Jason Isbell, a name synonymous with profound lyricism and authentic Americana music, stands as a beacon for those who appreciate storytelling woven into song. As he geared up to release his fifth solo album, Something More Than Free, back in 2015, the anticipation was palpable. Isbell had already carved a niche, residing in that rich, yet vaguely defined space between rock, folk, and country, often labeled Americana. Within this realm, many crowned him the king of poignant lyrics. His craft lies in penning affecting narratives about genuine, relatable characters dwelling in the often-overlooked landscapes of middle America. At 36 then, Isbell masterfully gave voice and agency to the invisible—the barflies, the working-class heroes in service industries, the young parents grappling with adulthood. His songs, at their zenith, possess the power to grip your heart and leave you breathless.
Something More Than Free was poised to amplify the successes of its predecessor, 2013’s Southeastern, an album deeply marked by Isbell’s journey into sobriety. In contrast to the heavier, riff-driven sound of his Drive-By Truckers days, Free leaned towards acoustic textures and nuanced reflections. It delved into personal growth and the grounding force of family bonds that had steered him away from the edge. Listeners were warned: prepare for emotions akin to a Friday Night Lights binge-watching session.
In anticipation of Something More Than Free, a curated list of Jason Isbell’s top 10 most emotionally resonant songs was compiled, prompting Isbell himself to offer insights into each track and his songwriting ethos. This exploration aims to delve deeper into these selections, offering an enhanced perspective for fans and newcomers alike, all while keeping the focus firmly on the compelling artistry of Songs By Jason Isbell.
10. “Speed Trap Town” (Something More Than Free, 2015)
“Speed Trap Town,” a gem from Something More Than Free, immediately captivates with its in medias res opening. The scene unfolds in a grocery store, a mundane setting for a heart-wrenching revelation: “She said, ‘It’s none of my business, but it breaks my heart’ / I dropped a dozen cheap roses in my shopping cart.” This narrative technique, starting mid-story, is a signature Isbell move. He acknowledges having a broader narrative in mind but understands the power of concise storytelling in songwriting. In the limited space of a song, only the most crucial details can survive. He admires this approach in other artists, citing a Ben Howard song where the opening line throws you directly into a moment of distraction and unspoken tension.
Isbell notes a shift in his songwriting process towards more rigorous editing. Gone are the days of solely relying on immediate inspiration. He emphasizes the value of diligent work, a perspective sharpened by owning his record label, granting him the luxury of time and meticulous crafting. Sobriety plays a crucial role here, enabling him to dedicate hours to a song, replacing the urge for impulsive distractions with focused creation. “Speed Trap Town” is a testament to this refined approach, a masterclass in understated storytelling within a tight frame. The song subtly paints a picture of small-town desperation and unspoken goodbyes, resonating deeply with its poignant brevity.
9. “Songs That She Sang in the Shower” (Southeastern, 2013)
Another song that plunges directly into a vivid scene, “Songs That She Sang in the Shower” also showcases Isbell’s fondness for interweaving song references. The inclusion of Dusty Springfield’s “Breakfast in Bed” and Pink Floyd’s “Wish You Were Here” isn’t arbitrary. Isbell reveals that while he had numerous options, these particular songs resonated most with the character he was crafting. The choices weren’t merely about rhyme scheme; they were about reflecting the musical soul of the person he was depicting.
He elaborates that the character is someone who, like many in his circle, appreciates a diverse spectrum of music. This detail becomes a subtle yet powerful way to convey the depth and complexity of the missing person at the heart of the song. The referenced songs become sonic brushstrokes, painting a richer portrait of longing and remembrance. “Songs That She Sang in the Shower” isn’t just about missing someone; it’s about missing their unique soundtrack, the intimate musical landscape they curated in their everyday life. This song underscores Isbell’s ability to use specific cultural touchstones to build deeply personal and relatable narratives.
8. “The Devil Is My Running Mate” (Sirens of the Ditch, 2007)
“The Devil Is My Running Mate” emerges from Isbell’s earlier work, from the album Sirens of the Ditch. Isbell admits he hadn’t revisited this song in quite some time, readily identifying it as overtly political. While it might stand out in his catalog for its direct anger, Isbell clarifies that his political commentary is usually more nuanced, embedded within the stories of ordinary people striving to navigate life.
