Paul Simon
A reunion single from Simon and Garfunkel that reads as a bitter anti-nostalgia song, dismantling the idea of small-town…
small-town disillusionment loss of faith suppressed violence
Townes Van Zandt
A ballad about a Mexican bandit's death and the shadowy figure who may have betrayed him, told with the flat affect of folklore…
betrayal and complicity myth-making versus truth exile and diminishment
Bruce Springsteen
A young man stands in a driveway trying to talk a woman named Mary into getting in his car and leaving town with him. Over five…
escape and flight the limits of romantic promise small-town decay
Gillian Welch
A short, circling ballad about a young woman fleeing domestic expectation for a taste of freedom before she settles into the…
deferred responsibility female autonomy vs. convention escape and fantasy
Joni Mitchell
A three-part meditation in which the speaker sets a naive, image-drunk way of seeing against a disenchanted one, then refuses to…
disillusionment the limits of knowledge aging and changed perception
Emmylou Harris
A narrator looks back at a childhood friend, Lillian, whose life in a small Southern town never escapes the gravity of that…
rural poverty and stasis female friendship the cost of unfulfilled ambition
Nick Drake
A brief autobiographical arc compressed into a handful of couplets, tracing a movement from innocence through disillusionment to…
loss of innocence depression and fatigue dependency on another
Leonard Cohen
A meditation on the pull between transcendence and the grinding routine of ordinary commerce and appetite, imagined as a street…
sacred vs. profane mortality and impermanence spiritual longing amid worldly routine
John Prine
Prine elegizes a real Kentucky town erased by strip mining, using a child's plea to his father as the frame for a broader story…
environmental destruction loss of home/place industrial 'progress' vs. nature
A three-part meditation in waltz time that moves from a woman by a river, to Christ walking on water, and back to the woman…
erotic love as spiritual apprehension faith and doubt surrender to a guide
Otis Redding
A man who has moved across the country sits by the water in San Francisco, watching ships come and go, admitting he is doing…
idleness and drift migration and displacement loneliness
Kate Bush
A song about two lovers who keep wounding each other without meaning to, and the narrator's fantasy of a supernatural fix: a…
empathy as an impossible exchange the violence hidden inside love gendered misunderstanding