What makes a truly great song? This is the question I had to wrestle with when compiling this list of what I believe to be the best Americana songs of all time. As I was putting it together, I came to realise that, for me at least, so much of it is down to the lyrics. If the storytelling isn’t rich enough and the words don’t strike the right note poetically, then it can turn an otherwise solid song into a miss. I’m not going to pretend I’m not a little bit biased though since I consider myself a fan of the wider bodies of work of all the artists whose songs I’ve listed, but I do really believe these tracks to be the best of the best and just maybe, I’m not the only one.
10. Chris Stapleton ‘Tennessee Whiskey’ (“Traveller” 2015)
Sometimes, it’s not the artist who originally releases a song that records what comes to be its defining version. ‘Tennessee Whiskey’, written by songwriters Dean Dillon and Linda Hargrove, was first released by David Allan Coe on his 1981 album of the same name, and it gained only minor success. George Jones went on to release his version in 1983, which was more successful than Coe’s, but the song didn’t reach new heights until Chris Stapleton came along and put his own stamp on it. The ballad about the intoxicating power of love gained not just a new injection of soul from Stapleton’s unmistakable vocals, but also a whole new level of mainstream recognition for how brilliant it is.
9. Brandi Carlile ‘The Story’ (“The Story” 2007)
I actually feel a little guilty that the Brandi Carlile track I chose for this list wasn’t written by Carlile herself (instead it was written solely by Phil Hanseroth, one of the two brothers who remain part of her band), but ‘The Story’ has that epic, career defining quality in a way nothing else from her discography quite touches. Carlile’s vocals are as strong as ever, soaring beautifully as she so powerfully sings of the desire for another to witness and share with her the ups and downs that life brings.
8. Father John Misty ‘Pure Comedy’ (“Pure Comedy” 2017)
As great as Josh Tillman is when drawing from his own personal experiences, when he takes on the wider world, it becomes something really special: “Just wait until the part where they start to believe / They’re at the center of everything / And some all-powerful being / Endowed this horror show with meaning”, he sings on the chorus of ‘Pure Comedy’, inspired by not just religious worship, but the God-like status some humans have been falsely awarded in recent years, making it depressingly more relevant now than it was when it was released in 2017, but brilliant none the less.
7. The National ‘Fake Empire’ (“Boxer” 2007)
“Stay out super late tonight / Picking apples, making pies / Put a little something in our lemonade / And take it with us”, come Matt Berninger’s deep but dulcet tones on The National’s anthem to escapism ‘Fake Empire’. The concept is a simple one really: when life gets too much, live in your own, more pleasant imaginary world. It’s an idea that if done the wrong way, could come off as cheesy, but of course The National are able to get the tone just right, grounding fairytale imagery with their signature sound in a way that’s quite unforgettable.
6. Townes Van Zandt ‘Waitin’ Around to Die’ (“Townes Van Zandt” 1969)
“Sometimes, I don’t know where this dirty road is taking me / Sometimes, I don’t even know the reason why” could very well be autobiographical words by Townes Van Zandt, but they are in fact lines he wrote after meeting a man in a bar who inspired him to craft a tale of a soul who has lost themselves to addiction and ends up caught up in crime. It’s a dark subject, but Van Zandt tackles it in that effortless way he always seemed to be able to do, and if only he had lived past his 52 years, who knows what other stories he could have potentially still been delivering.
5. The Chicks ‘Not Ready to Make Nice’ (“Taking the Long Way” 2006)
In the insane political landscape that is 2025, it’s kind of hard to imagine the controversy Chicks lead singer Natalie Maines caused in 2003 when she criticised then American President George W. Bush, but her comments incited so much anger that the band were pulled from country radio and shunned by the community around it: ‘Not Ready to Make Nice’ was their unapologetic response. Co-written by the band with Semisonic’s Dan Wilson, it opens with the defiant “Forgive, sounds good / Forget, I don’t think I could”, and only grows more obstinate from there in a way rarely seen before or since by such a mainstream act.
4. Counting Crows ‘A Long December’ (“Recovering the Satellites” 1996)
“I knew that was the best thing I’d ever written when I wrote it”, Counting Crows frontman Adam Duritz admitted of ‘A Long December’ and while this hubris might seem unfounded in some artists, when you’re talking about a song with a verse like “The smell of hospitals in winter / And the feeling that it’s all a lot of oysters, but no pearls / All at once, you look across a crowded room / To see the way that light attaches to a girl”, it feels entirely justified. Duritz also said recently that he “knew it was a perfect song” and that he “knew [he] was going to love playing it for ever”, which is great news for us all.
3. Jason Isbell ‘Cover Me Up’ (“Southeastern” 2013)
In recent years, Jason Isbell’s ‘Cover Me Up’ has become something of a standard with many artists covering it, notably Morgan Wallen on his second album (Isbell wisely donated all the profits he made from it to the Nashville chapter of the NAACP), and just this month, somewhat unexpectedly, by rising popstar Benson Boone during a Nashville tour stop. It’s easy to see why so many people have fallen in love with it. It’s a song Isbell wrote about falling in love with now ex-wife Amanda Shires, getting sober and most of all, wanting to spend forever ensconced in a bubble with her away from the world.
2. Joni Mitchell ‘A Case of You’ (“Blue” 1971)
“Blue” is arguably Joni Mitchell’s magnum opus, so putting something from it on this list was a no-brainer; what did take a considerable amount of thought however was which track it was going to be. To overlook classics like ‘River’ and ‘California’, it had to be one special song, but ‘A Case of You’ most certainly fits that bill. “Just before our love got lost you said / ‘I am as constant as a northern star’ / And I said, ‘Constantly in the darkness / Where’s that at? / If you want me I’ll be in the bar’”, must certainly be the greatest opening lines ever, ones that set you up for the poetic heartwrench to come when Mitchell sings of someone that’s touched her so deeply, she can’t let them go.
1. Jeff Buckley ‘Lover, You Should’ve Come Over’ (“Grace” 1994)
I feel like choosing from Jeff Buckley’s one and only masterpiece of an album “Grace” should have felt more challenging than it did for me, but as brilliant as ‘Last Goodbye’, ‘Dream Brother’ or ‘Mojo Pin’ may be, no other song will ever have my heart in the way the sprawling, tragic ‘Lover, You Should’ve Come Over’ does. Buckley is having a bit of a moment, and there’s even a new documentary about him using one of the most memorable lines from the song as the title (“It’s Never Over”), which is by all accounts pretty great, but it’s never going to be a patch on the song it borrows from. “My body turns and yearns / For a sleep that won’t ever come”, he bro0ds in a way that once heard, will haunt you forever.
Excellent choice. wouldn’t argue with any of those.
Some I know some I don’t and that’s a good thing. Often such lists are based on sales as if that’s a vindication of taste and lists by those who use them as evidence.