Favorite Songs of 2021

This is always the hardest list to make, mostly because, unlike my reviews, where I aim to describe music on a technical level, this is always about setting emotional context behind my picks beyond a purely intellectual exercise. It’s one reason why I’ve decided to just adopt “favorites” in the headline over “best of,” but it’s also a statement I needed to make right out of the gate with 2021.

After all, this was a year that was personally very scattershot for me, where my high points resulted in more moments of euphoria and my low points … well, you get it. It also means that refining this list down to the usual top 50 was more exceedingly difficult than normal because of how varied it was … at least in terms of themes and sound. In terms of what was included, I’ll admit that there are likely less dark horse pick this time around; most of what you’ll see here will be reflected on my eventual favorite albums of the year list. Of course, it was also a year where my usual three song limit per artist was tested more than ever before, and where I seriously considered implementing a one song per artist rule. But that wouldn’t be quite reflective of my year, and given that I’ve always billed these as soundtracks set to a moment in time, hopefully you all understand that these are my picks and nothing more.

One more house rule, as per tradition: for a song to be eligible for this list, it had to be included within an album released this year that I covered. I’m not counting individual singles from my short-lived Boom-or-Bust Jukebox weekly series from earlier this year, though, just for the sake of consistency. Lastly, I tweeted out a few honorable mentions that barely missed the cut, just in case you’re looking for more songs.

Without further ado, let’s get started.

No. 50 – Mac Leaphart, “That Train” (from Music City Joke)

There’s songs where you can describe what you like about them on a technical level – in this case, the faster-paced rollick driven by the blasts of harmonica and rough acoustics, followed by several excellent bluegrass-inspired solos toward the end – and then there’s songs that hit on such a personal level, that it’s hard to say much beyond that. “That Train” described hitting burn out and frustration with one’s own path in life in the bluntest and most vulnerably relatable way I’ve likely heard since American Aquarium’s “Losing Side of Twenty-Five,” and that’s a high compliment. Oh, and it’s all sold by a lead singer who sounds haggard and fried enough to make it believable. It won’t be the only time we see Mac Leaphart on this list, but it is the one time where I don’t need to say much to articulate why this song is included here.

No. 49 – Brandi Carlile, “Broken Horses” (from In These Silent Days)

To be honest, I didn’t love Brandi Carlile’s return with In These Silent Days quite as much as I wanted to, but “Broken Horses” was the easy exception to that. Beyond being titled after her excellent memoir, it’s a testament to her spirit and vitality that, coupled with the fantastic snarl courtesy of that recurring electric guitar riff and anchored bass groove, is absolutely pulse-pounding in its ferocity. The real strength of this song, though? Carlile herself, who absolutely lets loose with legitimately anthemic firepower and never lets up once. I mean, I could maintain my professionalism and just keep going with the descriptors … or I could just say it kicks ass. It’s a foray into progressive rock I didn’t see coming from her and would definitely encourage on future projects. It just may be one of her best tracks to date.

No. 48 – Yola, “Diamond Studded Shoes” (from Stand For Myself)

I mean, there had to be at least one jam from Yola here, right? With the fantastic jump and rollicking punch carried by the electric groove that leads to one of her best-ever hooks, this certainly counts … but it’s also Yola speaking truth to power in her exasperation of the inequality present around her, unafraid to point the finger at those responsible and take proper action. And by framing it as a song for the people to fight and correct the systems in place, it’s got the populism and stomp needed to connect as a legitimate anthem. It’s the album centerpiece for Stand For Myself, and mighty worthy one, at that.

No. 47 – Amythyst Kiah, “Sleeping Queen” (from Wary + Strange)

This is one of a few songs on this list I’d best describe as “nightmare fuel,” and it’s the one where I’d almost mean that literally. It’s Amythyst Kiah sifting through fragments of a dream-like state against an equally murky, atmospheric backdrop of reverb and muddied tones that, coupled with her impressive howl throughout, is almost like an anxiety attack about a common lack of empathy seen in the world today, and Kiah’s own role in it – a world crashing down in the blink of an instant, just as worlds do in dreams. Unsettling, for sure, but that’s why it’s here, and it’s certainly a dream that won’t fade.

No. 46 – Alan Jackson, “The Boot” (from Where Have You Gone)

And just like that, Alan Jackson returned to deliver a track told with the benefit of a veteran’s poise, and in more ways than one. Here, he plays the role of an older man in a bar who offers advice to a younger person on love and relationships, all told through unfortunate experience on his part, where he just hopes his new friend doesn’t repeat the same mistakes he presumably did. Sure, it’s a common archetype and setting to frame a country song around, but Jackson infuses it with both storytelling wit and real stakes by framing it as an actual conversation, where the younger man tries to initially ignore the older man’s advice in favor of stubborn pride, adding a sense of realism to it. To put it another way, it’s a big reason why I’m glad Jackson made his return this year, because this only adds to the canon of his absolute best.

No. 45 – Chapel Hart, “I Will Follow” (from The Girls Are Back in Town)

I’ve told myself all year that “You Can Have Him Jolene” is the Chapel Hart song I liked most this year, but “I Will Follow” is the type of song that stuck with me more as the year progressed. Yes, it’s an inspirational track, but I think what I initially ignored about it is how truly inclusive it is, adding a sense of realism to its stakes. Ergo, it doesn’t matter who you are or what your skin color is, you can’t let others’ perceptions of you dictate your chosen path in life; you’ve just got to follow the beat of your own drum. And Chapel Hart did it even one better by framing it as an absolutely infectious anthem with a deliriously catchy chorus and hook, all backed by a well-balanced mix of handclaps, sunny tones, excellent harmonies, and a solid bass groove to add driving momentum to a track brimming with exuberance. Oh, and it’s also a good reminder that, if you’re not onboard with Chapel Hart yet, you’re missing out.

