Favorite Songs by Favorite Artists: Gary Allan

I hate to throw around the word “authenticity” – it’s been used to fuel a lot of unhealthy conversations in country music – but I always knew Gary Allan’s pain was the real deal when I listened to his material. Granted, there was a certain point in his career where it became nearly impossible to separate the artist from the art at hand, and has since shaped his outlook and approach to the music-making process. Even before that unfortunate incident, though, I always found Allan’s vocal presence to be magnetic – he was an artist who didn’t seem to understand the world around him or his place in it. As a teenager, I understood that. His music, then, shaped a very formative part of my life.

Now, what really makes him one of my favorite artists of all time is the incredible album run that began with 1999’s Smoke Rings In The Dark and ended with 2005’s Tough All Over, because, my God, what a run. And while my Alan Jackson feature took an incredible amount of time to narrow down and revise, this list fell together much more quickly. I wanted to include “As Long As You’re Looking Back,” “Right Where I Need To Be,” and “I Think I’ve Had Enough,” but I’m not sad they missed the cut, either – if only because this list is incredibly strong in its own right. And since I have a tendency to ramble on longer than my Country Universe colleagues, let’s get this show on the road.

Gary Allan Alright Guy


Man Of Me

Alright Guy (2001)

Written by George Teren and Rivers Rutherford

It’s silly, it’s a bit overblown, and yet it’s all sort of the point – all that swagger on display is used to show what a wild, reckless “bad boy” this character was until he … found love. It’s an interesting spin on this sort of this song, and I’ll certainly take the fantastic guitar riff, piano accents and chugging bass in the low end over the usual reverb-saturated, overly dark piano that accompanies this sort of tune.

Gary Allan Smoke Rings In The Dark


Bourbon Borderline

Smoke Rings In The Dark (1999)

Written by John Wiggins, Harley Allen, and Jennifer Bibeau

Sure, it’s a pretty standard theme for a country song – a reflection on what happened the night before, where Allan acts against his better judgment and lets old memories creep up on him – but it also shows how far Allan had come as a pure performer by this point in his career. His first two albums have their moments, but they also rang as generic ‘90s country that failed to separate him from the rest of the hat acts. With Smoke Rings In The Dark, the lusher, atmospheric, California-inspired production tendencies not only helped the performances stand out more, but the song selection was stronger and more distinct, as well. Plus, as evidenced here, Allan was developing a more unique voice to express his pain.

Gary Allan Used Heart For Sale


Her Man

Used Heart For Sale (1996)

Written by Kent Robbins

The hit that started it all – a Waylon Jennings cover that, admittedly, is a bit of an odd choice for a debut single, but also got the ball rolling in the best way possible. But there’s a strength to this single that wouldn’t quite develop further until later on – Allan himself. For as awkward as some of the lines here are, and for as much as we never actually understand how he’s going to do better at being “her man,” Allan’s performance does the bulk of the work. There’s a real regret to his delivery, as if he’s truly caught off-guard by how irresponsible some of his actions have been and shows real dedication to, at the very least, try acknowledging those faults and work to overcome them.

Gary Allan See If I Care


Drinkin’ Dark Whiskey

See If I Care (2003)

Written by Chris Stapleton and Mike Henderson

For Gary Allan, this is pretty much as upbeat as it gets – where a chugging, dark guitar intro leads to a night of drinking, and where Allan is ready to face whatever consequences will inevitably come his way. It’d be nearly nihilistic if not for the jumpy fiddle, Allan’s low growl, and personification of the whiskey bottle in his hand to make it “fun” in a twisted way. The SteelDrivers’ version may have Allan beat in terms of pure power, but there’s a seedier disposition to this I’ve always preferred.

Gary Allan Alright Guy


Man To Man

Alright Guy (2001)

Written by Jamie O’ Hara

I love this purely due to its framing – where Allan puts his significant other’s ex in his place, creating a two-pronged benefit: one, being that it shuts down this hothead’s streak of toxic masculinity and entitlement; two, being that it lifts the female character’s role, where these two characters aren’t so much arguing over who gets her so much as affirming that she’s moved on from this dude. Allan’s toughness always was defined by personal scars over machismo, and this is one of the best examples of that.

