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

40. XTC – “Dying”
XTC’s bassist and occasional songwriter Colin Moulding spent a lot of his compositional energy concerned with matters of getting old and passing away. For the most part, it’s a gentle obsession, as he assures himself in songs like “One of the Millions” and “Bungalow” that his sagging skin and greying hair are earned rather than thrust upon him. But on this song, found towards the end of XTC’s magisterial 1986 album Skylarking, Moulding lets all of his fears come right to the surface, spelling out in exacting detail the experience of watching a relative pass slowly away and not wanting to share that horrible fate. The music, for the most part, hangs back from his resigned vocals, clicking away like a bit of hospital machinery and only interrupted by a haunting piano roll and a fluttering bit of melodica.—Robert Ham

39. Robyn – “Dancing on My Own”
It’s probably safe to assume that Robyn advocates dancing your worries away, so it makes sense that she’d write a song that’s empowering in its self-awareness. She sums up those natural feelings of jealousy when an ex moves on to someone new sooner than expected. But instead of writing a dreary ballad about it, Robyn flipped the script. Though she’s watching her former love get frisky with his “new friend” in the club, the chorus doesn’t come across as self-pitying. Instead she triumphantly announces, “I keep dancing on my own.” The situation is undeniably hurtful and uncomfortable, but Robyn wants her audience to know that she’s going to be just fine alone, and you are too.—Tess Duncan

38. The Postal Service – “The District Sleeps Alone Tonight”
After one particular summer romance, I visited my girlfriend at her college two hours away, and the trip went horribly. From the time I arrived, I could tell she was over our relationship. 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. That feeling he’s having, I can personally attest to its level of suckiness.—Josh Jackson

37. Sun Kil Moon – “Carissa”
Benji is an album heavily focused on death. Of all the tragedies on the record, “Carissa” is the most gruesome and harrowing. Over some sparse, rumbling guitar plucks, Mark Kozelek memorializes Carissa, a mother who died in a fire at the age of 35. It’s a disturbing story made only more dismal when backing vocalists harmonize with Kozelek on lines like, “Carissa was 35/ You don’t just raise two kids and take out your trash and die.”—Tess Duncan

36. Tom Waits – “Anywhere I Lay My Head”
The moaning organ provides a steady accompaniment for Tom Waits’ gruff wailing on this desolate blues song. He delivers with anxiety-driven urgency, sounding like he could just break down into a blubbering frenzy at any moment. The horn section rides along smoothly in comparison, cresting and dipping deftly as Waits sings vigorously, wounds exposed. There’s no one who can pull off the palpable dejection of “I don’t need anybody, ’cause I learned to be alone” quite like Waits does.—Tess Duncan

35. The Smiths – “There Is a Light That Never Goes Out”
Oh, how to pick just one Smiths song for this list? Well, the most joyful moment of “There Is a Light That Never Goes Out” is when the narrator daydreams about a 10-ton-truck crashing into his car. Feeling unloved at home, he wants to escape with the one he loves, but he’s too scared to do anything about that love. Meanwhile, the keyboard line bounces happily along. In short, it’s the Smithiest of Smiths songs.—Josh Jackson

34. Elliott Smith – “Fond Farewell”
We could easily pull out half a dozen Elliott Smith songs for this list, and nearly that many were nominated. But when “Fond Farewell” was released almost a year to the day after his apparent suicide, this was the song that wrecked me. Smith wrestled his demons in his music, and “Fond Farewell” feels like his goodbye note in song. It’s filled with regret for the way things went. When he sings, “a fond farewell to a friend who couldn’t get things right,” it leaves you with a feeling of helplessness, wishing he were still here. That the words are set to his impossibly lovely melodies just makes it harder to hear.—Josh Jackson

33. Patty Griffin – “Making Pies”
A great song can help you see the world from a different perspective, as Patty Griffin often proves. The subject of “Making Pies” is a lonely spinster whose sweetheart died in the War. 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. “You could cry or die or just make pies all day,” she sings at the song’s conclusion. “I’m making pies.”—Josh Jackson

32. The Louvin Brothers – “The Angels Rejoiced Last Night”
“A house not a home is a picture Satan painted / for dear little sister ’n’ me,” opens the Louvin Brothers’ twisting, minor-key lament of a family near destitution from a no-good man’s high-timing. Mother prays. Father gambles, drinks, runs around. She begs him to repent. He refuses. Things get worse. Mother gets sick, prays, dies. Finally, father gets religion. Too late to ease his wife’s pain, shame or struggle. “Angels Rejoiced,” indeed. With their Appalachian twin harmony, it is the sorrow of the mountains distilled.—Holly Gleason

