The 25 best sad songs ever written

Sometimes, a bad day calls for a shoulder to cry on. Others call for a stiff drink. And some days, you just need to throw on your headphones, crank up the volume and wallow in your own sorrow to the soundtrack of an emotionally devastating song that seems written exclusively for you. 

Sad songs come in all flavors, from breakup anthems to 12-bar blues. But if you’re just looking for a soundtrack calibrated to general malaise, this list is for you. And don’t worry… once you’re done (or just out of ice cream), we’ve got a stack of extremely happy songs to get you back on your feet. 

"Nothing Compares 2 U" by Sinéad O’Connor

Image: Ensign

1. “Nothing Compares 2 U” by Sinéad O’Connor

The original version of “Nothing Compares 2 U,” tossed off by Prince in the mid-’80s and released by the purple one’s protégés The Family, is a straight-up (and pretty forgettable) break-up song. But O’Connor’s version dialled the sad factor to 11, channeling the singer’s very real grief from the death of her mother five years previously. A superb vocal performance – the sound of naked sorrow – plus layers of weeping synth strings and an iconic, tear-streaked music video added up to one of the most successful sad songs in musical history. Pop music doesn’t get much closer to the bone.

"Hurt" by Johnny Cash

Image: Universal

2. “Hurt” by Johnny Cash

On paper the idea of a country music legend covering Nine Inch Nails sounds absolutely ghastly – even Trent Reznor thought so. But “Hurt” was Johnny Cash’s final triumph, recorded less than a year before his death. Bad health had worn down Cash’s scowling baritone, but the cracks in his voice helped the Man in Black turn Reznor’s petulant angstfest into his own all-American epitaph. The video ramped up the heartache: shots of the frail but dignified Cash were intercut with shots of his wife June, footage of his past glories and pictures of the crumbling, derelict House of Cash museum in Tennessee. “Hurt” is a man singing in the face of death, channelling a lifetime of memory, pain, hard-won success and thwarted ambition.

"Only Love Can Break Your Heart’ by Neil Young

Image: Reprise

3. “Only Love Can Break Your Heart’ by Neil Young

Yes, dance-pop troupe Saint Etienne made a jauntier version in 1991, and yes, it kind of overshadowed the enigmatic Canadian songwriter’s 1970 original. But it shouldn’t have. Young’s beaten-down folky ballad is the sound of someone resigned not just to momentary heartbreak but to a lifetime of sadness – yet somehow there’s still a hint of a ghostly, golden melody in there. It’s also been covered by Natalie Imbruglia, The Corrs, Psychic TV and Jackie De Shannon, to name a few from a very long list. Apparently misery is something that a lot of people relate to. Who knew?

"Teardrop" by Massive Attack

Image: Virgin Records

4. “Teardrop” by Massive Attack

Trip hop provided the tasteful music fan’s weepy soundtrack of choice for much of the ’90s, with tracks like Portishead’s “Roads” inspiring plenty of late-night bedroom sob-alongs. “Teardrop” stands above the pack — despite a plague of horrendous cover versions and a weird afterlife as the title song for House — because of the haunting vocals by Elizabeth Fraser of Cocteau Twins. The song became deeply personal for her when, on the day of recording, she heard that her ex-lover Jeff Buckley had drowned in Memphis.

"I Know It’s Over" by The Smiths

Image: Rough Trade

5. “I Know It’s Over” by The Smiths

Morrissey hates being pigeonholed as miserable, but he really did bring it upon himself sometimes. In the ’80s and in cahoots with Johnny Marr he contributed a whole series of wry studies in gloom and pain to the canon. “I Know It’s Over” may be The Smiths’ deepest journey into despair, with only the subtlest black humour (“I know it’s over… and it never really began”) to light the way. By the time we get to the relentless questioning at the centre of the song – “If you’re so clever/Then why are you on your own tonight?” – we are naked in front of the mirror with no-one to blame for our sorrow but ourselves.

"No Distance Left to Run" by Blur

Image: Food Records

6. “No Distance Left to Run” by Blur

Damon Albarn was locked in to sensitive mode for this one, stripping away all the beery bravado for a long and hard look at the end of his relationship with Justine Frischmann. With a melody like a lullaby and a title lyric that keeps coming back like a mantra, Blur’s “No Distance…” is an acceptance of sorts. But though the relationship is spent, the regret and resentment in the voice and the lyrics lets us know there’s more pain further down the road.

 "The Boxer" by Simon & Garfunkel

Image: Columbia

7.  “The Boxer” by Simon & Garfunkel

In which Paul Simon condenses the Great American Novel into a folk song. The central story’s a familiar one — Dick Whittington finds out the streets of NYC aren’t paved with gold after all — but the Arthur Miller-worthy final image of the unbowed boxer, and the string-swelling two-minute coda make it hit home with devastating force.