The interviewer points out the song’s unusual directness in its anger, a departure from Isbell’s typical implicitly political songwriting. Isbell explains his belief that politics are deeply personal and that individual stories can reflect larger societal truths. He shies away from broad, generalized statements, finding them ineffective in songwriting. Instead, he opts for a smaller, more personal lens through which to explore political themes. “The Devil Is My Running Mate” serves as a potent, if less typical, example of songs by Jason Isbell that engage with the political landscape, albeit through a distinctly personal and emotionally charged perspective. It’s a raw expression of frustration, reflecting the anxieties of a specific moment in time, yet still resonating with broader themes of societal disillusionment.
7. “Daisy Mae” (Here We Rest, 2011)
“Daisy Mae,” from Here We Rest, delves into a deeply sensitive and often unspoken issue: the prevalence of sexual abuse. Isbell recounts a growing realization about the number of people he knew who had experienced childhood sexual abuse. This awareness, sharpened by personal relationships and maturing perspectives, moved him to address this painful reality in song.
He aimed to embody the perspective of someone in a relationship with a partner grappling with the long-term effects of childhood trauma. “Daisy Mae” is not just a song; it’s an attempt at empathy and understanding, shedding light on the often-hidden scars of abuse. Isbell expresses shock at the widespread nature of this issue, emphasizing the importance of acknowledging and confronting this painful reality. The song is a somber reflection on the lasting impact of childhood trauma on adult relationships, handled with Isbell’s characteristic sensitivity and lyrical precision. It’s a powerful reminder of the hidden burdens many carry and the importance of compassion and understanding.
6. “Children of Children” (Something More Than Free)
“Children of Children,” another track from Something More Than Free, explores the intricate dynamics of generations, a recurring theme in songs by Jason Isbell. This song specifically delves into the perspective shift that occurs as one ages and reflects on their parents’ youth and sacrifices. Isbell shares the personal inspiration behind the song: both he and his wife had very young parents. His mother was just 15 when he was born, and his wife’s mother was around 17 or 18 when she had her.
This shared experience prompted them to contemplate the “time that those people missed” due to early parenthood and the profound dedication they invested in raising their children. Isbell contemplates why this generational perspective fascinates him as a songwriter. He explains that these familial relationships are central to his life, and he strives to write about what he knows intimately. Coming from a Southern background, family ties are particularly strong. He highlights the interdependence within families, where generations often rely on each other for support. As one matures, parents are no longer seen as infallible figures but as complex human beings with their own flaws and strengths. This nuanced understanding of parenthood, Isbell suggests, marks a significant step in one’s own maturation. “Children of Children” beautifully encapsulates this evolving perception, a hallmark of insightful songs by Jason Isbell.
5. “Outfit” (Drive-By Truckers, Decoration Day, 2003)
The generational theme finds perhaps its most poignant expression in “Outfit,” a song from Isbell’s Drive-By Truckers era, featured on the album Decoration Day. This track is structured as a series of fatherly advice, imbued with both practical wisdom and deep affection. The question arises: was this advice directly imparted by Isbell’s own father?
Isbell confirms that “Outfit” was indeed inspired by his father’s guidance. While not verbatim, the song captures the essence of their conversations and his father’s core values. Some lines are direct echoes of his father’s pet peeves, while others reflect his sense of humor. The song is a mosaic of authentic paternal wisdom, drawn from real-life interactions. When asked about the central lessons his father wanted to instill, Isbell emphasizes the importance of family bonds, particularly staying connected with his sister and calling home. This resonates with the broader theme of relying on family, especially in times of need. “Outfit” stands as a timeless ode to fatherly love and guidance, a standout among songs by Jason Isbell for its warmth and heartfelt sincerity.
4. “Cover Me Up” (Southeastern)
“Cover Me Up,” from Southeastern, secures its place high on the list, famously known for its emotional impact even on Isbell himself. The anecdote of him choking up while first playing it for his wife, Amanda Shires, underscores its profound vulnerability. Isbell confirms this emotional reaction, stating it happened “the first 20 or 30 times probably.”
Described as the purest love song in his catalog, “Cover Me Up” begs the question: is vulnerability and happiness harder to express in song than darkness? Isbell admits it’s not easy. Writing such a song can feel uncool, challenging the stoic artist persona. However, he believes his role as a songwriter is to strive for honesty, even when it leads to uncomfortable emotional territories. He recounts attending a wedding where a non-musician friend sang a song for his wife. Despite not being technically perfect, its emotional sincerity was undeniable. This experience highlighted the profound difficulty and bravery in writing and performing a deeply personal love song. “Cover Me Up” was Isbell’s attempt at this, written before he and Amanda were married, adding another layer of vulnerability to the act. The stakes were high; a poorly received love song could have had dire consequences. Fortunately, Amanda’s discerning taste in music approved, solidifying “Cover Me Up” as a cornerstone of songs by Jason Isbell, celebrated for its raw honesty and tender affection.