No. 44 – Jack Ingram, Miranda Lambert, and Jon Randall, “Breaking a Heart” (from The Marfa Tapes)

I know I crafted the list, but I’m a little surprised this is the track from The Marfa Tapes that ended up sticking with me most, especially when I’ve credited Miranda Lambert as the real star behind it all year. I mean, she still is here on this post-relationship song as she provides harmony to Jon Randall’s aching tone – no surprise that he’s one force behind “Whiskey Lullaby” – but it’s honestly that hook that really put things into perspective for me: “I don’t know if the hardest part is being heartbroken, or breaking a heart.” It shows empathy for the other partner and suggests that sometimes relationships just fall apart naturally, and the hardest ones to break are the ones where the guilt can’t really be assigned to any one party or factor. It’s complicated, and while this is more broadly sketched in comparison to other tracks in this vein and incredibly short, I heard the message loud and clear.

No. 43 – Jeremy Parsons, “Masquerade” (from Things to Come)

This went from being a lower track on Jeremy Parsons’ incredible comeback album to one of my absolute favorites on it. I initially dismissed Parsons’ examination of hypocrisy and the facades we front as a little too preachy and overblown for its own good, especially on an album where the plainspoken poetry is the greater asset. Only, it’s complicated, messy territory, so resorting to metaphors of the masks we wear in our efforts to appeal to others is understandable. Plus, Parsons is quick to point out that he’s just like everyone else he’s critiquing here; the irony isn’t lost on him. And in a year where I spent more time people-pleasing instead of taking off my own metaphorical mask and being myself … yeah, I needed this more than I initially thought.

No. 42 – Eric Church, “Hell of a View” (from Soul)

I’m not surprised this became one of my favorite hit songs of the year, but I am surprised this ended up being within my top favorites on Eric Church’s triple-album project from this year – especially when I’m breaking my own rule and including all three projects as one entity. Of course, I’ve already explained why I like this track so much elsewhere, so I’ll just say that this is a love story I can get behind and support. It may be on Soul instead of Heart, but it’s a track where Church wears his heart on his sleeve, and it’s a good look.

No. 41 – Charles Wesley Godwin, “Blood Feud” (from How the Mighty Fall)

So, this song is kind of nuts as a whole, and I’m surprised Charles Wesley Godwin even made it. I’m not surprised he pulled it off, mind you, but considering that this is a fight song where blood gets shed and everyone walks away with physical and emotional scars … or just doesn’t walk away at all, it’s an absolute frenzy from start to finish. Yes, I do wish Godwin himself was a little higher in the mix to accentuate his grizzly tone, but I also like the idea of having everything get lost within the shuffle of this turbo-tonk tune to better support the fact that this is just a brawl to behold in all of its bloody glory. Godwin isn’t screwing around here, and if I’m looking for another reason why this made the list, it’s that chilling end howl, where the fight has now ended, the family has been avenged, and the characters … well, they’ll now have new demons to wrestle with; I think I’ve said enough.

No. 40 – Carly Pearce and Ashley McBryde, “Never Wanted to Be That Girl” (from 29: Written in Stone)

Come on, Carly Pearce and Ashley McBryde team up for a perfectly balanced duet in which they find out they share the same significant other who’s been cheating on both of them … it was going to make the list on that alone, most likely. I like, though, that it’s framed within the context of Pearce’s divorce album, which focused just as much on Pearce’s own decisions and path in life as it did the scandal in question. Of course, that’s also the sad beauty of the track. Both women will blame themselves for letting something like this happen even though it’s neither one’s fault, and there’s an unfortunate reality sketched there that gives the song its heartbreaking resonance. Coupled with fantastically burnished production to let that heartache sizzle, it’s a song I’m surprised has taken off at radio given that entity’s chilly reception to both artists – but a hit I’m glad for, all the same.

No. 39 – Jesse Daniel, “Gray” (from Beyond These Walls)

This is a song many are rightfully praising as one of Jesse Daniel’s best, and I can easily see why. Framed as conversation between him and an addict friend who’s only further spiraling out of control with every passing day, what gives this track its resonance is its context. Daniel understands what his friend is going through, because he’s also been there. But he’s not going to let his friend assign blame to anyone or anything that doesn’t deserve it, and while finding help and taking that next step is more difficult than anyone outside of that circle could likely ever imagine, it doesn’t mean that Daniel is going to sit by idly and let it continue. And yet, it’s not an angry song. Against a faint acoustic accompaniment with only a slight swell of fiddle and strings later to lend further support, it’s sad, where despite his harsh message, Daniel wants to help and just doesn’t know the exact right step to take. More importantly, though, he doesn’t want to see a friend fade into gray, and that it ends on a bleak note with no real resolution is a little too frighteningly reflective of a common situation.

No. 38 – Triston Marez and Ronnie Dunn, “Where the Neon Lies” (from Triston Marez)

All year I’ve described this as the sibling song to Brooks and Dunn’s “Neon Moon” we didn’t know we needed, and while I could probably end it right there, there’s so much more to love about this song. No, it didn’t need to be a duet, but Triston Marez and Ronnie Dunn have such great chemistry and sound fantastic placed against rich, full tones and a mix of somber-sounding piano, pedal steel, glistening acoustics and a solidly anchored bass groove that ramps up to build one hell of a chorus and hook. It’s a tried-and-true country song that works within a familiar setting and goes all the way with it in concept and performance, and it’s the kind of song that, in a just world, would have been a multi-week No. 1 hit at radio this year.

No. 37 – Lainey Wilson, “Things A Man Oughta Know” (from Sayin’ What I’m Thinkin’)

Like with “Hell of a View” before it, I’ve already discussed this single for a certain other list of mine, so I’ll keep this brief. I wish more of Sayin’ What I’m Thinkin’ had been like this, but as a breakthrough single, it’s an absolutely deserved moment for Lainey Wilson. Fantastic stuff.

No. 36 – Mike and the Moonpies, “Hour on the Hour” (from One to Grow On)

Mike and the Moonpies returned to what they did best with a vengeance on One to Grow On, and one of its best moments is this sad-sack heartache track in which Mike Hermier is the star of the show – well, on top of that fantastic pedal steel and bass interplay, that is. But really, for such a well-worn, timeless concept, Hermier sells being haunted by a former love through a song he hears played every hour on the hour on the radio with one of his most passionate performances yet. He’s the kind of character you can’t help but feel sympathetic for, given that he keeps trying to move on and just can’t. Anyone who has heard this, though, knows why it’s here, and it’s because of that incredible crescendo on the bridge that continues to amaze me with every revisit. Ironically enough, it’s not the only Mike and the Moonpies song to rank among their best for that very reason, but … more on that later.