31. The Mountain Goats – “No Children”
This song leans a little harder on the angsty side of things, but it’s a lament-filled breakup song nonetheless. John Darnielle spends most of the song wishing ill upon his ex-lover, but it’s made even more severe by his wishes of suffering for himself. Winner for most upsetting lyric is hands-down: “I am drowning, there is no sign of land/ You are coming down with me, hand in unlovable hand/ And I hope you die, I hope we both die.” Darnielle’s sheer despondency and lack of any hope for a better tomorrow is what makes this track so disheartening.—Tess Duncan

30. Pearl Jam – “Last Kiss”
Pearl Jam’s cover of the 1960s teenage tragedy song “Last Kiss” is heart-wrenching both because of its lyrics and Vedder’s performance. His warbling voice is perfect for the tone of the song—it’s not hard to believe that he’s heartbroken over the loss of his young love. Two teenagers are out on a date when they get into a terrible car accident and the narrator’s girlfriend dies in his arms. He begins with hope that if he lives a good life he’ll eventually see her in Heaven, but as he relives the events of the night that took her, he falls into despair. Both the lyrics and the music are simple, but its repetitive rhythm, steady beat and basic rhyme scheme just make it more relatable. In the second verse—”Something warm flowing through my eyes / But somehow I found my baby that night / I lifted her head, she looked at me and said / ‘Hold me darling just a little while’”—Vedder’s voice cracks on the final line, as the dying girl begs her boyfriend to hold her while she slips away. Vedder sings the final chorus with renewed agony and then hums a hymnal-like, wordless tune before the instruments and Vedder both fade into silence. “Last Kiss” captures pain and grief and wraps in a simple pop beat that’s hard to forget.—Danielle Ryan

29. Sinead O’Conner – “Nothing Compares 2 U”
As soon as Sinead O’Connor kicks things off with that mournful “it’s been seven hours and 15 days since you took your love away,” it’s not easy to refrain from picturing the iconic music video that accompanied this, the ultimate break-up song. That close shot of O’Connor’s face with the tears rolling down it will forever be etched into our memories, but there’s a second layer of sadness to “Nothing Compares 2 U.” Those are real tears O’Connor shed in the video, and she has stated that they were triggered by thoughts of her recently deceased mother thanks to the line “all the flowers that you planted, mama / in the backyard / all died when you went away.”—Bonnie Stiernberg

28. Justin Townes Earle – “Yuma”
Justin Townes Earle named his 2007 debut EP for this searing, solo-acoustic suicide song. Over his claw-hammer finger picking, Earle lists a litany of afflictions—poverty, alcoholism, loneliness, klutziness, and lost youth and love—throughout a third person narrative. But in the bridge, Earle shifts the perspective to that of the omniscient narrator. He surmises in first person, “Lookin’ back I’d say it wasn’t so much the girl / as it was the booze and the dope and the way he took the weight of the world up upon his shoulders.” It’s this masterful balance of attention to detail—from naming the girl who broke his heart to describing the car that caught the weight of his jumper—and empathetic universality that makes so “Yuma” so fictionally affective, but realistically relatable.—Hilary Saunders

27. Sarah McLachlan – “When She Loved Me”
Everyone always talks about how Toy Story 3 destroyed them emotionally (and it did for me too), but the Toy Story scene that consistently breaks me up is the one from Toy Story 2 when Sarah McLachlan sings this Randy Newman song about a toy getting abandoned by her owner as she grows up. I’m not a big Disney/Pixar person, but I have a distinct memory of seeing the movie in theaters with my parents as a kid, looking over during this scene and noticing that even my dad was crying. Over a cartoon toy cowgirl getting left under a bed. And if that’s not brutal enough, the song fakes you out, filling you with false hope that its narrator will be loved again before revealing that her now-grown owner only picked her up to PUT HER IN A CARDBOARD BOX AND LEAVE HER ON THE SIDE OF THE ROAD. UGH, THE PASSAGE OF TIME. GETS ME RIGHT IN THE HEART.—Bonnie Stiernberg

26. Glen Campbell – “I’m Not Gonna Miss You”
At the beginning of 2011, Glen Campbell was diagnosed with Alzheimer’s disease. After a final tour the following year, the Grammy-winning country singer, TV host and actor recorded a farewell song for a the documentary Glen Campbell: I’ll Be Me, even as he could feel his mind slipping. The father of eight children from four wives, Campbell has been married to Kim Woolen for more than three decades. It’s to her that he addresses the painful refrain over and over in the song. “I’m never gonna hold you like I did / Or say I love you to the kids / You’re never gonna see it in my eyes / It’s not gonna hurt me when you cry / I’m not gonna miss you.” Knowing that Campbell was lucid enough to co-write and perform the song, feeling the truth of every word, and probably no longer is, is heartbreaking.—Josh Jackson

