The 50 Saddest Songs of All Time

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10. Roy Orbison – “Crying”
Of all the indelible classics that Roy Orbison graced us with before shuffling off this mortal coil in 1988, none feel more permanently etched into the shale of our collective psyche than this gorgeous heartbreaker that he released in 1961. Its power resides in its slowly stately build up with shuffling drums, a sly bit of marimba, and those weightless strings wafting through it all. Stranded in the middle of this musical swirl stands Orbison, bleeding with emotion as he recounts all the reasons that his shattered heart is never going to heal and his tear-stained cheeks will never dry. Just singing about it stirs it all back up again so by the song’s end, he’s almost wailing. Almost.—Robert Ham

9. Etta James – “All I Could Do Was Cry”
Weddings are generally happy occasions—unless your true love is getting hitched to someone else. It’s one thing to see your man out with another woman; it’s quite another to see him pledge his life to her. That’s the pain that Etta James sings about, and all the woe and ache in the world is carried by that ranging, soulful voice. “For them life has just begun / But mine is at an end,” she sings. This is a song that more people should know, but that no one else should ever attempt to cover.—Josh Jackson

8. R.E.M. – “Everybody Hurts”
“Everybody Hurts” is one of the rare songs on this list that actually offers catharsis. It’s beautifully simple: you’re sad, but you’re not alone because “everybody hurts, everybody cries.” You’re human, in other words, and we all have our moments. So take R.E.M.’s advice, “take comfort in your friends,” blast this song, have yourself a good cry, and then move on. You’ll feel better, I promise.—Bonnie Stiernberg

7. Jeff Buckley – “Hallelujah”
Leonard Cohen  wrote more than 80 verses to “Hallelujah” before paring down the epic song for release on the album Various Positions in 1984. But it wasn’t until the song was covered by Jeff Buckley 20 years later that it became the sad, desperate lament that would slowly find its way into children’s movies, presidential TV shows and everywhere else. The song has now been covered by more than 300 recording artists all over the world, but Buckley’s version remains the high-water mark, a cold and broken Hallelujah best listened alone in the dark with the volume turned way up. Cohen has a way of invoking deep spiritual longing with Biblical references that turn extremely personal, and Buckley had a way of drenching it all in tremulous emotion. The combination is transcendent.—Josh Jackson

6. George Jones – “He Stopped Loving Her Today”
A couple facts to consider here: few genres consistently produce sad songs that’ll punch you right in the heart quite like country does. Few country artists have the talent and inherent pathos to deliver these sad songs quite like George Jones did (see also: “If Drinking Don’t Kill Me, Her Memory Will”), and no George Jones song can consistently make cowboys and non-cowboys alike cry into their beer quite like “He Stopped Loving Her Today.” It’s a tragic tale of devotion (spoiler alert: he stopped loving her because he’s dead) and unrequited love, and if it doesn’t give you a lump in your throat, you should probably get your pulse checked just to be safe.—Bonnie Stiernberg

5. Dolly Parton – “Jolene”
Who could write a better song to “the other woman” than the Queen of Country herself? “Jolene” is a good example of a sad song that doesn’t exactly sound sad but doesn’t need to in order to convey the narrator’s desperation. With each pleading, “Jole-e-e-ne!” Parton plays the completely helpless partner, resorting to literally begging the haunting addressee not to steal her lover.—Tess Duncan

4. The Magnetic Fields – “I Don’t Believe In The Sun”
Leave it to the man who released 69 Love Songs to out-sad every other modern ode to heartbreak. With his deep, hang-dog voice, Stephen Merritt can no longer imagine that the sun would even bother to shine on a world where his love is gone. “How could there be such cruelty?” On an album that addresses the concept of love from just about every angle, it’s a song about its absence that reminds us all what’s at stake.—Josh Jackson

3. Johnny Cash – “Hurt”
Country icon Johnny Cash released his final album, the covers-heavy American IV: The Man Comes Around, in November 2002. His wife, June Carter Cash, died six months later—followed four months after by Cash himself. It’s hard to separate the album from its contextual sadness—especially given the LP’s heart-stopping centerpiece, a brooding rendition of Nine Inch Nails’ “Hurt,” in which the iconic singer glimpses his own mortality. “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. “What have I become, my sweetest friend?/ Everyone I know goes away in the end.” Trent Reznor’s dissonant original—recorded for the second NIN album, 1994’s The Downward Spiral—is often interpreted as a suicide note. In Cash’s hands, it’s a death-bed confessional.—Ryan Reed

2. Hank Williams – “I’m So Lonesome I Could Cry”
The sorrow behind this Hank Williams classic is heightened by the way each grief-stricken element of the song comes together. The robin, the whippoorwill, the midnight train—they all mourn with him to meet his quavering drawl, the imagery paralleling the sonic atmosphere. Jerry Byrd’s clever steel guitar flourishes are nestled snugly between verses until the drama of Tommy Jackson’s whimpering fiddle swoops in. 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

1. Sufjan Stevens – “Casimir Pulaski Day”
There is one moment in one song in the world that gives me chills every time I hear it. When the narrator looks at the body of the girl he loves after she finally succumbs to cancer, he thinks for a moment that he sees her breathing. Then he sings about God: “All the glory when he took our place / But he took my shoulders and he shook my face / and he takes and he takes and he takes.” He’s trying to reconcile the generosity of Jesus allowing himself to be sacrificed on the cross with a god who would let a young girl die from leukemia. And the only conclusion is a chorus of angels whose weeping turns into something like joy as a triumphant trumpet kicks in. There are so many details that lead to my inevitable goosebumps: the guilty sexual explorations of teens who’ve been taught the importance of abstinence (“I almost touched your blouse”); the strict and distant father who makes a big display of his grief; the ineffectual laying of hands and praying; the cardinal hitting the window. Because the characters seem so real, so does the sorrow. I feel deeply for the dying girl and the boy who can’t understand the Why of it all—because none of us really can.—Josh Jackson

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