James Blake
A song about retracting a breakup, or an attempted exit, before it's finished — the narrator tries to end things, can't, and…
ambivalence in love retraction and regret self-doubt
Smokey Robinson
A spare confession of regret builds around a single unanswered question: why didn't the narrator show up for someone waiting.…
regret emotional paralysis longing
Roberta Flack
A quiet, aching ballad built around a single conditional wish -- the hope of a reunion the singer knows may never come. Flack…
longing regret idealized love
Bill Withers
A man tracks down a former partner after learning she bore him a daughter he never knew about, and the song is essentially one…
absent fatherhood lost time betrayal and withheld truth
A late-night confession of loneliness dressed up as a blues lament, in which the narrator's supposed freedom and popularity…
loneliness within abundance regret disillusionment with casual sex
Nick Drake
A quiet catalog of unrealized selves, sung by someone who lists all the modest, useful things he might have become instead of…
unfulfilled potential self-doubt longing for ordinariness
Richard Thompson
A short, circling song built almost entirely around one unspoken sentence: the narrator never told a former lover he loved her,…
emotional inarticulacy regret unfinished endings
James Taylor
A spare, almost proverbial song about walking away from a failed relationship or a bad chapter of life, addressed as much to the…
self-recrimination forward motion as survival regret
George Jones
A late-career George Jones confession set as a plainspoken moral ledger: a man looking back on a life of drink and lost…
regret addiction free will versus fate
Rosanne Cash
Rosanne Cash's version of this traditional folk song turns a simple hitchhiker's lament into a meditation on permanent distance…
distance and displacement homesickness regret
Donny Hathaway
This is a live soul rendering of the Beatles standard, transformed from a chamber-pop miniature into an extended…
romantic loss nostalgia regret
Johnny Cash
A cover written originally as a young man's meditation on self-harm and numbness becomes, in Johnny Cash's version, an old man's…
mortality regret addiction and self-destruction
Willie Nelson
This is a cover of Coldplay's 2002 song, reinterpreted by Willie Nelson as a weathered, plainspoken confession of regret rather…
regret and apology the limits of reason against feeling longing for a return to simplicity
Al Green
A young man begs a train conductor to reverse course so he can return to a lover he left too hastily. Al Green, still developing…
regret and reversal longing isolation
Prince
A ballad of apology and release, built around an image—purple rain—that resists literal decoding but functions as a symbol of…
regret and apology romantic ambiguity spiritual transcendence
LCD Soundsystem
A song about a night out that becomes a meditation on an entire adult life, as the narrator watches youth-culture rituals repeat…
aging friendship and its erosion nightlife and nostalgia
Sufjan Stevens
A road-trip song about young adulthood as a series of impulsive reinventions, told through fragmented memory rather than plot.…
self-reinvention transience and travel romantic idealism
Mariah Carey
A breakup confession sung after the fact, where the narrator admits her own foolishness cost her a relationship she now realizes…
regret and self-recognition dependency and loneliness denial giving way to clarity
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
Maxwell
Maxwell's Unplugged reading of Kate Bush's ballad turns a song about a man helplessly watching his wife through a dangerous…
helplessness in the face of mortality regret over words and gestures withheld gendered division of labor and pain
Joni Mitchell
Joni Mitchell's early environmental protest song works as a series of loosely connected complaints -- about development,…
environmental loss commodification of nature nostalgia and regret
Portishead
A brooding trip-hop meditation on emotional dependency and self-alienation, built around a hypnotic vocal sample and a chorus…
emotional dependency numbness and self-alienation disillusionment
Alison Krauss
This is a classic torch song of concealed longing, performed here by Alison Krauss as a hushed, aching ballad. A speaker greets…
unrequited love emotional concealment missed opportunity
Joan Baez
Baez's early reading of this traditional ballad frames the singer as a woman recounting her own ruin, casting the House of the…
ruin and regret fallen woman narrative fate versus free will
Billy Joel
A comeback single that reads as both a reconciliation ballad and a piece of career autobiography, built around the plea of…
reconciliation neglect and regret time and lateness
A first-person prison lament in which the narrator, confined and hopeless, is tormented by the sound of a train he cannot board.…
confinement and freedom guilt and moral consequence class resentment
Townes Van Zandt
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
Harry Nilsson
A traditional-blues lament about the aftermath of a lovers' quarrel, delivered as a loose, almost improvisational vamp built…
heartbreak and regret isolation blues tradition
Kris Kristofferson
A plainspoken elegy for a lost relationship, built on unglamorous, specific praise rather than romantic cliché. The narrator…
loss and regret the ordinary made sacred restlessness vs. belonging
Bert Jansch
A quiet song of apology and remembrance, addressed to someone the narrator once let down and now recalls through fragments of…
regret and apology memory and nostalgia aging and loss of connection
Tears for Fears
A cool, synth-driven meditation on estrangement between two people who once knew each other well, built around the anxious…
emotional distance loss of identity regret and hesitation
Florence + the Machine
A confessional anthem about trying to physically expel guilt and self-recrimination, built around the image of dancing off a…
guilt and self-forgiveness cyclical regret catharsis through movement
Adele
A one-sided phone call to an estranged lover becomes a meditation on the impossibility of real repair. The narrator rehearses an…
unresolved regret failed communication nostalgia for youth
Nina Simone
Nina Simone's reading of this traditional ballad restores the older female-narrator version of the song, in which a woman looks…
ruin and regret intergenerational warning fatalism
Lead Belly
Lead Belly's version of the traditional ballad frames the ruinous house not as a place the singer escapes but one he's…
ruin and regret fatalism warning across generations
Mott the Hoople
This is Mott the Hoople's own epitaph and origin story rolled into one, a self-mythologizing autobiography written at the exact…
rock stardom as self-destruction nostalgia and regret band identity and mythology
Eurythmics
A withering breakup address in which the speaker refuses to justify the end of a relationship, cataloguing the addressee's…
emotional exhaustion refusal of explanation wasted time and regret
George Jones builds this song around a striking conceit: the truth itself shows up as a character, confronting a man about the…
personified truth/conscience infidelity and self-deception moral reckoning
Gladys Knight
A slow, torch-song lament about loving someone who no longer returns the feeling, sung with the weary authority of a performer…
unrequited love emotional entrapment regret and self-knowledge
The Cure
A grief-drenched meditation on a lost relationship, told entirely through the act of staring at photographs and the memories…
grief and loss memory versus reality obsessive love