No. 35 – James McMurtry, “If It Don’t Bleed” (from The Horses and the Hounds)

There are multiple artists here where I struggled with which three of their songs to include, and that’s not something I can say about other years. So, while this could have easily been “Canola Fields” or “Decent Man” or the title track in this spot, “If It Don’t Bleed” is the James McMurtry song I chose to kick off his entries, and it doesn’t seem to be a surprisingly popular pick. I get it – it’s certainly not the grandiose statement one typically expects from him. That’s kind of the point, though. He’s at the age where mortality is weighing a little more heavily on his mind, and he’s simply content with living life as is and doesn’t see the need of seeking salvation through some grand plan. It’s a refreshing take on the topic that, despite being aimed at an older audience, could easily be applicable to anyone at any stage in their life, especially those who need to learn how to live and let live. Oh, and it’s also one of the most rollicking and catchiest songs McMurtry has ever recorded, letting that hard message hit just a little bit sweeter. I believe I blasted this at least once a day throughout August, and it’s a song even I needed this year.

No. 34 – Emily Scott Robinson, “If Trouble Comes a Lookin’” (from American Siren)

And now, another artist for which I struggled to decide which three songs to include! I’m also struggling to find a good entry point to describe this song, which frames an affair between a married woman and a priest as … oddly jubilant? The irony isn’t so lost within the context of the album itself – which challenges listeners to see the possible beauty in sin and shame – but here, there’s no bitterness or anger present, or even regret. There is beforehand, for sure, but afterwards, she finds the attention and devotion she longed for, and he realizes that there’s other ways to find God than just trying to lead a perfect life that won’t happen for anyone anyway. No, if anything, this song is almost playfully joyous in how this affair is actually a good thing, and that while there are still consequences involved, it isn’t so black and white as it appears; it’s about finding a new faith.

No. 33 – Mac Leaphart, “Ballad of Bob Yamaha or a Simple Plea in C Major”

So, this, simply put, is a song told from the perspective of a personified guitar that relays its journey of being handled from one bad musician to another, and it’s absolutely hilarious all the way through. I’ve compared it to Jamey Johnson’s “The Guitar Song” all year, but that song was all about the pure joys of music itself from a dramatically sincere viewpoint. This is too, but it’s much more frank in just how terrible that journey has been for this poor instrument, from endless repeats of Bob Seger and Taylor Swift songs to below and beyond. As for why it works, Mac Leaphart paints it with so much humorous sincerity, that one need not be a musician to have a riot with it. It’s purposefully played terribly and all the better for it, and when are you ever able to say that about a song? A song one needs to experience, rather than hear.

No. 32 – Sierra Ferrell, “Whispering Waltz” (from Long Time Coming)

From that opening minor mandolin chord accented by the dobro interplay, I was reminded of, say, Alison Krauss at her best. Of course, Sierra Ferrell is in a separate vocal class of her own, and while she’s always been noted for her power and tone, this is a song that tests her emotional range. “Whispering Waltz” finds her caught in the immediate aftermath of the revelation of her significant other’s cheating, when they whispers another partner’s name while in bed together. And even just working within that context, there’s so much added weight to that hook of “now you don’t have to whisper, I know,” confirming her deepest fears and finding out about it in one of the worst ways possible, all while she relays how much she still loves him and isn’t sure how to proceed. Haunting song, and a fantastic reason why it’s been a “long time coming” for Ferrell, indeed.

No. 31 – Mac Leaphart, “The Same Thing”

OK, one more Mac Leaphart track, and one I’ve always appreciated for the subtleties beneath it. Leaphart finds himself in a chance encounter with an old partner from afar, and while neither of them acknowledge one another publicly, he reflects that they’ve both moved on, and that that’s OK. For one, it’s revealed that his recklessness caused the riff between them in the first place, and he’s just happy she moved on and found the happiness she deserved, with a partner who won’t see the same thing in her that Leaphart did, but something that will still be just as valid. Surprisingly mature and well-framed all around, it’s a closing of the door and finding the next step to put forward that characterized what made Music City Joke great as a whole. And that it’s my favorite Mac Leaphart song of the year … well, that says a lot.

No. 30 – Scotty McCreery, “The Waiter” (from Same Truck)

I think Scotty McCreery is ready to join the ranks of, say, Jake Owen – he puts out albums I’d only best describe as halfway decent yet always has one or two songs on it that completely redeem it and his career as a whole. If that sounds harsh, it’s because while the word knew him for “You Time” this year, I knew him for this fantastic deep-cut gem. Sure, it plays to easy sentimentalities in sketching an old man who frequents the same restaurant he used to go to with his wife who’s now passed on. And by having him pretends she’s still there while everyone looks on, I get why some would find that overblown and corny … until you know someone in a similar situation, and know that this track’s framing isn’t really all that uncommon, especially when it’s played sincerely and McCreery is the type of mature, grounded vocalist to sell it well. I also like that he plays the role of a waiter empathetic toward the old man’s situation and that the old man himself is very much aware of what he’s doing. It’s just a heartbreaking country song that provided an easy bright spot in mainstream country song this year, and while I don’t predict it will be a single … man, it should be.

No. 29 – The Steel Woods, “Ole Pal” (from All of Your Stones)

Another song about loss and the aftermath of its effects on those left behind, and also one framed as a letter from a friend on Earth to another one departed as a result of war. Life moves on, of course, and while this friend makes sure his buddy’s loved ones are provided for and that everything he left behind back home will continue on in some form, you understand that no one’s there to make sure he’s OK, because he’s lost his best friend and still isn’t sure how to take that. It’s achingly sad and relatable in framing the real effects death can have on those left behind trying to cope, and in the aftermath of Jason “Rowdy” Cope’s passing … yeah, a little too real. Everyone else highlighted “Run On Ahead” as the best tribute to him, and while that just barely missed the cut here, this was the song that cut a little deeper for me.

