The Top Ten Americana Songs of All Time: Andrew Frolish

As ever, with features of this type, a great deal more time was spent reflecting, taking notes and re-listening to a huge number of great songs than was actually spent on the writing. Like most of my fellow writers, I started with some questions about what we were really looking for. I believe that these songs have influenced other artists or, perhaps, will provide such inspiration for the musicians of the future. Beyond great musicality, technical instrumentation and arrangements, these songs – like the best americana – move beyond the music and have a lasting emotional impact or say something profound about the human condition. A vital aspect of the best americana is lyricism and, for this list, I wanted to showcase songs with a sense of poetry and real lyrical intent, songs that tell stories and make us care about how they unfold. So, what follows is a set of songs that are inspiring, demonstrate technical and musical gifts, and have lyrical purpose and ambition.

Having established some parameters, then came the long-list. I started with 31 different artists, some of whom had multiple songs I could have justified including. In the past, I have written passionately about some of those who were ultimately omitted. Many of my favourite artists have produced a wonderful collection of songs over the course of storied, acclaimed careers but, perhaps didn’t have a single standout song for this list. A perfect example is Lucinda Williams who was number 2 on my list of greatest-ever artists in 2023 but doesn’t feature below; I love her artistry and overall contribution to americana but no one song hit the high bar. Others will disagree vehemently, I know! For similar reasons, I didn’t find a space for Son Volt, Robert Plant, Alison Krauss, Gillian Welch, Steve Forbert, Jerry Joseph, Drive By Truckers and Kris Kristofferson. Some songs were represented until the very final stages, including Kathleen by Josh Ritter and The Sea & The Shore by Amy Speace and John Fullbright. I think Bruce Springsteen, one of my favourite artists, has two parallel careers: one as the stadium-filling rock star and as one of the finest americana songwriters (Nebraska, The Ghost of Tom Joad, Devils & Dust, The Seeger Sessions and Western Stars – an extraordinary sequence of albums). I would class Nebraska as one of the best americana albums of all time but it’s a treasured body of work that is greater than the sum of its parts – none of the individual songs quite make this list in their own right. A special mention must go to a couple of outstanding duets: Company of Friends by Danny Schmidt and Carrie Elkin and Your Heart Belongs to Me by Jarrod and Claire Dickenson. Both of those glorious songs would probably be on a list of personal favourites, but that’s not quite what we were looking for here. So, here we go.

Number 10. Courtney Marie Andrews May Your Kindness Remain from May Your Kindness Remain (2018) 

A few years ago, I included Courtney Marie Andrews, relatively early in her career, in my list of the best americana artists of all time, claiming that she is, “… one of those artists that I think we’ll be listening to many years from now”. I stand by that. Her honest, wistful stories of love and loss are irresistible and truly the stuff of life. Emotionally resonant, her songs are thoughtful, poetic, vividly rendered windows into the lives of others. Hers are songs of everyday people, stories of the disenchanted and dispossessed, and, as such, have an authenticity to match their compassion. They are also infused with some special ingredients: lightness, hope and positivity. May Your Kindness Remain is inspired songwriting. it unfolds with quiet, understated beauty before growing and swelling with the drama of its truth. Andrews’ reflective words, lifted up on her lilting voice, deliver a wonderful message: “The richest of people aren’t rich with houses, cars, or fame.” Money runs out. Good looks fade. Kindness remains. Compassion is the most valuable thing we can offer in this world.

Number 9. Rhiannon Giddens At the Purchaser’s Option from Freedom Highway (2017)

An incredibly gifted multi-instrumentalist, Rhiannon Giddens transcends her music by writing about significant, weighty themes with great sensitivity. She is much-admired for her work with the Carolina Chocolate Drops. However, Giddens’ solo work is what places her in this list of all-time greats. Her banjo and fiddle-playing are hugely impressive, as are the quality and tone of her vocal performance – her pure, clear voice and range captivate and convey great emotion. It’s her songwriting and craft, though, that elevate her above many of her talented peers. Whether through more forceful songs or through her delicate balladry, Giddens reveals truths and connects deeply with her audience. The reflections may be personal or historical but she makes her subjects matter to everyone. Giddens’ second solo release, Freedom Highway, which won the International Folk Music Awards Album of the Year, is a truly important piece of work; artful and revelatory, this is music that carries the burden of great social and cultural significance, and carries it with subtle grace. Her words in At the Purchaser’s Option are heavy with hurt and hope, struggle and spirit: “You can take my body, you can take my bones // You can take my blood, but not my soul.” Simply put, this is a great song – a confluence of poetry, cultural significance and musicianship.

