old sad songs

She sums up those natural feelings of jealousy when an ex moves on to someone new sooner than expected. A brief summary of its events: a teen couple in a dead-end town accidentally get pregnant. Bringing her mundane routine to life, Griffin’s song drips with the melancholy of a woman who’s accepted her fate (“I used to mind, but I don’t care ’cause I’m gray”) but can’t stop thinking of what might have been. The sorrow behind this Hank Williams classic is heightened by the way... 3.

Laura Viers – “Sadako Folding Cranes”, 14. In This Article: Sign up for our newsletter. Another man-fighting-with-his-wife country ballad is deceptive as the chorus swells up “You don’t know sadness til you face life alone / You don’t know about lonely ’til it’s chiseled in stone…” Suddenly, sorrow’s permanence is concrete, pride is poison and Vern Gosdin bends notes and your heart. There are few things in life as tragic as dead kids, and sadly, “Little Bonnie never married, Little Bonnie never even made it four.”—Bonnie Stiernberg, When Beck released Sea Change in 2002, gone were his freeform experimentations in the jigsaw jazz and get fresh flow. “I hurt myself today/ to see if I still feel,” Cash sings over wispy acoustic guitar and piano chords, his ancient baritone quivering in the darkness.

It’s 1989’s Country Music Association’s Song of the Year for good reason.—Holly Gleason, I was trying to keep this list to one song per artist and almost included Lefty Frizzell’s original version of the song, but Cash’s is just more potent. “Angels Rejoiced,” indeed.

by the admonishing acoustic cut “Lost Cause,” a hallucinatory goodbye letter to an unknown lover, Beck’s repeated refrain of “I’m tired of fighting” sounds as eerily comforting today as it did over a decade ago.—Ryan J. Prado, This 1982 Tears For Fears song achieved another round of fame when Gary Jules and Michael Andrews covered it for the Donnie Darko soundtrack in 2001. The track’s massive sound contributes to the punch it packs—as the strings swell and fall, the brooding piano chords mingle with Winehouse’s grief-stricken vocals and pauses are filled in by spare tambourine shakes. Here, Beam has accomplished nothing less than telling the story of our sadness.—Shane Ryan, Heartbreak and whiskey-drinking is standard fare for country songs, but “Whiskey Lullaby” has a distinctly more melancholy tone. From the time I arrived, I could tell she was over our relationship. And the only conclusion is a chorus of angels whose weeping turns into something like joy as a triumphant trumpet kicks in.

Vic Chesnutt – “Flirted With You All My Life”, 41.

She begs him to repent. And suffer just enough to sing the blues. Williams originally intended the lyrics to be spoken rather than sung, which would have been a crime when you consider how gutting it is to hear his voice sway and crack through, “And as I wonder where you are/ I’m so lonesome I could cry.”—Tess Duncan, There is one moment in one song in the world that gives me chills every time I hear it. Like most great songs, the lyrics alone don’t tell the story, but the simple refrain gets at the heart of the temporary nature of our lives contrasting with our human urge for permanence: “Please remember me.” Beam’s voice is at its most nostalgic here, and he tells the story of a boy and girl who connected and blew apart, complete with circus imagery, snippets of memory, and the bright, painful moments of consummation and separation. So I can relate to Ben Gibbard’s narrator in “The District Sleeps Alone Tonight.” He probably had such high hopes his time in D.C., but it’s just left him unwanted and unloved and a little disoriented in a strange place where he clearly doesn’t belong.

If your favorite is missing, add it to the comments section below. The song’s narrative ranges from heaven to hell, and represents Beam’s most ambitious poetry—it’s long, it meanders, and it hits you with a desperate intensity. The combination is transcendent.—Josh Jackson, A couple facts to consider here: few genres consistently produce sad songs that’ll punch you right in the heart quite like country does.

In short, it’s the Smithiest of Smiths songs.—Josh Jackson, We could easily pull out half a dozen Elliott Smith songs for this list, and nearly that many were nominated. Within the narrative, “Mad World” builds a universe of nameless faces in common situations, from birthday parties to school classes.

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