Gary Allan Alright Guy


What I’d Say

Alright Guy (2001)

Written by Robert Byrne and Will Robinson

With all due respect to the late Earl Thomas Conley, Gary Allan’s take on “What I’d Say” is the best one, trading in the polish that dated the original for a thicker smolder to the instrumentation, anchored by Allan’s blunt tone to suit the content. It’s a great song either way, of course, but this is one of many examples here of how Allan truly made a work his own.

Gary Allan Get Off On The Pain


We Fly By Night

Get Off On The Pain (2010)

Written by Gary Allan, Odie Blackmon, and Jamie O’ Hara

Truthfully, it feels strange noting this as my favorite song from the Get Off On The Pain album, if only because it’s one of few reprieves from the usual pain that colors Gary Allan’s best material. Here, the stress that comes with the mundanity of an ordinary day subsides by night, and the subtle break in Allan’s delivery on the hook really sells the transition for me. Well, that, and the mix balance, which places the chugging guitar toward the back and lets the piano sit at the forefront for a more delicate, languid touch. It’s a subtle detail, but one I’ve always admired.

Gary Allan Set You Free


It Ain’t The Whiskey

Set You Free (2013)

Written by Greg Barnhill, Jim Daddario, and Cole Deggs

To this day, I’m shocked this was released as a single in 2013 to mainstream country radio – a slow dirge of a track content to toil away in its whiskey-soaked misery. I’d have preferred it to, say, “That’s My Kind Of Night,” but country radio no longer really spoke to me by this point anyway. And the wonderful thing about this is that it goes as dark as you’d expect it go for Allan in its framing and setup, with a curdling, ominous organ to lead it all in. For any artist, it’d be too bleak to cut. For Allan, it’s still not even close to being his darkest moment on record.


Lovin’ You Against My Will

Smoke Rings In The Dark (1999)

Written by Jamie O’ Hara

This … is a forgotten cut in Allan’s discography. Really, I get it – it’s not cutting as deep as “Smoke Rings In The Dark” or carries the pure firepower of “Right Where I Need To Be.” But it’s an exercise in tension I’ve always loved anyway, from the murky guitar, swells of strings and hints of reverb to compliment not only the pedal steel, but also highlight the dark, endless cycle our featured character goes through as he tries to move on.

Gary Allan Used Heart For Sale


Wake Up Screaming

Used Heart For Sale (1996)

Written by Jim Lauderdale and John Leventhal

This cut hinted at Allan’s potential early on, even more than “Her Man.” I mean, a languid, bluesy arrangement that reveals a character spiraling out on control from an endless nightmare? It’s surprisingly dark for any artist, but it was only the beginning for Allan. It’s another cut, too, where the real tension is emblematic in Allan’s drawn-out performance, which rises to a slight howl on the hook and only grows bleaker with every passing line.

Gary Allan Alright Guy


What Would Willie Do

Alright Guy (2001)

Written by Bruce Robison

In a pure musical sense, I wouldn’t think of comparing Allan to Willie Nelson. Not because of any competitive notions, mind you – they’re just too different to directly compare. With that said, this tribute makes sense – two musical underdogs who succeeded in spite of not fitting in, with one underdog offering a warm, restrained tribute to the other. The conversational tone helps imbue this track with the right amount of humor and respect without going overboard, even if there’s a lazy weed reference throw in, as to be expected. In any sense, the song certainly offers some sound advice.

Gary Allan Alright Guy


Alright Guy

Alright Guy (2001)

Written by Todd Snider

If Smoke Rings In The Dark was Allan’s way of branding himself as an outsider through a sonic expansion, Alright Guy does so through its lyricism and storytelling. I just mentioned “What Would Willie Do,” which, silly as it is, is pretty heartwarming and fun. And then there’s the album title track, where Allan has to work extra hard to make that outsider status appealing and can’t understand what anyone would possibly have against him. Self-awareness is the key to any good humorous song, and as this one goes way too overboard to sell its character as unlikable, it’s a blast all the way through – especially with the rollicking tones to the instrumentation to keep it loose and not overly serious. It helps, of course, that both Allan and Todd Snider’s brand of humor is of a darker variety, and this isn’t even the best Snider song Allan ever recorded. More on that later, though.

