The Best Singles of 2020, Part Two: #20-#1

Best of 2020

Albums: Part One | Part Two

Singles: Part One | Part Two

Here are the twenty best singles of 2020, as voted on by staff writers Kevin John Coyne, Jonathan Keefe, and Zack Kephart, with ties broken by CU alum Dan Milliken.

The Best Singles of 2020, Part Two: #20-#1


“Sleep at Night”

The Chicks 

Natalie’s got receipts, and she’s not afraid to use them.  But what keeps “Sleep at Night” from being just a score settling record is the willingness to show that the pain caused by the betrayal is still there, and it’s not just felt by the wronged wife.  The kids got hurt, too. – Kevin John Coyne



“Mama Drank”

Jessi Alexander

In the hands of a less skilled songwriter, “Mama Drank” could’ve turned into a glib take on “functioning alcoholism,” but Jessi Alexander leans hard into the specifics of the day-to-day drudgery and unbalanced expectations that might lead a working mother to reach for a glass in the evening. The key here is that her narrator, despite working a full-time job, is also expected to be fully responsible for keeping her household running smoothly. Alexander’s bluesy delivery suggests she knows that “having it all” is the most loaded of prospects, and she makes no apologies for wanting a stiff drink to take the edge off. In fact, she turns it into an act of solidarity across generations. – Jonathan Keefe



“Six Years Come September”

American Aquarium

What’s always marked American Aquarium lead singer BJ Barham’s writing perspective is his lived-in detail and examination of his past, and an empathy for characters similar to, but not directly representative of, him. Like this one, who lost it all to alcoholism and a drunk-driving incident, and is trying his best now to just … survive.

It never seeks to draw sympathy or empathy from the listener, but rather to focus on the permanent guilt and consequences that will forever shape and destroy him, and hopefully dissuade someone from making the same mistake. Which, in an indirect sense, manages to draw that empathy from the listener anyway.

A tough song to listen to, even without any relatability surrounding it, and between the subtle touches of keys and reverb to echo that ghostly swell that pick up intensity toward the end, it’s one of Barham’s absolute best. – Zackary Kephart



“Under the Devil’s Knee”

Tré Burt featuring Leyla McCalla, Allison Russell, and Sunny War

It’d be unfair to say any one song encapsulated the gamut of emotions that ran through 2020; that’s just impossible. Here’s one that tackles the past and present, though, from the senseless murders of George Floyd and Breonna Taylor this year, to Eric Garner’s murder several years earlier, to the other victims we can’t afford to forget – all while centering on the racist core that fueled these senseless tragedies – not just this year or several years ago, but centuries ago.

It never forgets to humanize everyone mentioned here, naturally drawing its empathetic viewpoint, but also reminding listeners that progress isn’t made without action, and it’s a fight no one is immune from; certainly not at this point. Listen, then act; it’s the only way. – ZK



“Honky Tonk Hell”

Gabe Lee

Sometimes a song just sounds like a hit; with its crisp production and massive hooks, Gabe Lee’s “Honky Tonk Hell” is one of the year’s catchiest country singles that radio, of course, didn’t actually play. Granted, taking a shot at, “all the folks down in Nashville/Writing phony-ass country songs,” probably isn’t the best way for Lee to try to endear himself to the powers-that-be, but songs like this one prove that he more than has the chops to back up that bit of braggadocio. – JK



“Long Violent History”

Tyler Childers

Reflecting on a summer of protests sparked by racial injustice and police brutality, Tyler Childers dropped a surprise album of traditional fiddle tunes that he capped off with, “Long Violent History,” a stunning paean to empathy and dismantling of privilege. The way Childers drawls the word “conjecturing” is, in and of itself, a thesis on why authentic accents bear a hefty social currency. It’s all the more significant that he drops it into a line of just jaw-dropping self-awareness: “Now what would you get if you heard my opinion / Conjecturing on matters that I ain’t never dreamed / In all my born days as a white boy from Hickman / Based on the way that the world’s been to me.”