Number 8. Uncle Tupelo Graveyard Shift from No Depression (1990)

No Depression provided the blueprint for all that americana could be. That blend of genres is best represented by the opening track, Graveyard Shift, which takes roots music and twists it into something entirely new, shot through with distorted guitars and a punk sensibility. It’s raw and gritty and energised. Heartbeat percussion and a hypnotic repeating riff drive the song forward and so it comes, in waves and movements that sweep us along. Graveyard Shift earns its place on this list because of its great influence on so much music that followed, music that combines styles, knocking down the barriers between its music that plays with, then abandons, genre, refusing to be cast or pinned down, music that rebels and revels in inventive freedom and makes a virtue of its recklessness. And it’s a damn fine song.

Number 7. Townes Van Zandt Pancho and Lefty from The Late Great Townes Van Zandt (1972)

Some years ago, I had the pleasure of interviewing Daniel Antopolsky, a singer-songwriter who toured with Townes Van Zandt back in the 1970s. The pair visited Guy Clark together as well as travelling around Nashville, Colorado and Texas in Antopolsky’s old Ford van. On one occasion, Antopolsky even saved Van Zandt’s life by performing CPR on him after a heroin overdose, an event that led Antopolsky away from the music industry for many years as he sought out a more spiritual existence. The pair were together in a motel room, stuck in Denton, TX, when they decided to each write a song at the same time. Antopolsky wrote Sweet Lovin’ Music while Van Zandt wrote one of his best-known songs, Pancho and Lefty. Daniel told me: “I went outside to sit under the oak tree and then we came back and Townes had written ‘Pancho and Lefty’. I was the first person in the world to hear it!” It’s said that the two famous characters in Van Zandt’s song reflected the real-life relationship and life on the road that the pair shared at the time; indeed, legend has it that Lefty is based on Antopolsky. Talking to Daniel is a lovely memory for me because it’s not every day that you get to meet a fictional character from a famous Townes Van Zandt song. Van Zandt’s fluttering, finger-picked guitar and clear, pure, storytelling vocal style has become synonymous with the very idea of an American singer-songwriter and a huge number of artists cite him as an inspiration, including the likes of Steve Earle. Pancho and Lefty is perhaps the best example of Townes’ poetic, lyrical narrative style and beautiful mournful melodies. He created characters that could populate novels and films, authentic people with tales to tell that have influenced songwriters ever since.

Number 6. The Delines Kid Codeine from The Sea Drift (2022) 

I flitted between various songs by The Delines before settling on Kid Codeine. Little Earl, Colfax Avenue and The Imperial were all on the list at one time or another. In the end, Kid Codeine won out because of the well-realised characters, particularly Kid Codeine herself, who goes to great lengths to present herself to the world in a certain way, from her bouffant hair to wearing a fur coat to go and buy milk. Willy Vlautin is a great author, one of the finest around today, who is able to convey a vision of American life and pull us into the everyday lives of its everyday people. In his song lyrics, he manages to compress a novel’s-worth of cinematic detail into just a few short verses – an incredible skill. Kid Codeine does this so well; within a few lines the tragedy of this couple is revealed to us while the keys, brass, pulsing percussion and characterful voice of Amy Boone make it feel like an expansive movie soundtrack. As a long-time fan of boxing, the tale of a broke boxer past his best also appeals to me and my favourite of Vlautin’s novels is Don’t Skip Out on Me for the same reason. I’ve had the pleasure of chatting a couple of times to Vlautin – also a boxing fan – about related fiction. A couple of book recommendations from Willy Vlautin himself are Leonard Gardner’s Fat City and Rope Burns by F.X. Toole.

Number 5. Rosanne Cash September When it Comes from Rules of Travel (2003)

Without question, Rosanne Cash is one of my favourite musicians of all time. She brings such feeling and humanity to her songs through her deeply-sensitive lyrics and exceptional vocal delivery, and she has done this consistently for so many years. The tunefulness of Seven Year Ache or cleverness of A Feather’s Not a Bird could have made this list. Once, the wounded The Wheel made me shed a genuine tear while leaning on the barrier at the front of one of her shows. However, I’ve gone for September When it Comes because of its great emotional weight and intensity. The duet with her father is so impactful, exploring aging, impending loss and familial love. September When it Comes is tender, restrained and honest – all signs of great songwriting – and the result is devastatingly poignant and moving. This is what it means to be human.