"No Name #5" by Elliott Smith

Image: Kill Rock Stars

8. “No Name #5” by Elliott Smith

Like a handful of other singers on this list, Elliott Smith passed away tragically young. His death in 2003 from two stab wounds (probably self-inflicted) cast a shadow over the five albums he had released, including 1997’s Either/Or, the record which included the last and greatest part of the ‘No Name’ song series that he’d started on Roman Candle in 1994. If there’s any couplet from Smith’s catalogue that that sums up the tension, lethargy and loneliness of depression, it’s here: “Got bitten fingernails and a head full of the past/And everybody’s gone at last.”

"Tom Traubert’s Blues (Four Sheets to the Wind in Copenhagen)" by Tom Waits

Image: Asylum Records

9. “Tom Traubert’s Blues (Four Sheets to the Wind in Copenhagen)” by Tom Waits

With his numerous gravel-voiced tales of whisky-sodden debauchery, it’s easy to forget that Tom Waits is something of a master at heart-piercing melancholia – never more so than on the opening track to 1976’s Small Change album. From the impossibly sad sweeping strings that introduce the song, you know this is going to be a dark one. There are various theories as to what and who the song is about, but as Waits growls through weird stories of alcoholic nocturnal street roaming, it hardly matters. When he brokenly cries, “I begged you to stab me, you tore my shirt open, and I’m down on my knees,” it’s impossible not to believe that it’s coming from someone who’s tumbled far lower than most ever will.

"Lazarus" by David Bowie

Image: Columbia

10. “Lazarus” by David Bowie

Bowie’s final album often plays like a self-written obituary, and it breakout single’ haunting horn jabs and slow tempo suggest a death march. “Look up here, I’m in heaven,” he entones on the eerie track released less than a month before his untimely death. One more melancholoc masterpiece from the Thin White Duke. Recommende

"Strange Fruit" by Billie Holiday

Image: Sonet

11. “Strange Fruit” by Billie Holiday

Though she’s also remembered for her version of the harrowing “Gloomy Sunday” (AKA “The Hungarian Suicide Song”), the incredible Ms Holiday left an indelible mark on the culture with “Strange Fruit.” Abel Meeropol’s horrific poem about lynchings in the southern states became the most powerful protest song of the twentieth century thanks to Holiday’s interpretation: understated, tense and as full of sorrow and humanity as righteous rage.

"The River" by Bruce Springsteen

Image: Columbia

12. “The River” by Bruce Springsteen

At his most bleakly empathetic, The Boss has more in common with the great American tragedians Arthur Miller and Eugene O’Neill than any of his songwriter peers. “The River’”is as devastating as it gets, a mournful account of two carefree young lovers forced into a joyless marriage after an unplanned pregnancy. “Is a dream a lie if it don’t come true, or is it something worse?” stands as one of great lines of the 20th century.

"How to Disappear Completely" by Radiohead

Image: Capitol Records

13. “How to Disappear Completely” by Radiohead

Anyone who thought in 1997 that Radiohead had reached the depths of bleakness with OK Computer got a big surprise three years later, when the band released Kid A and it turned out there were whole oceans of mumbling electronic melancholy they had yet to plumb. The acoustic strumming here is a throwback to the band’s Bends-era songwriting, but the unsettling synth drones, eerie lyrics and spine-chilling strings (recorded in Dorchester Abbey) sound like an audio document of Thom Yorke’s post–OK Computer mental breakdown.

"Neither One of Us" by Gladys Knight and the Pips

Image: Soul

14. “Neither One of Us” by Gladys Knight and the Pips

The soul legend deploys the Pips to devastating effect on this slow, methodical relationship post mortem in which Gladys examines an affair that simply wilted on the vine. Anyone who has ever come to the realization that their relationship cannot sustain solely on love will find a kindred spirit in Knight, whose final words — “farewell my love… goodbye” — are delivered with staggering finality that cuts to the bone.

"Someone Great" by LCD Soundsystem

Image: Capitol Records

15. “Someone Great” by LCD Soundsystem

It’s been said that the lost “someone” of this song was the psychiatrist Dr George Kamen – LCD main man James Murphy dedicated the band’s Sound of Silver album to him. Whoever the subject, the lyrics are an elegant narrative of grief and carrying on: the way the weather stays stubbornly lovely and coffee still tastes good. You don’t need words to feel the emotion here – even the instrumental puts a lump in your throat.

"Disintegration" by The Cure

Image: Fiction Records

16. “Disintegration” by The Cure

Robert Smith isn’t known for being a cheery bloke: even his most upbeat pop songs get pretty dark as soon as you start listening to the lyrics. But he was on particularly gloomy form in 1989, putting together the biggest, best and bleakest album of The Cure’s career: Disintegration. Though it was the singles “Pictures of You” and “Lullaby” that got the airtime, the monster lurking in its depths was the title track: an eight-minute serpent of a song that twisted this way and that and turned pitiless eyes on the dissolution of a relationship. 

