “all might come together or all might come unraveled.” There are no guarantees, hence why it feels more real to Strait’s perspective of wanting to take a chance and sketch a path that will be remembered. So far, so good.

No. 2, “A Better Rain” (written by Tony Lane and David Cory Lee)

I’ve had to have heard this sometime before. It Just Comes Natural is one of those albums I grew up with and look back on fondly. I just must not have appreciated this deep cut until I revisited it yet again for this feature, because this is beautiful. By now I’ve practically established the foundation as for why: Strait’s tempered emotive presence once again plays well to a beautifully weathered sentiment, especially in the beautiful fiddle and acoustic accents.

But I think the reason it cuts deeper is the sentiment itself, where even if I may have to forgive the occasional awkward line of poetry here and there, I love that it’s built upon a relationship looking to heal itself. Not to repair itself, mind you – the conceit here is that the love here has died out, at least in a sense of togetherness. But despite whatever damage was done, Strait’s character hopes to redeem himself to the point where he can right whatever wrong dealt to his partner and help offer her a fresh start, even if it will be without him. Maybe it is all just built on wishful thinking, but it got to me regardless. It’s just so wonderfully mature and beautiful throughout, the type of song where the context doesn’t matter so much as the execution. And in this particular case, it’s certainly a cathartic rain.


As always, before we get to my No. 1 pick, here are a few honorable mentions for other great songs:

“Somewhere Down in Texas” (written by Dana Hunt Black, Tim Ryan Rouillier, and Charlie Black)

“I Saw God Today” (written by Rodney Clawson, Wade Kirby, and Monty Criswell)

“The Chill of an Early Fall” (written by Green Daniel and Gretchen Peters)

“When the Credits Roll” (written by Steve Bogard, Kyle Jacobs, and Randy Montana)

“She’ll Leave You With a Smile” (x2) (the original version written by Jackson Leap; the 2001 version written by Odie Blackmon and Jay Knowles)

Yes, he really did this.

“A Showman’s Life” (unofficially feat. Faith Hill) (written by Jesse Winchester)

And finally, fittingly enough, “The Cowboy Rides Away” (written by Sonny Throckmorton and Casey Kelly)

Plus more!


No. 1, “Drinkin’ Man” (written by Dean Dillon, Bubba Strait, and George Strait)

There are plenty of sad George Strait songs, no doubt. And there are plenty of them, like the ones listed above, where the context doesn’t matter so much as the execution. Strait’s naturally captivating pull as an emotive interpreter is often more than enough needed to fill in the blanks. But this? It’s the sole exception – the one where you can’t hide from a heartbreaking story that leaves no detail out as it slowly unfurls. And there’s also no redemption, merely the consequences of consistent stumbles that haunt Strait’s character, enough to where the desperation for change is always evident but also always out of reach, even when the stakes are as high as losing out on love itself. It’s just too much to ask of a drinkin’ man, after all.

It’s another link in a country music tradition that stretches all the way back to the beginning, but to me, it’s the right way to approach this topic. There’s no glorification of rough and rowdy ways; the characters in these situations either find a way to rise above their vices and themselves or they become forgotten ghosts and shells of themselves. Even in the former case, it’s not like old demons can ever truly be killed. It’s not the type of work one typically thinks of first when they think of a Strait, but it’s an outlier that has always struck deep, a tale of a nameless, lost character that, at least for me, won’t be forgotten.


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