No. 28 – Margo Cilker, “Broken Arm in Oregon” (from Pohoyllre)

This is a song squarely directed at a younger audience, but an audience full of listeners that feel much older than they actually are, which I think was a common feeling in 2021. I’m fairly certain even I and Cilker consider ourselves a part of it, too, because while much of Pohoyrlle was framed as her collection of snapshots and memories collected on the road as she found her sense of place in growing older, “Broken Arm in Oregon” is the moment that snaps it back into reality. And, it does it all in one verse toward the end. Not that our worries aren’t unfounded or don’t have merit, but here, when Cilker has a chance encounter with a sexual assault survivor who is on the road to recovery but will live the remainder of her days forever scarred … it puts things into perspective quickly of how some of us are on different paths entirely that may not seem so bad after all. Empathetic in the best way possible, it’s a good reminder why now is the time to jump onboard Cilker’s excellent debut album. 

No. 27 – Charles Wesley Godwin, “Gas Well”

I’ve seen some folks describe this song’s plot as akin to the movie Hell or High Water, and while I kind of have to agree, I’m not complaining, because that movie is awesome, as is this song. Moreover, Charles Wesley Godwin is the sort of detailed writer who can sketch cinematic scenes with ease, and with the dramatic stakes to anchor them, too. Pretty much the entirety of How the Mighty Fall teemed with grizzly desperation, and in those times came even more desperate measures from its characters. Like with “Blood Feud,” it’s a song where success in what’s accomplished doesn’t feel as good as it’s supposed to; it’s just something to do to survive. It also opens as a slow-burning blues-inspired saunter before bringing in marching percussion and a more distinct Appalachian-flavored palette – plus a perfectly timed blast of horns right when the deed is done – all before ending as it began, giving this song legitimate momentum and firepower behind its plot. It’s one of Godwin’s best, and a good reason why How the Mighty Fall was no sophomore slump.

No. 26 – Jeremy Parsons, “Lillian”

What I loved most about Jeremy Parsons’ excellent Things to Come was how plainspoken he could be in both his insightful and quirky moments, enough to where the quirky moments kind of were the insightful ones, and vice-versa. “Lillian” is the kind of song that can kind of go over one’s head until some of those lines click in place, especially when it’s a straightforward country-rock carried by a deceptively great groove. What it’s about, though, is a couple’s relationship, framed around the female partner who is free-spirited and initially presented as the antithesis to the male character … until he reveals in the final verse that he’s just as crazy as she is, and that if anything, she taught him how to drop his guard. It’s a love song that can feel surprisingly honest and vulnerable without overdoing it, painting both partners as equal parts to one another, all while being pretty damn humorous, to boot. I’m a little surprised it ended up being my favorite song on the album, but I’m also not surprised in the slightest, and that’s an OK contradiction with me, especially in spirit of the song in question. 

No. 25 – Eric Church, “Heart on Fire” (from Heart)

Ah, yes, the opening moment to Eric Church’s triple-album project that, no, I can’t say explores new territory for him, but is still awesome regardless. It’s rock-star wish fulfillment that blatantly references old icons and revels in them, all framed around a past teenage romance that, coupled with the bright, jaunty keys and propulsive groove, fits well within Church’s wheelhouse. But there’s no anger or resentment present, either – it’s just reveling in a memory and mining the best of it. There’s two other hidden strengths, though. One is Joanna Cotten’s backing contributions, and two is how the percussion ramps up for that “freedom of you dancing on the bow of your daddy’s old boat” line that really opens up this song. “Hell of a View” made the cut for both this list and my best hit songs of the year list, and this? This has an easy shot at next year’s list for the latter category.

No. 24 – John R. Miller, “Shenandoah Shakedown” (from Depreciated)

I admit, I was a half step away from loving John R. Miller’s Rounder Records debut, but “Shenandoah Shakedown” was the easy highlight off of it and a fantastic example of where could push his sound on future endeavors. In a broad sense, it’s a song in which Miller finds himself on the edge of goodbye with a partner due to old demons creeping back up again, but it’s a mind-warp as an actual song and in its allusions to what those demons are. From the minor, creaking swell driving it initially to when the percussion snakes in and that electric guitar smolders in the latter half, it’s easily the tensest moment on the album. And that’s on top of how Miller sets a scene with detailed and textured language, detailing his stormy, nearly dead relationship with his significant other in a haze while faced against the calm serenity of the Shenandoah river. It may not be a song with an easy resolution to it all, but when it’s as well-executed as this, I couldn’t care less anyway.

No. 23 – Carly Pearce, “29”

Carly Pearce’s “Greener Grass” just barely missed the cut for this list last year, and while I’ve always found her to be an underrated artist on her first two projects, 29 is absolutely the moment where she delivers career-best highlights. The title track was the centerpiece of the EP in February, and it was once again on the album in September, even beyond being a beautiful, well-balanced country song complete with rich fiddle and strings. It’s a song that showcases the duality of Pearce’s divorce and how it’s affected both her ability to love and the path in life she thought she had planned out. But, I like that “29” doesn’t so much toil away in its mire as much as it realizes that mistakes happen, and that they need not define a person. If anything, they can provide needed lessons learned that strengthen us and help us see things in a new light. There’s a fair amount of songs on this list that capture the hopelessness that comes with not being at the desired place one is at in life, but “29” is one moment that tries to pick up the pieces and figure out the next step. I didn’t go through a divorce this year, but I needed to hear this, all the same.