25. Bruce Springsteen – “The River”
Bruce Springsteen’s “The River” isn’t just sad—it’s absolutely soul-crushing. A brief summary of its events: a teen couple in a dead-end town accidentally get pregnant. There’s a shotgun wedding, and Bruce does all he can to remind us no one’s exactly psyched to be getting hitched (“for my 19th birthday I got a union card and a wedding coat” ... “no wedding-day smiles, no walk down the aisle, no flowers no wedding dress”). The narrator works construction, but there’s no work because the economy is terrible. Their relationship is a shell of what it once was, and memories of their early sparks “come back to haunt me, they haunt me like a curse.” And if that’s not enough, it also contains one of the biggest bummers of a line ever: “Is a dream a lie if it don’t come true, or is it something worse?”—Bonnie Stiernberg

24. Camper Van Beethoven – “All Her Favorite Fruit”
The desperate loneliness the narrator feels comes through in nearly every line of David Lowery’s lyrics, as he dreams of a girl out of his league. Sure there’s a bit of creepiness on the part of a guy who calls the object of his affection and never says a word, just imagining what she looks like on the other end of the line—especially since she already has a man in her life. All he can do is ride the train to an unfulfilling job and dream of all the places he wants to take her. Chris Pederson’s thumping tom drums measure out the mundane days while Don Lax’s violin counters the pitiful longing with a beautiful melancholy. You don’t have to dream of playing croquet or drinking your tea at four to feel the pain of unrequited love.—Josh Jackson

23. Townes Van Zandt – “Waiting Around to Die”
Stark. The echo chamber of a broken heart for a beat; dried twigs scratching at a cold window for a voice make Townes Van Zandt’s “Waitin’ Around To Die” a haunting more than a song. Beaten women, getting hustled, crime gone bad, jail time, addiction. Two minutes, 23 seconds of harsh reality, stoic in its acceptance of a fate worse than death.—Holly Gleason

22. Amy Winehouse – “Back to Black”
There’s never been a shortage of soulfulness in Winehouse’s songs, so it’s no surprise that she crafted such a painful breakup song. “Back to Black” recalls ’60s doo-wop with a moody, creeping tempo. 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. Not many songs can sum up being dumped for an ex as well as Winehouse does when she woefully sings, “I died a hundred times.”—Tess Duncan

21. Neutral Milk Hotel – “Two Headed Boy Pt. 2”
It’s difficult to talk about “Two-Headed Boy Pt. 2” without talking about the album it brings to a powerful close, but I do believe that even without the context of In the Aeroplane Over the Sea, the song stands out as one of the most moving pieces of music in the past two decades. Like most of Jeff Mangum’s work, there are times when you have to put in some effort to parse the expressionistic imagery (“blister please with those wings in your spine…how he’d love to find your tongue in his teeth”) but at other times, the emotion is plain and jarring. “In my dreams you’re alive,” he sings, in that plaintive, keening, inimitable voice, and it builds to a climax that I, personally, find devastating: “When we break, we’ll wait for our miracle. God is a place you will wait for the rest of your life.” I can’t think of a better way to encapsulate the hope and fear and agony and grace of being alive. Nor can I think of anyone who can somehow express this inexpressible concept with such power and emotional precision quite like Mangum. At the song’s end, you can hear the scuffling sound of a chair as he rises and leaves—a subtle, poignant conclusion to one of the most singular, beautiful albums ever made.—Shane Ryan

20. Laura Viers – “Sadako Folding Cranes”
When your topic is the atom bombing of Hiroshima, the resulting tune isn’t going to end up in your “happiest songs” list. This track off singer/songwriter Laura Veirs’ most recent 2013 album Warp and Weft is a tribute to Sadako Sasaki, a Japanese child who lived about a mile from the epicenter of the Hiroshima blast, and was 2 years old when the bomb fell. Despite being literally blown through a window by the blast, Sadako appeared to be relatively unharmed and lived a normal childhood until she developed leukemia at the age of 11 from the lingering radiation. Confined to a hospital and slowly dying, she was told the Japanese legend of the “1000 origami cranes,” whose creator would supposedly be granted a wish. In her dying days, Sadako therefore worked on folding her own 1,000 cranes, but passed away having only completed 644. The remaining cranes were finished by friends and family, and the poor young victim of WWII was ultimately buried with them. The whole story is recounted in much more detail in a work of historical children’s fiction by Eleanor Coerr, Sadako and the Thousand Paper CranesJim Vorel

