A Serendipitous Duet: How Two Generations Found Common Ground in a Timeless Tune
Ah, if ever there was a song to stir the deep currents of memory and tender melancholy, it’s “How Lucky” by Kurt Vile featuring the incomparable John Prine. Released on October 2, 2020, as part of Kurt Vile’s EP, Speed, Sound, Lonely KV, this duet arrived in the world under a heavy sky. Just months after John Prine’s passing in April 2020 due to COVID-19, this recording served as a poignant farewell, a final studio gift from a beloved troubadour. It wasn’t just a cover; it was a conversation across generations, a bridge between a living legend and a fervent admirer, recorded in late 2019, making it one of Prine’s very last studio recordings. The song garnered considerable attention, with Prine making his first ever appearance on a Billboard airplay chart when “How Lucky” debuted at No. 28 on the Adult Alternative Songs tally in October 2020 – a testament to the enduring power of his music, even in his absence, and the fresh appeal Kurt Vile brought to it.
For those of us who have lived a few decades and seen the world change, “How Lucky” resonates with a profound sense of reflection on time’s relentless march. The song itself, originally appearing on John Prine’s 1979 album, Pink Cadillac, is a masterpiece of his signature narrative style. It paints a picture of a man revisiting a familiar street after a long absence, only to find it transformed, almost unrecognizable. “There were signs that I remembered / And some that I don’t recall,” the lyrics muse, capturing that bittersweet realization that while places evolve, our memories of them remain frozen in time, tinged with a longing for what once was. It’s about the constancy of change, and the almost miraculous fortune of holding onto the good, even as the landscape shifts around us. As one listener so eloquently put it, the song reminds us to “take stock of the good things,” even when life feels overwhelming. “I bronzed my shoes and hung ’em from my rear view mirror,” a particularly evocative line, speaks to a desire to preserve cherished moments, perhaps even in the face of inevitable regret or the things we wish we could alter. It’s about finding the silver lining, the quiet joy in simply having experienced those moments, imperfect as they may have been.
The story behind this particular duet adds layers of emotional depth. Kurt Vile had long considered John Prine a hero. The opportunity to record with him was, for Vile, a dream come true. Imagine the scene: in Nashville’s hallowed Butcher Shoppe studio, under the guidance of David “Fergie” Ferguson (a renowned engineer who also worked with Johnny Cash), Vile and Prine came together. Vile recounted being “floating and flying” and almost unable to process what Prine was saying to him, such was his awe. It’s a charming image, the younger artist star-struck by the master. Vile had already recorded a cover of Prine’s “Speed of the Sound of Loneliness” for the EP, which Prine himself had heard and liked, a small but significant endorsement that undoubtedly emboldened Vile. This duet on “How Lucky” was “probably the single most special musical moment” in Vile’s life, and you can feel that reverence in the gentle, almost tender way he approaches the song.
What makes this rendition so special, especially for us older listeners, is the way Kurt Vile’s contemporary, almost laconic vocal style blends with John Prine’s wise, weathered voice. Vile’s contribution isn’t just a carbon copy; he adds his signature meandering guitar work, a touch of mandolin, and a casual warmth that makes the song feel less like a performance and more like two friends jamming on a porch, reminiscing about days gone by. Prine’s voice, aged but still full of that familiar sparkle and wit, carries the weight of decades of experience, making the song’s reflective lyrics even more potent. When their voices intertwine on that final verse, “There was all these things that I don’t think I remember,” before realizing, “Hey, how lucky can one man get,” it’s a poignant, almost spiritual moment. It’s a passing of the torch, a shared understanding of life’s unpredictable beauty and the quiet grace of gratitude. This version isn’t just a musical collaboration; it’s a profound statement on legacy, admiration, and the simple, enduring power of a well-told story, made even more precious by the fact that it marked one of John Prine’s last gifts to the world. It reminds us that even when our heroes depart, their wisdom and their music continue to resonate, guiding us to appreciate the “how lucky” moments that shape our own long roads.