No. 22 – Cole Chaney, “Coalshooter” (from Mercy)

This is one of those songs where I just could describe the plot to justify its place on this list, which is damn-near southern-Gothic in its sorrowful outlook. Mercy as a whole stomped any romanticization of deep rural poverty into the ground through its harrowing narratives, and “Coalshooter” is the track that revealed the deeper realities of it. It’s all told through the words of a son trying to help his father escape the coal mining industry by taking his place on the job that speaks to the further paradoxical generational obligations that come with it. There are those that support staying as a duty or obligation to those that came before them, and others, like here, that support ripping away that veneer and breaking the chain, if able. Cinematic in scope and perfectly paced with the slow, creaking fiddle and banjo tones, it’s an early gem that continues to deliver. Believe it or not, too, it’s not even Mercy at its most brutal, but it may just be the album at its most visceral.

No. 21 – James McMurtry, “Blackberry Winter”

If there was a running theme to The Horses and the Hounds beyond simply growing older, it was in questioning one’s purpose in life once they reach a certain age. For some, that purpose never left, and if anything, it’s shifted toward new horizons, like on “If It Don’t Bleed” from before. But here, we have a mother who’s watched her kids grow up and move away and is now left to question what her own role is now. Like with “If It Don’t Bleed,” I like that McMurtry’s ultimate message conveyed to her is that living just to, you know, live is still a worthy pursuit, but is also empathetic to her – through an undefined outside role – and knows that living without a purpose can be terrifying to some people. It’s not so much about saving her as it is reassuring her that there’s still more to life out there, even as the song ends and she’s taken off without hearing that message. Perfectly framed with the right sense of lived-in maturity and empathy, it’s the dark horse candidate I absolutely loved off the album, and there’s one more equally dark candidate to come.

No. 20 – Allison Russell, “Persephone” (from Outside Child)

I think anyone who’s heard Allison Russell’s Outside Child would agree that “Persephone” is the album highlight, a pull away from the bleakness that otherwise defines it as Russell finds temporary escape from her abuser at a friend’s house … and learns what love can and should be. Even knowing that it’s all temporary and that she’ll have to return only to escape somewhere else again to find shelter and safety, it’s all portrayed as utterly joyous – right down to that well-executed clarinet solo – even though it shouldn’t have to be a rare occasion for her. It’s a song that turns a normal hookup into a needed respite that inspires a need to fight for what life could be, and shows what humans can be at their most empathetic, at that. Supported further by the warm, rattling rollick of the bass groove that’s further bolstered by the glistening pedal steel textures, it’s a song about growing up too hard and too fast, but also about having someone around to make it a little better.

No. 19 – Mike and the Moonpies, “Social Drinkers”

This may just be Mike and the Moonpies’ best song yet, an ode to drinking away one’s sorrows that acknowledges how Mike Hermier’s character is both part of the cliché and part of what makes its atmosphere a timeless indulgence. It’s a place where he can act as an observer and see that others are battling their own demons in their own respective manners, and that there’s comfort in knowing he’s got company to commiserate with. But, given that it’s still an isolated picture – all punctuated by minor, liquid groove anchored by the phenomenal pedal steel and bass interplay as well as echoes of reverb off the guitar tones – it’s still very much his downward spiral to sketch. Like with “Hour on the Hour,” too, this rises even higher thanks to that phenomenal bridge – and with an added key change, to boot. The band may have made a tribute album to Gary Stewart last year, but with “Social Drinkers,” they made something that could easily have fit within his catalog … but is also quintessentially theirs to command.

No. 18 – The Steel Woods, “You’re Cold”

This entry will require some context, mostly because it’s part of an ongoing narrative that the band has told through separate songs on all of their projects thus far, a love triangle told from every perspective, and one where the last two pieces of it came on their latest album (for now, maybe?) This is the better song, in my opinion, not only for the references made that work without being overly self-indulgent, but because it’s a gruesome, epic, dark, southern-Gothic murder ballad that most certainly acts as the climax of that aforementioned story, if anything. To add further context, a male character, Jimmy, wants to run away with a lover, Anna Lee, but first has to break things off with his current partner, Della Jane, who responds to the news in both “Della Jane’s Heart” off the first album, and here, where the revenge murder takes place and is defiantly epic all around, right down to that extended, smoldering solo. It’s southern-rock rage with the potency and firepower to kick everything into high gear from the first note, and while that aforementioned context is important in understanding what’s going on, it’s pretty awesome in its own right, as well.

No. 17 – Eric Church, “Crazyland”

How fitting that, on a triple-album project that some would argue is divided against itself, Eric Church delivers an album highlight as equally scattershot and quirky. Of course, that’s the easy benefit to the writing here, where Church sketches an imaginary bar scene taking place in his mind, and addresses those multiple personalities that frame the album musically and through the simple aftermath of a breakup. Creative in its approach and well-balanced in its execution, it stands as a good reason why Church has always been a good storyteller, and that sometimes all this rock star needs behind him is warm acoustics, tempered percussion, and hints of banjo to pull it off. It’s among his best, and another good reason why maybe y’all should give the entirety of Heart & Soul another chance, if you can hear it all.

No. 16 – Emily Scott Robinson, “Hometown Hero”

This is a song where I predicted to know everything that was coming at me – the story of the veteran returning home from war that suffers from PTSD and succumbs to a downward spiral; a familiar country music archetype that nevertheless provides a needed perspective behind the best writers. And, since Emily Scott Robinson is an excellent writer, she manages to gut expectations by delivering one line that completely retools it to grant empathy to anyone suffering from some sort of depression: “Your kids are gonna grow up asking about you / How you could love someone and leave them and how both things could be true?” It’s quite possibly the greatest examination of that theme I’ve heard in country music encapsulated in a line that still devastates me with every listen, pushing past the ultimate sin of suicide and forcing listeners to understand not only the perspectives of those left behind to wonder why, but also the one of the person who was pushed to that limit. On an album where sin and salvation are often intertwined with one another, this is the moment where no one wins, but also sees why such a drastic step may have needed to be taken. It’s another testament to Robinson’s ability to mine nuance from complicated framing, and it won’t be the last one on this list.