Number 4. Levon Helm The Mountain from Dirt Farmer (2007)

Drummer and vocalist for The Band, Levon Helm’s solo work is full of warmth and compassion and his was one of the first names on my list. Levon Helm’s earthy, lived-in voice is perfect for telling stories like The Mountain. With banjo, fiddle, mandolin and a brilliant Southern groove, along with its lyrical narrative and sense of place, this is a great expression of what country, folk and americana music is all about. Helm’s words cleverly explore the passage of time and change, our ties to our roots and the impact of humanity on the landscape, as his narrator haunts the mountain on which he was born and worked his whole life. The Mountain features on Dirt Farmer, one of Helm’s later records that seemed to define his legacy. The album won the GRAMMY Award for Best Traditional Folk Album in 2008 and deservedly so. Helm’s music is full of heart and soul and authentic American life.  In The Mountain, his voice may be weathered but it isn’t weary – it’s exuberant, strong and vital.

Number 3. Johnny Cash Hurt from American IV: The Man Comes Around (2002)

The video for Johnny Cash’s version of Hurt is one of the most emotionally impactful ever. The way June looks at Johnny and the way he closes the fallboard over the keys at the end are such poignant moments. The images and symbols of love and loss are quietly devastating and make us reckon with our own mortality. Musically, Cash transforms the song into the deepest expression of humanity in all its pain and futility. It goes without saying, that he made Hurt his own and when he sings, “Everyone I know goes away in the end,” the weight of this truth is heavy on the heart. That he sings these emotive lines so close to the end of his life, in the context of personal loss, makes it all the more powerful. Although the arrangement is subtle and begins delicately, the song builds up to a climax of pounding keys, and pulsing, unresolved tension; we are left immersed in reflective feelings of regret, grief and loss. This is the feeling of farewell in musical form and, possibly, the best cover of all time.

Number 2. Jason Isbell and the 400 Unit If We Were Vampires from The Nashville Sound (2017)

The introductory guitar notes in If We Were Vampires are simply beautiful, as is the vocal melody throughout. However, what makes this song so special is the way that Isbell manages to capture the most elusive of themes: our relationship with time. His words blend personal detail with the universal experience perfectly before the hard acknowledgement that, “Maybe time running out is a gift”. The most overwhelming idea in the song is, “It’s knowing that this can’t go on forever”. The words are simple and direct and truthful. The fact is that we all do know, deep down, that this life and our loving relationships will not go on forever. Indeed, its blindingly obvious but, if we dwelled on this too much or too long, we might struggle to function so we compartmentalise it. To have this truth spelled out in such musical beauty is utterly disarming. This is a song I can listen to over and over again and, when I do, I feel touched by the profound.

Number 1. John Prine Angel From Montgomery from John Prine (1971)

The iconic John Prine was always going to be celebrated in this list. An influential figure and inspiration to many, he was one of the recipients of the GRAMMY Lifetime Achievement Award in 2020 and what a musical lifetime it was. The likes of Brandi Carlile, Sturgill Simpson and Jason Isbell acknowledge his influence on their work. Prine did it all: personal narratives, fictional tales, protest songs, explorations of worthy themes and songs that address everything that is central to the human condition and what this life is all about. That he did it with such humour, whimsey and poetry makes his songcraft all the more distinctive and accessible. His storytelling genius and wit helped him to create a huge volume of emotionally resonant songs. My favourite of Prine’s songs is probably Sam Stone. Whenever I think of the importance of lyrical intent and themes in Americana, the line, “There’s a hole in daddy’s arm where all the money goes”, from that song always comes to mind immediately. However, I’ve chosen Angel from Montgomery for this list because it goes beyond personal preference – it’s universally revered and has been covered countless times by the likes of Bonnie Raitt, Carly Simon and John Denver. Prine inhabits the character of an older woman so effectively and delivers a wish that many can associate with: that something will transport us away from the lives we’re living in and relationships we’re stuck in. It’s a quietly-desperate song of hope for something more: “Just give me one thing that I can hold on to // To believe in this livin’ is just a hard way to go”. Prine’s vivid imagery and raw, emotive narrative in Angel from Montgomery make this a true cornerstone of American songwriting. Tuneful and timeless and heartfelt, Prine’s songs just make us all care that little bit more.