Childers knows exactly what he’s doing on every note of this track, from the opening bars that he lifts from “My Old Kentucky Home” to a plea to members of his own growing audience to consider how quickly they’d reach for their “papaw’s old pistol” if their neighbors who looked like them were dealt the same hands as George Floyd and Breonna Taylor. – JK



“The Problem”

Amanda Shires featuring Jason Isbell

“The Problem” cuts through all of the political posturing and warped moralization surrounding abortion and reduces it to the simple truth of a woman making a choice and her partner supporting that choice.   A testament to the power of unconditional love and a reminder for everyone else to mind their own damn business. – KJC




Jason Isbell & the 400 Unit

Jason Isbell’s songwriting opens windows that peer into forgotten souls.  “Dreamsicle” centers the experience of a teenage boy moving from town to town and navigating the broken relationship of the parents that he loves.  You never get the sense that he blames them for how their choices have impacted his life, but his look ahead to eventual reconciliation many years down the road reveals his intention to learn from their mistakes. – KJC



“Under the Sun”

Ruston Kelly

I can see the easy criticism that this – it’s just a broadly written inspirational track. Yet I’m then reminded that it’s Ruston Kelly behind the microphone, the dying star who found love and stability and now tries desperately to hang on to it. Much of Shape & Destroy explored that, really, even as old vices crept back in and forced Kelly to question everything he’d fought for up to that point.

But there’s a strength and reward in the fight itself, and hearing him belt out that final chorus reads more as a desperate promise to himself to keep going, even when it seems like he can’t. A frighteningly real and relatable sentiment for this year, and a song one can’t possibly discuss or love without questioning something about themselves along the way.  – ZK



“Looking For a Feeling”

Pam Tillis

Pam’s first solo single in thirteen years was worth the wait.  “Looking For a Feeling” has a pulsating groove that runs on a parallel track with the restless spirits captured in this song.  Tillis shows a deep understanding of their yearning and presents them with clarity and without judgment, a reflection of her unique gift a songwriter.  Like all of her great compositions over the years, from “Melancholy Child” and “Homeward Looking Angel” to “Life Has Sure Changed Us Around” and “The Hard Way,” “Looking For a Feeling” captures the fragility of the human experience through keen observation and with deep empathy. – KJC




Sierra Hull

It’s amazing how certain songs took on a new life this year, intentional or not. “Escape,” for all intents and purposes, is just a complex, sorrowful spiral that acts as a painful interlude on an album about the personal anxieties that come with growing up. Yet its core sentiment of feeling lost along that path was the one that gripped me most, personally, this year.

It’s unlike anything Hull has done yet, either, where that baritone electric mandolin is the perfect addition to capture the moody, rhythmic sway that just oozes uneasy tension. Captivating in its progression and equally as perfect, yet muted in a way that supports the content, where the echoed vocal pickups highlight the questions and anxieties running through Hull’s mind and works for anyone who felt more than a little lost this year. – ZK



The Chicks

From the electric shock of those three part harmonies to the cutting lyrics that slice to the bone, “Gaslighter” is a powerful showcase for the songwriting prowess and peerless musicianship of the Chicks.  “Gaslighter” is about an emotionally abusive marriage, but the message applies just as well to the gaslighting that so many of us have been subjected to over the last few years.  So many fires started by those who can’t take themselves on a road little higher. – KJC



“I Remember Everything”

John Prine

As John Prine’s final recording, “I Remember Everything” is an overwhelmingly emotional song that, ironically enough, also manages to be one of his warmest and charismatic performances ever. Fitting, too, given that Prine’s never been one to wallow in too much sorrow, and that his world-weary wisdom has always been told through an innocent perspective, no matter how dark the subject matter. It ends as we expect it to, with a goodbye that comes way too soon. Yet it’s also a powerful reminder of an artist who took nothing for granted, and cherished love the most from his experiences and memories. – ZK