Gary Allan See If I Care


Songs About Rain

See If I Care (2003)

Written by Pat McLaughlin and Liz Rose

Truthfully, I’d love to hear a radio station that plays all of the songs Allan tries to avoid here. Of course, part of the larger point here is that the onslaught of songs about rain is purely psychological. There’s nowhere else in town for Allan go to console his pain, so he turns to music and finds that it’s only making things worse. And though it’s usually lazy to randomly list titles in these songs about songs, it’s effective here in capturing how there’s no two songs about rain the same, and how there’s not one he’d like to hear right now. It’s a bit ironic for Allan to record it, but it’s bitterness that doesn’t come with an easy resolution and leaves only Allan to blame for presumably ending things the way he did.

Gary Allan Living Hard


Half Of My Mistakes

Living Hard (2007)

Written by Radney Foster and Bobby Houck

My mantra in one song – where Allan takes accountability for past transgressions and faces them head-on to find closure, realizing that half of those mistakes in his life also led to a lot of good elements in his life. It’s only by facing that darkness head-on, after all, that we find what we’re looking for, not through mindless escapism. It’s a life lesson sold through Allan’s rugged, lived-in, straitlaced expression, further bolstered by the interplay of the main guitar riff and the fiddle for an understated, moody groove. Given the timing of this release, too, it’s a quiet, personal anthem for Allan.

Gary Allan Set You Free


One More Time

Set You Free (2013)

Written by Gary Allan, Hillary Lindsey, and Matt Warren

As I’ve discussed already, Allan’s lived-in tone can elevate just about anything, including something as simple and earnest as this. Sure, it’s a reflection on mortality that’s fairly common for any artist of Allan’s stature and age – especially for one who did achieve a huge comeback moment for one last victory lap with “Every Storm (Runs Out Of Rain)” – but it feels grounded and honest. Of course, it helps to have a good bedrock to sell the message, and with the minor, liquid guitar tones anchoring the bulk of this, it does. But it’s Allan’s performance that grows more powerful as the chorus rolls on, especially as he grapples with whether or not having one more chance would actually fix anything.

Gary Allan Tough All Over


Tough All Over

Tough All Over (2005)

Written by Jim Lauderdale and Odie Blackmon

I’m not surprised it took this long to get to the Tough All Over cuts (spolier alert: they make up half of this top ten). And while I’ve only hinted and alluded to Allan’s personal struggles with these descriptions, it’s hard to dance around it with these cuts. Granted, the title track to this album doesn’t quite beg the fuller conversation yet, especially when it’s framed as pretty standard breakup track. But, as the opening track, it comes through like a firestorm, with the blast of harmonica weaving its way in and out. The bitterness that comes through in the lyrical content is elevated by Allan’s demeanor, albeit in a different way. It’s the track that, naturally, suggests everything isn’t all right, especially with that ending instrumental breakdown and its rapid-fire precision.

Gary Allan Tough All Over


I Just Got Back From Hell

Tough All Over (2005)

Written by Harley Allen and Gary Allan

It’s well-documented by now, though it’s worth mentioning that Allan’s Tough All Over album is shaped around the grief felt from his wife’s (Angela Herzberg) suicide, with this being the bluntest acknowledgment of the situation on the entire album. What says it better than “I’ve been made at everyone, including God and you”? Yet for as much as Allan’s career has been shaped by moody material in general, he’s never let it consume or define him, and he’s not going to let it win here, either. But it’s certainly the most difficult of battles to overcome, where Allan’s weary resignation suggests he’s going to need a break before learning how to live again, even he’ll emerge a different person regardless.

It’s more complex than that, though; more uncomfortable, too. Allan’s going to question his own implications in how he got to where he is, and though it’s hard to determine what exactly is going through any person’s mind at their lowest point, there’s still a heavy weight of guilt felt by everyone else involved in their daily lives for what they did or didn’t do. More than anything, it’s Allan’s starkest moment on record.



Long Year

Smoke Rings In The Dark Deluxe Edition (2019)

Written by Todd Snider

Sad as it is to say, I haven’t loved a new Gary Allan song since “It Ain’t The Whiskey.” It’s ironic, then, that the one exception to that rule is a song that largely got overlooked last year and was never a proper single – a bonus track for the 20th anniversary edition of the Smoke Rings In The Dark album that just so happens to be another Todd Snider cover. Yet for much as I do love “Alright Guy,” this is a better fit for Allan – a jangly, dobro-driven, intentionally off-beat, messy look at the alcoholism recovery process and the hazy feeling that comes with finding the courage to attend a meeting, especially with those who too don’t know if this is all for the better or not. And Allan is equally uncomfortable in his role with it all, questioning how much in common he could really have with that “12 step crowd” before finding himself back at the bar, painting a hopeless portrait of addiction that adds gravitas to the lyrical hook.

