The 50 Saddest Songs of All Time

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The 50 Saddest Songs of All Time

If misery loves company, sometimes there’s no better friend than a really good, really sad song. It assures you that you’re not alone, that someone else has felt this pain and turned it into a gift for you. Locking yourself in your bedroom to listen to mopey music isn’t just wallowing. It’s allowing the grief a place to breathe, allowing you to experience the pain in its fullness and hopefully come out the other side. We need sad songs for the comfort they can provide. Bernie Taupin captured this sentiment best and hid it in a jaunty little pop song by Elton John:

If someone is suffering enough to write it down
When every single word makes sense
Then it’s easier to have those songs around
The kick inside is in the line that finally gets to you
And it feels so good to hurt so bad
And suffer just enough to sing the blues

Yes, sad songs do say so much. And these 50 songs helped the Paste staff to hurt so good. I tried to keep it to one song per artist but Johnny Cash ended up getting a pass. This list barely scratches the surface of sad songs—or even sad songs that got nominated by our writers. If your favorite is missing, add it to the comments section below. Here are our 50 favorite of the saddest songs:

50. Angel Olsen – “Windows”
This is a sad song with a secretly positive message. “Windows” is wistful but more for its instrumental composition and Olsen’s gossamer vocals. Just a few soft riffs and gentle drum hits are all that’s needed to back the wavering twang in her voice as she encourages a friend to move on from their dark past. Though it sounds like she’s singing through trembling lips, Olsen’s spirit is uplifting. There are loads of upbeat songs with depressing lyrics but “Windows” does the opposite, inducing tears despite its bright imagery.—Tess Duncan

49. Tammy Wynette – “D-I-V-O-R-C-E”
The undulating pedal steel guitar on “D-I-V-O-R-C-E” pulls at metaphorical heartstrings, but the lyrical content is gut-wrenching enough on its own. Tammy Wynette articulates the internal struggle of so many divorcees-to-be with children, the strain and ache in her warble serving as a vehicle for her overwhelming remorse. Plus juxtaposing words like “toy” and “surprise” with “divorce” and “custody” severely ups the misery factor.—Tess Duncan

48. Delta Spirit – “Vivian”
Matt Vasquez wrote this History From Below tearjerker as an ode to his late grandparents, who both passed away within a short timeframe. It’s written from the perspective of his deceased grandfather, who implores his still-living wife to “sleep oh sleep, my Vivian” because “heaven is too cold without you.” I mean, come on. If your heart is made of stone and that’s not enough to choke you up, he also visits his ailing wife from beyond the grave to comfort her as she dies: “I know it’s hard to deal with the pain/you’re yellow from your liver giving out/so just close your eyes and think of me/oh, Jerry’s not leaving this gal.” I’m getting misty just thinking about it.—Bonnie Stiernberg

47. Shelby Lynne – “Heaven’s Only Days Down the Road”
Written a quarter century after her father shot and killed her mother then himself in the driveway of their home in Monroeville, Alabama, the hurt still feels fresh for singer/songwriter Shelby Lynne. Sung from the perspective of her father a few days before his death (“I been insane since I was nine / Never was the cryin’ but the fightin’ kind / Load up the gun full of regret / I ain’t even pulled the trigger yet”), the driving blues rhythm feels frantic as we all know how the story ends. She and her sister Alison Moorer are the “two little girls better off this way,” orphaned at 17 and 13 and sent off to live with relatives.—Josh Jackson

46. Vic Chesnutt – “Flirted With You All My Life”
When it comes to sad songs, I can’t think of anything quite as powerful or heartbreaking as Vic Chesnutt’s “Flirted With You All My Life.” Chesnutt is a poignant figure in general—an Athens, Ga. legend who created wild, beautiful music until his death in 2009. But it’s through songs like this one that he transcends even that. “Flirted With You All My Life” is sobering, addressing death directly: “Oh death, oh death, oh death / Really, I’m not ready.” It relates his own experience with dying, whether through his lifelong flirtation with suicide or his mother’s battle with cancer, and it’s that honesty paired with Chesnutt’s colorful past that will make you question and almost certainly cry—in public, for the public or for life’s adventure in general.—Brittany Joyce

45. Perfume Genius – “Mr. Peterson”
Mike Hadreas’ songwriting is unabashedly raw, the kind that speaks about the dirty and the unsightly in a way you can’t ignore. He puts a traumatic experience into words that sound like poetry—they’re arranged in such a way that it’s almost just as heartbreaking to read them on paper as it is to hear Hadreas tenderly singing them. But it wouldn’t have quite the effect without that bleak, pulsating piano line.—Tess Duncan

44. Eric Clapton – “Tears in Heaven”
This Eric Clapton ballad has gotten a lot of play in the 20-plus years since its initial release, and you’d think that would dull its sadness a bit, but just take a minute and remind yourself of its tragic origins: Clapton’s four-year-old son Conor fell out of a 53rd-floor window and died in 1991, and “Tears in Heaven” is the songwriter’s attempt to express his grief, speculating whether his young child would even recognize or remember him in heaven.—Bonnie Stiernberg

43. Ben Folds Five – “Brick”
Ben Folds understandably struggled to write “Brick,” a song about his high school girlfriend’s abortion. With such a delicate experience on his hands, he admitted that the choruses he came up with sounded too literal. Luckily Darren Jessee provided the refrain, “She’s a brick and I’m drowning slowly/ off the coast and I’m headed nowhere” for Folds’ distressed falsetto. Carried by a somber piano melody and underscored by Jessee’s subdued drumming, it manages to sound serene in spite of the emotional turmoil behind each of Folds’ troublesome scenes.—Tess Duncan

42. Iron & Wine – “The Trapeze Swinger”
I still remember the exact spot where I first I heard “Trapeze Swinger,” which is pretty unusual for me—I have a decent memory for where I’ve read certain unforgettable books, but songs tend to blend in space and time, since you can listen to them over and over and gradually erase the point of origin. But “Trapeze Swinger” made such an unforgettable impression that the setting remains locked in my head—senior year, central campus apartment, sitting in front of my computer with AIM running, heartbroken. This song hit me at the perfect time in life, and seemed to capture a kind of ineffable melancholy that went beyond the girl I was pining over, and was instead an essential part of the human experience. 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. 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. Great art doesn’t necessarily tell you something new, but rather puts words to something you always knew, but couldn’t name. Here, Beam has accomplished nothing less than telling the story of our sadness.—Shane Ryan

41. Brad Paisley and Alison Krauss – “Whiskey Lullaby”
Heartbreak and whiskey-drinking is standard fare for country songs, but “Whiskey Lullaby” has a distinctly more melancholy tone. “She put him out like the burnin’ end of a midnight cigarette,” it begins, detailing the sorrow of a man drinking away memories until they kill him.” We found him with his face down in the pillow / with a note that said I’ll love her till I die,” it says, and the guilt of his demise leads his ex-lover to the same fate. The imagery alone is gripping, but the gentle harmonies from Krauss are what push this mournful track into sob-worthy territory.—Dacey Orr

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