“Sins of the Father”

Waylon Payne

Waylon Payne’s triumph over addiction is celebrated on “Sins of the Father,” which sources the origin of his problem back to the father that modeled bad behavior for him, but rejects it as an excuse for him following in his father’s footsteps.  In this celebratory moment of hard-earned redemption, he can’t be bothered to play the blame game.  If he’s going to forgive himself, he might as well forgive dad, too. – KJC




Taylor Swift

With “betty”– and its companion songs from folklore, “cardigan” and “august”– Taylor Swift is writing better songs about teenage drama now than she did when she was an actual teenager. The difference is in Swift’s newfound capacity for taking on the perspectives of the other people in the stories she’s telling. Here, she’s singing– very, very well, it must be said– from the perspective of a 17 year-old boy named James, but the song never suggests that James’ story is the only one that matters. Swift writes Betty and the other supporting characters with the recognition that they’re also people with their own interior lives: She’s worlds removed from the snippy, reactionary narrators of, say, “Picture to Burn.” That “betty” retains all of Swift’s technical gifts– the key change and POV shift in the final chorus are one of her trademarks for very good reasons– makes it perhaps the best single she’s ever shipped to country radio.  – JK



“You Were Mine”

Tami Neilson

I’ve long said that a song isn’t very good if the listener must know the tragic backstory behind it in order to ascribe meaning to it. Tami Neilson’s masterful “You Were Mine” is a perfect example of that rule in practice. Neilson was inspired to write “You Were Mine” following the death of her father. But, rather than writing a song of literal autobiography, she leaned into the difficult emotions of grief and considered how those feelings are applicable in other situations, and she channeled that grief into a break-up song for the ages. “You Were Mine” is a slice of country-blues that compares the end of a relationship to a rift in time itself: “There’s just before / And then there’s after you were mine.” There’s an acknowledgement that wounds may scar, but the damage is truly irreversible. 

The song is powerful on its own merits– again, the death of Neilson’s father figures into the song only in terms of the depth of her grief– but it’s Neilson’s performance that makes it one of the year’s finest singles. Neilson has proven her vocal prowess countless times over by now– she’s a regular fixture on our year-end lists– but she’s never committed something this guttural and raw to record. Every note she sings on “You Were Mine” is transcendent, making a case that she’s perhaps the finest vocalist in all of contemporary music. – JK



“Who You Thought I Was”

Brandy Clark

“Who You Thought I Was” is as clever as we’ve come to expect from Brandy Clark, but it’s also strikingly personal, lacking the narrative distance of her earlier work.  As she rattles off some of her former dreams of being Elvis and a cowboy in the sunset, it’s easy to miss that what she’s really doing is shifting her focus away from herself and on to her former partner.  She may have learned her lesson a little too late to save this relationship, but she’ll get it right the next time around. – KJC



“Small Town Hypocrite”

Caylee Hammack

Top to bottom, this list boasts some of the finest songwriting we’ve covered here at Country Universe in any of the years since I joined the crew. 2020 was an exceptional year for country music’s songwriters, even if country radio remained oblivious to the genre’s best work. More than any other, one particular verse stuck with me throughout the year, and it’s from Caylee Hammack’s “Small Town Hypocrite.” The entire song is a marvel of structure and wordplay, but the second verse is just extraordinary:

And that scholarship was a ship that sailed

When I chose you and daddy gave me hell

I made myself into someone else just to love you

And damn, I loved you.

Took all my plans and I put ‘em in a box,

Phantom pains for the wings I’d lost,

Had me circling rings in catalogues

For seven years, and you never got the hint.

The individual lines are impressive enough– that phantom pains reference is an all-timer, as is the slant rhyme of “sailed” and “hell,” as is the dropping of the rhyme scheme altogether to emphasize the last line, as is literally all of it– but it’s the overall tone that lingers. There’s a lifetime of regret packed into just those eight lines: Of squandered potential, familial disappointments, self-denial, frustration over lost time and opportunity.