"Famous Blue Raincoat" by Leonard Cohen

Image: Columbia

17. “Famous Blue Raincoat” by Leonard Cohen

Old Len has a legendary knack for gloom, but he’s never sounded as bitter as he did addressing the man who stole his (fictional) wife on “Famous Blue Raincoat” in 1971. As a poem or monologue it’s a masterpiece: listening to it is like accidentally spying on somebody else’s broken marriage, where all the pain is masked by repression and resignation. The singer only really lashes out once or twice – “my brother, my killer” — ouch — and saves the bite in his voice for the sign-off: “Sincerely, L Cohen.” That’s how you kill with kindness.

"Re: Stacks" by Bon Iver

Image: Jagjaguwar

18. “Re: Stacks” by Bon Iver

Never has something so incoherent inspired so many feels. It’s hard to tell what Justin Vernon is singing about at the best of times, but when a song begins “This my excavation/And today is Kumran” and climaxes with something about backs, racks and stacks, you know someone’s going pretty hard for the whole “cloaked in metaphor” thing. Nevertheless “Re: Stacks” is the emotional centrepiece of Bon Iver’s lo-fi masterpiece For Emma, Forever Ago, balancing heartbreak and healing with stark and simple beauty. Even if it does include the phrase “crispy revelation.”

"Boots of Spanish Leather" by Bob Dylan

Image: Columbia Records

19. “Boots of Spanish Leather” by Bob Dylan

This spine-tinglingly sad ballad is just Dylan’s restless voice stretching out over a solo guitar refrain. The song tells of a woman asking her lover what she should bring back for him from her travels. All he wants, he replies, is her back safe and sound. But when she writes to say she’s not sure when she’ll return, her man realises she’s left him behind and puts in a request. Those Spanish boots are the death knell to their relationship and a potent symbol of a horribly broken heart. Sigh.

"Brick" by Ben Folds Five

Image: Epic

20. “Brick” by Ben Folds Five

A somber departure from the pianist’s otherwise playful catalog, “Brick” was written as a way for Folds to cope with the guilt of his high-school girlfriend’s abortion on the day after Christmas. Taking on multiple perspectives and a massive shot of empathy, the song traces the day from start to devastating finish, circling back to that cutting chorus “She’s a brick and I’m drowning slowly” with increasingly desprate results. 

"Isolation" by Joy Division

Image: Factory

21. “Isolation” by Joy Division

Where do you even start with Joy Division? Nearly every song recorded by the band before Ian Curtis’s suicide in 1980 deserves a place on a playlist like this. Ducking the obvious (“Love Will Tear Us Apart”) and the totally harrowing (“New Dawn Fades”), we’ve picked “Isolation” for its chilly synths, peppy bassline and urgent sense of desperation: “Mother, please try to believe me/I’m doing the best that I can/I’m ashamed of the things I’ve been put through/I’m ashamed of the person I am.” Doom and despair with a disco beat.

"Shipbuilding" by Robert Wyatt

Image: Rough Trade

22. “Shipbuilding” by Robert Wyatt

Elvis Costello wrote the lyrics for this poignant reaction to the Falklands War of 1982, but though Ol’ Dec’s own version is fantastic in itself, it’s Wyatt’s strained vocal that lifts this from heartfelt to gut-wrenchingly beautiful. And that bass that sounds like lurching timber hulls and the loss of so many in an avoidable conflict? That’s ska bassist Mark Bedford swapping Madness for sadness.

"A Change Is Gonna Come" by Otis Redding

Image: Volt

23. “A Change Is Gonna Come” by Otis Redding

Sam Cooke’s 1963 original is magnificent, a triumph of nobility in the face of lifelong suffering. But the Otis Redding version just sounds crushed, the song’s civil rights-era message of hope overwhelmed by widescreen orchestral despair. Following a weary, last-post trumpet salvo, Otis enters the song moaning like a dying man, clutching at the straws of promised change while clearly not believing a word of it. Fatalism never sounded so lush and lovely.

"Enjoy the Silence" by Depeche Mode

Image: Mute

24. “Enjoy the Silence” by Depeche Mode

Basildon’s own synthpop superstars tend to operate somewhere between sleaze and sadness, and this cut from their awesome Violator album is definitely towards the latter end of that scale. There’s a tragic contradiction at the heart of “Enjoy the Silence”: words are violent and damaging, sure, but often they’re the only way we can express the pain that they themselves cause. After all, this song wouldn’t be nearly as devastating as an instrumental.

"Blue" by Joni Mitchell

Image: Reprise

25. “Blue” by Joni Mitchell

“Songs are like tattoos,” sings Joni here, and this one is a complicated piece: crowns and anchors, waves and shells, “acid, booze and ass, needles, guns and grass,” all worked together into something rich, strange and mournful. Is it about the end of an affair? An era? A dream? Joni’s not telling, but the song will last even longer than that wonky dragon you got in Thailand.