No. 15 – Adeem the Artist, “Reclaim My Name” (from Cast Iron Pansexual)

Yes, the Toby Keith song came close to making this list, but this is the moment on Adeem the Artist’s Cast Iron Pansexual I wish had received even more attention this year, a closing of a book (and, given that it’s the closing track, album) that’s tinged with both regret and optimism for what’s ahead, all framed around a makeshift time machine they wish they could build for themselves. In order to do that, though, they need to sift through painful past memories and try to reclaim every taunt and hurtful word hurled at them, even from friends and family alike, and they need to do it by going back in time and convincing that child that who they are is worthy of love after all. Only, no one can actually build that machine, and as what sounds like a ramshackle device whirs loudly by the end before abruptly fading away and letting the acoustics carry the song out instead, you realize that the entire point is not to fix what can’t be fixed – it’s to be who you are now, own it, and realize that that can be more than enough to the right people. What this track accomplishes through its content and production is nothing short of astounding, and though we’d all like to build that machine for ourselves, there’s comfort in knowing that no struggle has to define us today … or tomorrow.

No. 14 – Morgan Wade, “Wilder Days” (from Reckless)

Oh, please let this take off at country radio. They could, after all, use some more women over there. Still, even if Reckless somewhat faded for me as a whole as the year progressed, this opening track was the easy highlight. Now, the easy answer as to why is: that hook – and also just the generally atmospheric, rollicking high that encapsulates its free-spirited energy from beginning to end. Digging a little deeper, though, a lot of Reckless as a whole had to do with learning from a troubled past and finding how to look beyond it and move forward while still learning more about ourselves along the way. What I appreciate most here is a sense of mature framing, namely in how she looks to her partner as a kindred spirit who understands that past on a somewhat even level. So, even when that partner acts guarded about their own past in fear of the memories it could reopen, she wants to know anyway, because for her, acceptance of that past and one’s self is crucial in learning how to forgive and move on. Refreshingly open-minded and adventurous, it’s a deserved breakout that paves the way for more “wilder days” to come, and I can’t wait. 

No. 13 – Pony Bradshaw, “Hillbilly Possessed” (from Calico Jim)

Trying to decode a Pony Bradshaw song almost feels like an exercise in futility, mostly because I’ve given Calico Jim a ton of listens over the year and am still finding out new things to say about it with every listen. I admit, “Hillbilly Possessed” is a song I somewhat misconstrued in my initial review as a potential criticism of snake-handlers and the culture surrounding it. But, like with the album as a whole, it’s more about forcing listeners to see Bradshaw’s distinctly rural characters as people and see them beyond the stereotypes associated with them throughout history. And as such … well, this song is still something of a mindwarp to take in, and I admit my basic love for it boils down to its minor, moody sway that leads to something even more sinister during that excellent crescendo toward the end. And, while I feel as if I should more add to that as we near the top ten, sometimes a song just needs to be experienced and understood to get it. There’s something oddly magnetic and hypnotic about this song’s allure I can’t quite articulate, but loved all year nonetheless. 

No. 12 – James McMurtry, “Jackie”

Heh, go figure – my favorite song on James McMurtry’s most lighthearted and accessible album to date is arguably its heaviest, bleakest moment. I mean, it’s not all heavy. There’s some quiet strings to accentuate its romantic sentiments – if one can call them that – plus, and this is something I didn’t catch in my initial review of the album it stems from, sleigh bells, of all things, to add a delicate touch for a life on the edge. McMurtry’s characters may be older on The Horses and the Hounds, but they’re not without their adventures or last hurrahs. So with that, we have the titular character involved in a fling with a long-haul trucker, all framed by Jackie’s struggle to get by all her life. And she isn’t about to expect a faithful relationship at this point in her life either. It’s all goes by as is … until she dies in a tragic accident. It’s got the same painstakingly heartbreaking and lived-in details to a McMurtry story you’d expect, and I’m not sure I’ve ever emphasized with a character of his living this much on the perpetual edges of exhaustion since “Rachel’s Song,” which is one of my favorite songs from him in general. And considering that’s a mid-’90s deep-cut, it’s all the more evidence that McMurtry hasn’t faltered a bit at this stage of his career. If anything, he keeps getting better.

No. 11 – Pony Bradshaw, “Calico Jim”

And … we’re back to Pony Bradshaw, most notably with his best song to date, a song that opens one of the most complex and beautifully layered albums of the year. And yet, I’d argue “Calico Jim” works well even outside of that context. Like with all of his material, the devil’s in the fine details, from the accented strumming that opens the song that carries a punchy, folksy rollick in its step, to the galloping percussion that evolves into an even faster-paced stomper complete with pedal steel by the final third. It’s damn-near anthemic at its core, but like with “Hillbilly Possessed,” it’s a tough song to discuss in regards to the actual content outside of the album context, another story song where we’re introduced to distinctly rural characters that Bradshaw forces us to see as people rather than through stereotypes. So, then, we have our titular character, who distrusts both sides of the political divide and just wants to be left to his own musings and appreciate the land around him, which he could if the corporations would stop trying to gentrify his land – and where that aforementioned anthemic core is as much for him as it is for any of us. Heady stuff, but like with the best of Bradshaw, it’s always worth the deeper listen.

No. 10 – Alan Jackson, “The Older I Get”

Yes, I’m aware that this first debuted in 2017; I have my house rules for a reason – it counts. Besides, it’s one of Alan Jackson’s best songs to date. I do wish that this song’s conventional wisdom dominated his last album over, say, “Where Have You Gone” or “Back,” but if you wanted evidence of another legend who still has it, look no further. I think what surprises me most is that Jackson didn’t write “The Older I Get,” but it easily sounds like he could have – a reflection on mortality that, while thematically familiar to other songs in his discography, is delivered with so much warmth, grace, and sincerity, that it’s just another winner among many for him. What elevates it further is the framing, namely in how Jackson doesn’t recall his past with regret, but rather looks ahead to what’s next. Not that he hasn’t carried his own burdens – he’s just not content to dwell on them, and it’s an exercise in honesty and humility that’s always characterized his best work. This is just his latest example.