19. Drive-By Truckers – “Little Bonnie”
Look, when your name is Bonnie, a song about a dead girl called “Little Bonnie” is going to make you sad. When your dad still calls you “Little Bonnie” sometimes even though you’re a few months shy of 27 and the song kicks off with the line “On the day that she was buried/Her Daddy stood out by the cemetery fence/Prayed to God for forgiveness/For surely all of this is punishment for my sins,” it’s pretty much tailor-made to make your heart ache. But you don’t have to be a Bonnie—little or big or in-between—to be moved by this Drive-By Truckers track. 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

18. Beck – “Lost Cause”
When Beck released Sea Change in 2002, gone were his freeform experimentations in the jigsaw jazz and get fresh flow. In its place was one of the most depressing-sounding—and artistically brilliant—albums in recent memory. Highlighted (lowlighted?) 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

17. Gary Jules – “Mad World”
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. Jules and Andrews traded the original pulsating synths for a stark, arpeggiated piano line and soft mellotron swells that arguable better emphasize the brooding lyrics of alienation. Within the narrative, “Mad World” builds a universe of nameless faces in common situations, from birthday parties to school classes. But in the chorus, Jules manages to laugh in spite of his dreams of death. It’s the ultimate mockery to compensate for (and attempt to comprehend) our irrevocable finality.—Hilary Saunders

16. Vern Gosdin – “Chiseled in Stone”
That molten caramel voice drenches an acoustic guitar. 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. It’s 1989’s Country Music Association’s Song of the Year for good reason.—Holly Gleason

15. Johnny Cash – “Long Black Veil”
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. Written by Marijohn Wilkin and Danny Dill in 1959, the song tells the tale of a man wrongfully hanged for a murder because his alibi happens to be married to his best friend. Rather than betray his love and ruin a marriage, he carries the secret to his grave, leaving his lover in a state of constant mourning.—Josh Jackson

14. The Velvet Underground – “Pale Blue Eyes”
A hauntingly beautiful tale of unrequited love, “Pale Blue Eyes” is about recognizing you’re being used and allowing it to happen anyway. It’s one of the few songs that can make the phrase “best friend” feel as cutting as a four-letter word, as Lou Reed sings “It was good what we did yesterday, and I’d do it once again. The fact that you are married only proves you’re my best friend.” Anyone who has ever been friend-zoned can relate to the aching sadness oozing from this track.—Bonnie Stiernberg

13. Joy Division – “Love Will Tear Us Apart”
There’s no misery quite like seeing the ashes of what was once love’s burning fire. Ian Curtis captures that despair on Joy Division’s most recognizable song. A relationship full of resentment, as the bedroom has turned cold and all his failings have been exposed, is something to mourn, and everything about this song super-charges that mopey feeling. There’s nothing more empty than the space where love used to be. —Josh Jackson

12. Aretha Franklin – “Ain’t No Way”
Songs about unrequited love are inherently sad, but “Ain’t No Way” is one of those rare melancholy masterpieces that makes you want to nod knowingly in support and raise your hands in silent agreement while Aretha testifies. To say she sings her heart out on this song would be trite and also a gross understatement—she turns in a wailing vocal performance so good that she manages to overpower Cissy Houston’s otherworldly backup “ooooOOOOOOOOOO”s and make you forget where you are as the horns swell and her pleas to the man who won’t love her back grow more and more desperate. It’s sad, yes, but it’s also life-affirming that there are still people out there like Aretha loving this deeply—whether the feelings are reciprocated or not.—Bonnie Stiernberg

11. Harry Chapin – “Cat’s In The Cradle”
“Cat’s in the Cradle” is a song so sad that it’s become shorthand for the idea of sad, manipulative songs, to the point that it’s practically a punchline—you couldn’t help but laugh when it popped up so guilelessly in a Nissan commercial in this year’s Super Bowl, reinforcing the odd theme of “sad fatherhood” ads running that evening. It preys on the guilt of every career-dedicated parent—first you don’t have any time to spend with the kids because you’re always working, and then they grow up and don’t want to spend any time with YOU. “How did we drift apart?” the parent presumably asks, only to be told by the kid, “I learned it from watching YOU, Dad!” It’s a song that will put tears in the eyes of many parents, but in reality you could use practically any Harry Chapin song for this kind of list, as depressing stories were really the guy’s true medium. There’s the song about the band on the Titanic, playing as the ship sinks. Or the song from the perspective of a crooked cop trying to hide his kickback money from his young son to not lose his respect. Or the song about the evil small-town mayor who tricks his illegitimate son into hooking up with his half-sister. THESE ARE ALL REAL. Harry Chapin is not kind to the characters in his songs.—Jim Vorel

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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