Gary Allan See If I Care


A Showman’s Life (w/ Willie Nelson)

See If I Care

Written by Jesse Winchester

“What would Willie do?” Why, he’d sing another duet with someone, that’s what. Yet for as lighthearted as that aforementioned song is, “A Showman’s Life” is a much different story, framed through the weary resignation that comes with being an artist even just a few years into the game, let alone for someone like Nelson who understood the message years ago. Sure, it’s a bit general – I’d argue it’s not even Allan’s best example of this sort of song – but no less true in hitting the mark of the disillusionment that comes with stardom, where you’re constantly surrounded by people – adoring fans, in some cases – but still feel like you’re slowly losing a part of yourself trying to approach the music-making process as a job, rather than a self-fulfilling activity.



Promise Broken

Tough All Over (2005)

Written by Deric Ruttan and Margaret Findley

What’s helped Tough All Over endure as one of the finest albums of the 21st century so far is its emotional complexity – the background speaks for itself, but it’s not solely centered around Allan’s journey to recovery, nor is that journey all that easy to follow. There’s slips and cracks where the darkness wins for a moment, and where Allan’s narrative is sometimes ours. Case in point, a personification of a broken promise that speaks to a scenario we’ve all found ourselves in, probably more than once, too. Time slips away, we overthink our roles in current and past scenarios and let even more time slip away, then, after a certain point, it doesn’t matter anyway. What’s done is done. It’s blunt, it’s uncomfortable, and it’s even judgmental, but in a way that doesn’t exclude anyone from the darker side of themselves.

Gary Allan Tough All Over


Putting My Misery On Display

Tough All Over (2005)

Written by Gary Allan

Here’s a mantra I don’t agree with: “write your own songs.” Not to undersell some of country music’s greatest writers, but I’ve always assessed music on multiple merits. A well-written song can have a boring presentation; a clumsy song can ring loudly with a powerful performance or arrangement behind it. And we can’t, of course, undersell the vocal performance. Some equate a criticism of vocals to pure power, but there’s more to it than that. A powerful singer can offer a boring rendition; not-so-great singers can hide their technical abilities with pure emotion. There’s no actual formula to what makes a song great or how it affects us, hence why it’s called art to begin with.

All of this is to say that Gary Allan didn’t write a lot of his best material, but he sang it like he did. To play devil’s advocate, though, there’s nothing better than hearing an artist’s interpretation of their own work, even if it isn’t necessarily the “best” version. “Putting My Misery On Display” is as uncomfortable as it is cathartic, then, finding Allan ripping away the veneer that comes with a showman’s life he sang about one album earlier with even sharper precision. To hear an artist talk about the touring and music-making process as a soul-sucking entity says all that needs to be said about Allan’s mindset during this time, where the drawn-out guitar outro has more life to it than Allan himself does. It’s honesty formed in a way we’d never hope to hear from our musical icons.

Gary Allan Smoke Rings In The Dark


Don’t Tell Mama

Smoke Rings In The Dark (1999)

Written by Buddy Brock, Kim Williams, and Jerry Laseter

There’s a few different versions of this song floating around, but Allan’s, to me, is the definitive one. And over twenty songs in, it’s hard not to resort to the same well of adjectives to describe why – Allan captures the needed shock to sell a tragic event he witnesses firsthand, and of every version out there, only he captures the sobering reality that comes with hearing a dying man’s final words, made all the more tragic by the tinge of regret surrounding those words. Not that it’s a necessary selling point for me – especially when I’ve always loved Allan’s modern balance of country and rock with a Californian touch – but this is the type of bleak story song that sounds best as a classic country ballad.

Gary Allan It Would Be You


No Judgment Day

It Would Be You (1997)

Written by Allen Shamblin

It’s Gary Allan, so, yeah, I’m a bit miffed this was only a hidden bonus track on his sophomore release, especially with how gutsy it is. But given how Allan’s career was just starting out and in limbo from some inconsistent single choices, I get it. At any rate, what a song – a stark acoustic ballad that tells of a robbery made worse by three malicious kids out for blood. It’d be a damning story on its own, but what pushes it further is the moral ambiguity – how, just for a moment, the narrator thinks of what could have led the kids to commit such a crime, touching on themes of abuse and neglect that shaped them and the situation. It’s not so much forgiveness as it is empathy, showing how bad actions only lead to more bad actions, and how that needed judgment day may never come at all, if it’s possible to judge anyway.