Country music lives and dies by sad songs, but few songs are autobiographies without a protagonist. Hammack’s narrator is in no way empowered by her telling of this story: It’s not clear that she even knows who she is anymore, and she damn sure doesn’t like the person she’s describing. “Small Town Hypocrite” is about a series of decisions that, one by one, strip the narrator of her agency, until she’s at a point that she can do little more than shrug and say, “Ain’t that some shit.” While that line might not be the most sophisticated lyrical hook, “Small Town Hypocrite” is the most dense and, yes, sophisticated country songwriting of 2020.  – JK



“Only Children”

Jason Isbell & the 400 Unit

There’s a thread connecting Jason Isbell’s best work, where here, this friendship christened in childhood that ended way too soon carries a not-so-subtle subtext: of the two people in this situation to succumb to their own vices, it could have just as easily been Isbell, and he knows it.

One can interpret it to a fault, I suppose, but the complex run of emotions ranging everywhere from guilt to anger and regret over feeling the wrong person was taken is the same empathetic viewpoint that’s colored Isbell’s best work. And there’s nothing like the ghostly, atmospheric swell running along the background to echo the sorrowful haunting still felt today. I said it, too – it’s as good as anything else he’s made yet, and that’s saying something, indeed. – ZK



“What are You Gonna Tell Her”

Mickey Guyton

It seems like a lifetime ago that Mickey Guyton debuted “What are You Gonna Tell Her.”  Throughout 2020, as we suffered through an isolating pandemic that disproportionally impacted people of color, and as we watched a long overdue racial reckoning dominate the streets and the airwaves, Guyton’s song continued to resonate.

In calling out the big lies, “What are You Gonna Tell Her” reveals uncomfortable truths.   Telling ourselves a whitewashed version of the past that makes us feel no action is needed in the present is what prevents a more equitable future.

Guyton’s willingness to acknowledge the barriers that have limited her own success is so powerful because the strength of her singing and songwriting proves her point.   This was the best written single of the year.  Nothing else came close.  Her performance was immaculate.   Radio executives cheered for it.   Then they refused to play it, building her up just to tear her down.

Somewhere right now, there is another talented little girl dreaming of country music stardom, and she looks more like Mickey Guyton than any of the handful of women on country radio right now.  She thinks she can be the one to make it, and she’s being told to dream big, blissfully unaware that an undeniable talent who looks just like her is being blocked at every turn.   What the hell are you gonna tell her?  – KJC


Best of 2020

Albums: Part One | Part Two

Singles: Part One | Part Two



  1. Sunny, Lydia, Mickey, Emily, Courtney, Amanda, Caylee, Tami, Sierra, Lori, Taylor, and Brandy all drop fantastic singles in 2020. Pam Tillis, The Chicks, and Shania Twain still sound amazing in 2020. They been putting out great music since the 1990’s and they proved in 2020, they still got it.

  2. Great choice of “What Are You Gonna Tell Her” for #1. (i see that her other 2020 single “Black Like Me” is at 36 and her EP is on the album list)

  3. Re. “Sleep At Night” and “Gaslighter”: True to form, and even though I am not all that wild about Jack Antanoff’s production on these songs, the Chicks have come up with more winners (and even more so with “March March”). It helps that 2020 was the most topsy-turvy year in their lives, and for that matter all of ours as well, as it bought out the best in their writing, vocal, and instrumental skills.

    Re. “Betty”: Again, I don’t know if I can ever be a Taylor Swift fan; but at the very least, she gained a significant amount of maturity and went rather deep into the early 1970’s Laurel Canyon acoustic folk/country playbook of Linda Ronstadt and Joni Mitchell on this song. More importantly, she seemed to take the hints about improving her voice so that, even with its occasional mannerisms, she isn’t quite as irritating as she had been a mere four or five years ago.

Leave a Reply

Your email address will not be published.

This site uses Akismet to reduce spam. Learn how your comment data is processed.