James Taylor
A meditation on a small town's decline, written as a soft eulogy sung in the voice of someone who watched the place rise and now…
decline of small-town America obsolescence and progress loyalty to place
Jason Isbell
A narrator sits at his dying father's bedside in a small town he's always known too well, and realizes only in that final vigil…
small-town claustrophobia estrangement from a parent grief and release
Paul Simon
A bitter recollection of a suffocating hometown, stripped of color and possibility, sung as a reunion piece by Simon and…
small-town claustrophobia loss of faith inherited identity
Bill Callahan
A quiet domestic love song disguised as an account of piloting a small plane together. The flight becomes a working metaphor for…
domestic trust shared control in partnership contentment
Gillian Welch
A traveler recounts a journey to a mythic, menacing place called Scarlet Town, where hospitality curdles into betrayal and…
betrayal mortality folk/ballad inheritance
Tears for Fears
A hushed, folk-tinged meditation on mortality, freedom, and devotion, addressed from an aging narrator to a partner he credits…
mortality and aging freedom versus reason devotion as salvation
Uncle Tupelo
A portrait of small-town stasis sung with the flat, unsparing eye of someone who grew up watching it happen. The song addresses…
small-town entrapment wasted time denial and self-deception
Margo Price
Margo Price sketches a small-town portrait of someone who left and never came good, using a specific failed person as a stand-in…
small-town decline broken promises generational failure
Margo Price surveys the transactional culture of Nashville's music industry from the vantage of a newcomer who has already been…
music industry exploitation gender and power authenticity vs. commerce
Carly Simon
This is a torch-song standard (best known from Sinatra's version) recorded by Carly Simon for a film soundtrack, and it's built…
insomnia and longing unrequited love the contrast between day and night
Mariah Carey
Mariah Carey's 1994 reading of the 1934 novelty standard turns a simple children's warning song into a full-scale gospel-pop…
surveillance and reward childhood obedience holiday anticipation
Townes Van Zandt
A ballad about a legendary Mexican bandit and the friend widely suspected of betraying him, told with the flattened affect of a…
betrayal and complicity myth-making versus truth exile and displacement
A restless travel song built on blues repetition, where the highway and its trucks become both an escape route and a kind of…
restlessness and flight addiction/escape as motion transience and homelessness
An early, stripped-down Townes Van Zandt song told as a first-person litany of ruin — abandonment, drink, a bad romance, a…
fatalism cyclical poverty and violence addiction as companionship
This is a Rolling Stones cover (Jagger/Richards) performed live by Townes Van Zandt on Roadsongs, and in his hands the song's…
class resentment addiction and self-destruction romantic betrayal
A traveling songwriter's meditation on impermanence, love without possession, and the necessity of moving on, framed as both a…
impermanence itinerant life love without attachment
A short, quiet meditation on unspoken love and loss, built almost entirely from conditional wishes and unresolved arithmetic.…
unrequited love denial and repression escape and freedom
A weathered ballad about a Mexican bandit and the friend who may have betrayed him, told with the flat, elliptical tone of a…
betrayal and guilt myth-making and unreliable legend exile and diminishment
A ramshackle blues about a broke, drink-craving gambler whose fantasies of easy money and easy love curdle into a confession of…
poverty and want drink and gambling as fate violence disguised as bravado
Pearl Jam
A cover originally written by Victoria Williams, this Pearl Jam rendition tells the story of a marginalized, possibly mentally…
outsiderhood and stigma small-town cruelty and complicity fear versus compassion
A breezy, sing-song surface hides a small, deadpan love story about a sailor and a small-town girl. Paul Simon builds the song…
nostalgia innocence and Americana romantic idealization
Big Star
A deceptively simple slice of teenage boredom set to a chiming, anthemic riff, this song turns the aimlessness of small-town…
teenage boredom small-town aimlessness friendship
A dedication-turned-elegy for the defeated, this early Uncle Tupelo track surveys small-town despair and quietly asks whether…
small-town despair alcohol as coping mechanism spiritual exhaustion
The Shins
A hushed, melodically sweet song about romantic regret and a wish to shed adult disappointment carries lyrics that are far more…
regret and self-recrimination longing for innocence small-town disillusionment
Kacey Musgraves
A small-town portrait built on nursery-rhyme wordplay, this song surveys the quiet addictions, forced marriages, and inherited…
small-town stagnation inherited expectation quiet addiction
Grandaddy
A loose, dreamlike catalog of small-town wreckage - shut-down factories, joyriding teens, a decrepit limousine, a spray-painted…
small-town decay aimlessness and boredom mechanization versus nature
Steely Dan
A neighborhood gang works itself into a fever pitch preparing for the homecoming of a woman named Josie, whose arrival promises…
homecoming as ritual collective male desire violence disguised as celebration
Tom Waits
A road-worn ballad about a woman who flees a judgmental small town for California and ends up broke and cold in a motel, with a…
small-town judgment and shame escape and disillusionment poverty and survival
Gillian Welch strings together a series of small-town obituaries and rumors — an overdose, a runaway, a breakdown, a possible…
mortality and fatalism small-town gossip and rumor addiction and ruin
Beck
A quiet, weary breakup song in which the narrator addresses a partner who is emotionally unreachable, cataloguing small signs of…
romantic exhaustion emotional withdrawal resignation
Hank Williams
This Luke The Drifter recitation-style song tells a small parable about a gossiping neighbor and the woman she condemns,…
hypocrisy gossip and reputation moral judgment
Bruce Springsteen
A young man on a porch pleads with a woman named Mary to leave their fading town with him, framing an escape by car as both…
escape and flight romantic persuasion as salvation small-town limitation
R.E.M.
A country-tinged plea to someone about to leave town, in which the narrator's stated reasons for wanting them to stay keep…
fear of abandonment small-town stagnation vs. escape emotional denial
A narrator processes the disappearance of someone close by insisting she isn't actually dead, just gone and hiding in plain…
disappearance and denial isolation unreliable information
Chris Stapleton
A plainspoken love song built on a single conceit: material poverty offset entirely by romantic abundance. Stapleton uses the…
love versus material wealth contentment in poverty devotion
George Jones
A novelty-tinged story song built on a bait-and-switch: an old man's admiring description of a car turns out to be a description…
nostalgia lost youth double meaning/wordplay
A short, circling song about a young woman stalling against the pressure to settle down—marriage, respectability, the expected…
deferred adulthood female autonomy vs. domestic expectation escape and mobility
A breakup song built around a single, escalating image: the narrator drinking hard enough to kill off her own conscience so…
heartbreak and self-destruction alcohol as anesthetic hardened self-protection
Japanese Breakfast
A song written from the point of view of someone left behind by a person who's moved on to a bigger life, framed as a letter of…
unrequited devotion being left behind longing and patience