No. 9 – The Divorcees, “Drop of Blood” (from Drop of Blood)

This was the first song of the year I loved deeply, but it’s also a tricky one to discuss, mostly because it’s a road song meant squarely for artists – the disenfranchised ones that openly question their path and choices made. I’d honestly place it among the ranks of, say, Lacy J. Dalton’s “16th Avenue” or Caitlyn Smith’s “This Town is Killing Me.” Only, this isn’t about Nashville, and there’s no bright side, either – just pure bleakness as our character openly ponders his work’s worth when it’s taken too much of his time away to build a family or spend time with loved ones in general, especially when no one’s listening to the songs anyway. Plus, “The stories that we told were of lives we never knew” may go down as one of my favorite lines about the songwriting process … pretty much of all time. It’s a frighteningly real examination of what this line of work can do to a person and how it can break their psyche down to nothing, inspiring great art along the way, for sure, but at what cost? And that it’s carried by a lead singer who excellently conveys that frustration and exhaustion while riding an excellently well-balanced minor melodic groove all the way down … well, if the question is whether or not anyone cared, The Divorcees at least one person in their corner.

No. 8 – Cole Chaney, “The Flood”

If “Coalshooter” tried to answer what the fight was worth in trying to make it in rural America, “The Flood”  rips away the veneer even further to reveal something devastatingly haunting. It’s another song in Cole Chaney’s discography with a bone-deep connection to its roots and an obligation to uphold familial obligations and history, but there’s something much more raw here in holding on as best as one can and having it not be enough in the face of a natural disaster – where losing everything means losing that history, too. It’s also where the weight of that responsibility can push people to the extremes. It’s what makes the direct honesty of Mercy so refreshing as a whole, but it also means that “The Flood” is a song I’ve found too tough to revisit at points this year. It’s bleak, it’s unflinching, and it ends exactly like you think it would. And yet, from the spare acoustics to the way Chaney delivers the line “won’t you spare this land I broke my heart and backbone for” with just the slightest quiver, knowing it’s for naught … yeah, it’s hard to believe this is a song featured on a debut effort. It’s a work of beauty in so many ways.

No. 7 – SUNDAYS, “Weightless Feathers” (from Inner Coasts)

There always seems to be an indie-folk album or song that I wrangle into conversations like these due to a very loose connection to country music (or because it’s damn awesome), and this year, that was through SUNDAYS and one of their best songs to date behind “Shade of the Pines,” “Weightless Feathers.” It’s one of those songs where its crystal-clear, atmospherically transcendent beauty trumps everything else I love about it, and while that’s not an uncommon descriptor for this band’s songs, I do like that it’s a song about confronting a past relationship both characters thought would work out, only for them to drift apart. Even still, there’s an admittance of how the experience shaped them and was, ultimately, an experience both partners cherish. But if I’m looking for the real nugget of beauty that pushed this over the top for me, it’s that magnetic harmony between singers Marie Linander Henriksen and Magnus Jacobson that, no, may not push this into true duet territory, but is an added touch I’ve appreciated with every listen.

No. 6 – Lucero, “Coffin Nails” (from When You Found Me)

If there’s a common theme to this top ten, it’s that it features career-best efforts from artists years or decade into the game, and while fans were divided on Lucero’s Where You Found Me from earlier this year, I think many could at least agree that “Coffin Nails” is among their best. For one, it’s the one song on the album that actually sounds like a Lucero song, with well-balanced, gorgeously mixed piano tones and stabs of bass that capture the song’s creaking, weathered edges. It’s a track with the breathing room to let its nightmare settle, which seems to speak to characters here with a familial history of wartime service that carries the same kind of different nightmares for every member that eventually returns home. It’s purposefully crafted by metaphors, but everything that needs to be said is, and even despite it, its resonance is as real as anything else. And the fact that it can make a familiar theme shine by adding a deeper level of haunting anguish to it, it’s why I stuck up for the album way back when, and it’s why I’ll continue to. I repeat, one of their best.

No. 5 – Emily Scott Robinson, “Let ‘Em Burn”

Many fans have cited this as Emily Scott Robinson’s best song to date, and I’d have to agree – almost without question. Again, to repeat what I about American Siren in regards to “If Trouble Comes a Lookin’,” the album this stems from is a constant battle and test of one’s faith, forcing its characters to question everything they knew about they life they’ve lived thus far and the rules they’ve followed. And while “If Trouble Comes a Lookin’” found a happy ending through an affair, with “Let ‘Em Burn,” that release is still there … albeit with much greater stakes behind it. It’s a spare piano ballad where the production magnifies it to become a beautifully transcendent and sweeping anthem – if only for the character in question – from the perspective of a married woman who sees her life and religion as increasingly empty and meaningless. She’s followed every rule and has set the good example for her own daughter, but she’s also reached a breaking point – and I like that the ultimate meaning could be possibly twofold, in that it’s something of a divine revelation in its own right that could allow her to become reborn and live a life she actually deserves … or that it could also act as a cry for help in stepping out into the great unknown, where letting everything burn away isn’t as metaphorical. I was initially inclined to believe the latter interpretation, but then I let a line like “what if desire is a gift and not a sin?” really sink in and allow me to see the hope she’s trying to muster for herself. Either way, it’s another entry here where its pure beauty and magnitude is beyond me to properly contextualize, but it certainly burns just as bright as the best songs here.

No. 4 – Flatland Cavalry, “Off Broadway” (from Welcome to Countryland)

Let’s take a brief break from ballads now by discussing Flatland Cavalry’s best song to date, a tribute to a St. Louis music venue frequented by Red Dirt bands that frames itself as a joyful bar sing-a-long and delivers on it, especially with its fantastic progression complete with an ending that never fails to brighten my day. And, of course, the writing delivers as well, as Cleto Cordero notes how even though time has shifted the landscape and changed him as well, he can return to that place with friends at any point and recapture the same magic of yesterday. It’s universal nostalgia of the best variety that’s so infectious and likable, and I like that it’s framed as both a tribute to making it and falling back in love with where you started. And between the gentle, wistful sway echoed by the accordion and fiddle alongside that huge hook, I continuously fell back in love with this song over and over again all year, and it’s easily the spark of joy I needed in an otherwise bleak year.