3. “Danko/Manuel” (Drive-By Truckers, The Dirty South, 2004)
“Danko/Manuel,” from Drive-By Truckers’ The Dirty South, takes a poignant turn, inspired by Levon Helm’s memoir, This Wheel’s on Fire. The song was sparked by a passage about The Band’s dark humor pact: whoever died first, the others would ensure their burial back home. This dark camaraderie juxtaposed sharply with the tragic reality of Richard Manuel’s suicide during a low point for the band. Isbell was deeply moved by this story, especially as he was touring with his own band at the time, facing similar struggles with addiction, depression, and the precariousness of musical relevance. He saw a reflection of his own experiences in The Band’s narrative.
The interviewer questions if Isbell, in his youth, romanticized the self-destructive touring musician archetype. Isbell clarifies that he never truly romanticized it, having witnessed its harsh realities from the beginning. If anything, he “romanticized it as an excuse to keep going, and keep growing, and keep living that way myself.” His perspective on this lifestyle hasn’t fundamentally shifted. He was aware of its destructiveness but pushed forward until he reached a breaking point, no longer willing to endure constant suffering. “Danko/Manuel” serves as a somber reflection on the darker side of the musician’s life, a powerful addition to songs by Jason Isbell that explore themes of mortality, addiction, and the toll of the road.
2. “Goddamn Lonely Love” (The Dirty South)
For many songwriters, “Goddamn Lonely Love,” also from The Dirty South, would be their career-defining tearjerker. For Isbell, it’s the runner-up. This song masterfully evokes the specific feeling of isolation, intoxication, and haunting memories in a bar setting. Given Isbell’s sobriety and changed lifestyle, the question arises: can he still connect with this song in the same way?
Isbell affirms his connection, explaining he can still vividly recall the places and emotions that birthed the song. Time, he notes, feels compressed; the decade since writing it feels like mere months. Looking back to that period remains clear and accessible, a valuable tool for his songwriting. He acknowledges that songwriting isn’t always about the present moment; drawing from past experiences is crucial. Onstage, he still taps into those feelings, albeit with less intensity than a decade prior. “Goddamn Lonely Love” remains a potent example of songs by Jason Isbell that capture raw, visceral emotion, transcending personal changes and continuing to resonate with its timeless portrayal of loneliness and longing.
1. “Elephant” (Southeastern)
Crowned as “the saddest song of the millennium,” “Elephant,” from Southeastern, claims the top spot. Its emotional weight is so profound that even seasoned listeners might avoid it to prevent a day derailed by sorrow. The challenge with songs about sensitive topics like cancer is avoiding sentimentality and clichés. How did Isbell navigate these pitfalls?
His approach was to shift the focus away from cancer itself and towards the human relationship at its core. “I didn’t want to write about cancer as much as the relationship,” he states. He believes that while cancer itself is a limited subject in songwriting, the nuances of human relationships offer infinite depth. “Elephant” prioritizes the intimate connection between two people facing mortality, making the illness a backdrop rather than the central theme.
When crafting such an emotionally charged song, does Isbell immediately recognize its power? Unlike comedy, where audience feedback is crucial, “Elephant” resonated deeply with Isbell from its inception. “When that song was done, I knew that the knife was going to be twisted,” he recalls. He describes a growing ability to detach from his creations, allowing him to listen with a more objective ear. This might be attributed to his extensive songwriting experience. “Elephant” was written in a hotel room on a night off, and upon completion, its profound impact was undeniable. He compares the experience to hearing a song by another artist that deeply moves you. “It affected me separate from the creation of it.” “Elephant” stands as a testament to Isbell’s masterful ability to craft emotionally devastating yet profoundly beautiful songs by Jason Isbell, solidifying his reputation as a lyrical storyteller of unparalleled depth and sensitivity.
In conclusion, these ten songs offer a compelling journey through the emotional landscape of Jason Isbell’s artistry. From the raw political anger of “The Devil Is My Running Mate” to the heart-wrenching intimacy of “Elephant,” songs by Jason Isbell consistently demonstrate his lyrical prowess and his profound understanding of the human condition. Exploring these tracks is not just listening to music; it’s experiencing stories, emotions, and reflections that linger long after the final note fades.