Best I Ever Had

Tough All Over (2005)

Written by Matt Scannell

I’ve touched upon a few excellent covers here already, but this one hits a bit differently. A take on a Vertical Horizon song that acted as Allan’s first piece of new music following the aforementioned unfortunate incident, it’s a particularly brutal piece to hear in that context. And then there’s the subtle line change before the last chorus to add a layer of complexity to the situation, only further amplified by the Tough All Over album itself, and showing how Allan is doing his best to just … understand. A fitting first step to overcoming grief, really. It should be obvious by now how much weight Allan’s delivery adds to a deceptively simple sentiment, but it bears repeating that, of all the songs here Allan “made his own,” this is the most obvious example.



Smoke Rings In The Dark

Smoke Rings In The Dark (1999)

Written by Rivers Rutherford and Houston Robert

This is the hit that forever changed Allan’s career, where he went from scoring the occasional top ten to being someone worth watching for the long haul. He mined his best artistic instincts on the eventual album, but it all began with its lead single title track. And there isn’t much not to love about this song: the sweeping, dreary atmospherics; the liquid strums of guitar or pedal lingering faintly to great degree; and Allan’s tired resignation that things are over between him and his significant other, letting the relationship run its natural course. It’s a track where Allan unearthed his potential to paint himself as the wandering loner – not an aimless drifter, but rather someone who’d need to follow his own path to find any vestige of peace or solace. And this, to me, is his best showcase of that. How ironic that a eulogy would breathe new life into his career.


  1. I love Gary Allan and Smoke Rings in the dark is my favorite over all. This is a good selection of his songs but I’d have included “Life Ain’t Always Beautiful”.

  2. I have Radney Foster’s take on “Half of My Mistakes”. It’s actually my most frequently played RF song in my i-tunes library. I just have GA’s GH album. A song not among your favorite 25 is “Tough Little Boys”. I like it a lot even though nobody would ever call me tough. strength still is my weakness)

  3. Great list. It was really nice to see “No Judgment Day” here, especially so high. If that’s not No. 1 on my list, it’d be pretty damned close. It’s my understanding the song was based on a true story, with a friend of writer Allen Shamblin’s father as the victim. Powerful, powerful stuff. Still makes the hair stand up on the back of my neck

    As odd as it may seem, given that the song could suit a lot of breakups, “Puttin’ Memories Away” was the one that got me from TAO. In the context of when it was recorded, it just came off as one of the saddest things I’ve ever heard.

    Just out of curiosity, did you ever hear Allan’s version of Chris Knight’s “Highway Junkie”?

    • @ the pistolero

      Well … I hadn’t heard it until you commented about it! Just checked it out – great stuff. Might have even made this list if I got to sit with it a bit longer. Thanks for bringing it to my attention (also noticed the soundtrack it stems from has some good stuff, so thanks for that, too!). It seemed like for a while Chris Knight’s tunes caught on with other artists – wish that was still a thing.

  4. Yup, it was that soundtrack — with that song, Knight’s own rendition of “The Hammer Goin’ Down,” and Jack Ingram’s “Drivin’ All Night Long” — that made me aware of the existence of the Texas music scene, or more accurately what I’ve seen referred to as Texas Music 2.0. Not many folks cover Knight’s songs and sound as good as he does, but Gary Allan’s way up on that list. (I also liked Lee Ann Womack’s “Send It On Down.”)

    Back on topic though, I was also a pretty big fan of “Alright Guy.” I actually heard that song a few times on the radio, on KIKK 95.7 out of Houston, TX back around late ’01 and early ’02. I ended up buying that album because of that song, albeit several years later.

    (Can’t lie, though, I like George Strait’s version of “A Showman’s Life” a lot better, mainly because of his vocal perfomance. I mean, Gary’s is good, but George’s is just transcendent for me, even if it would’ve been a lot better with Faith Hill’s harmony vocal turned down a bit from the second verse on.)

    Oh, and another fun fact about “No Judgment Day” — if my memory is correct, Gary Allan actually wrote a song for that album, but he believed in “No Judgment Day” so much that he put his own song off so it could be included on the album. I am really glad he did.

  5. Gary’s long been one of my favorites and the artist I’ve seen live more than any other. Hopefully his new song means a new album might finally be imminent.

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