No. 3 – Joshua Ray Walker, “Flash Paper” (from See You Next Time)

These next three entries are incredibly difficult to discuss, mostly because they deal with similar, uncomfortable subject matter that, from the moment I heard them, were immediate locks for my top favorite songs of the year. Starting with the first one, I’m not sure if it’s atonement for not placing “Voices” on my list last year or what, but Joshua Ray Walker’s “Flash Paper” absolutely cut to the bone from the second I heard it. It’s framed as a difficult goodbye between him and his dying father, where Walker wishes for one last show of affection from a man who can’t afford to be that vulnerable … even in a moment that calls for it. The goodbye will have to come in what’s left behind rather than what’s said, which will, ultimately, stick more, like it or not. The thing is, when you’re like me and know someone who hung on to that sort of stubborn pride right down to the very end, you understand the weight of what a few last words can mean, both then and afterward. Now, the common critique for this song is that the buzzy electric guitar lingering in the low-end distracts from the content, but for me it was a good reminder of the distance between two people who can look at a situation so differently, yet say the same thing in their own ways. And in a way, I’m glad Walker was vulnerable enough to share this with us.

No. 2 – Jason Eady, “French Summer Sun” (from To the Passage of Time)

In a career that carries songs like “Barabbas,” “Daylight & Dark,” and “40 Years,” among so many others, “French Summer Sun” just may be Jason Eady’s finest work to date. And it gets there through little more than buzzy acoustics, Eady’s conversational, lived-in tone, and spoken-word poetry that earns comparisons to the late Tom T. Hall. Suffice it to say, this is a song where the writing takes the spotlight and everything else forces you to hang on to every word. It’s a war-time story that follows a soldier who miraculously avoids death in battle, returns home to start a family, and watches his family continue to grow with a grandson – a character Eady plays here. And, rather than glorify a familial obligation to service, Eady’s character finds his own way and makes it as a teacher, contributing to the world in a different – but no less valid – way. And then – spoiler alert – it’s revealed that the solider actually didn’t escape death, and that all of those characters and lives that Eady humanized never actually lived or happened, ripping away the veneer of the harsher consequences behind war. It’s a gripping reminder of how death will always take more than just one life, and that Eady lends each character their own parts to play within the story without regard to keeping things short for the sake of time is what drives the ending truly home. It’s pleasantly warm if you don’t know what’s ahead, but with repeated listens … well, it’s still beautiful, mostly because Eady crafts his own world in just a little over five minutes, but also allows us to live in it for a while by giving voices to real victims who won’t get to share a story themselves. It’s yet another reason why Eady is in his own class as a writer.

No. 1 – Amythyst Kiah, “Wild Turkey”

There’s a rare type of song that transcends one’s critical faculties, and it’s the kind that both hits closer to home than you’re comfortable sharing and, oddly enough, adds a level of comfort simply by its existence. It’s surprisingly easy to revisit, because it aims to address any lingering demons or trauma head-on, however uncomfortable it may be; what comes afterward is the real reward. Simply put, there are artists that can empathize with our plights, and all they usually ask in return is that we do the same for them.

What I’m trying to say is, Amythyst Kiah’s “Wild Turkey” filled that void for me in 2021 like no other, a song where she revisits her mother’s tragic death through alcoholism that occurred when Kiah was 17 years old, which she couldn’t process then nearly as clearly. It’s a song where the scars settled then, but didn’t quite manifest until years after the fact. It’s a search for forgiveness and empathy where said search may not be able to reverse the damage done, but can at least help to provide some vestige of closure. It’s harrowing, it’s difficult, and it’s delivered with a sobering directness, because Kiah is aware of just how long she’s walled herself off from the pain and knows she needs to face the past head-on if she wants to feel human again, and that adds a devastatingly relatable subtext for anyone trying to cope with a similar level of pain. And even if peace comes … it won’t erase those scars, but it will be the first step in healing them. Oh, and like with Wary + Strange as a whole, it’s a song where that examination of one’s own head space is reflected as much in the production as it is in the content. So here, we have empty, negative space intentionally used to support that feeling of sifting through the past, where the soft-plucked acoustics, wisps of mellotron, and low-end atmospheric elements help establish a harrowing picture for this song in particular, but allows for a fuller buildup later on that feels well-earned and supportive without hampering the mood. It’s a catharsis meant solely for Kiah, and I hope it at least led to some level of inner peace for her. But in 2021, it was a catharsis that transcended itself, and for me, unarguably the best song of a year that required personal reflection and a closing of the door on old demons. Here’s to hoping to feeling right again for 2022.

One thought on “Favorite Songs of 2021

  1. Wow, Zack, exemplary stuff. I applaud how much effort you put into this post every year, and how thorough and insightful your analyses are!

    I’ve heard most of these songs, and some I heard once but truthfully haven’t yet spent enough time with to be comfortable offering an opinion on, but for now I’ll comment on a few:

    -“29” hit a little close too home for me. It’s around that age when a lot of us really begin to realize that we’re not going to be young forever, and grow far more cognizant of time passing and self-conscious about how we’re spending it. Frankly, it sucks. Song’s amazing, though.

    -“French Summer Sun” is a songwriting clinic and a stunning illustration of how one event can have profound ripple effects throughout history and other people’s lives. It reminded me of the short story ‘A Sound of Thunder’ by Ray Bradbury. An incredible song that sadly probably not enough people have heard.

    -I certainly appreciated “Wild Turkey” while listening to the album, but I confess I didn’t know the full background or context behind the lyrics, and I didn’t quite grasp it all. Revisiting it with your thoughts fresh in my mind, I’m completely blown away. “Wild turkey in the car seat, the bottle’s empty, hope it gave her some relief” – damn, don’t think I’ve ever heard anything more devastating. That final stretch beginning at about 3:10 when the production gets more electronic-y (probably a poor way of describing it) and the intensity of her vocal increases – a 10/10 moment. This is a flat-out brilliant song. I’m obviously not as up to date as you, but from what I’ve heard, this would be a strong contender for my #1 as well!

    I’m planning on listening to more of your selections, and will post more reactions! Again, great stuff.

    Liked by 2 people

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