The 50 best sad songs ever written

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. Andrzej Lukowski

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.

On their first album, the Brooklyn dance-punk troupe partied with their tongue set firmly in cheek, delivering odes to Daft Punk and hipster braggadocio. With its followup, 2007’s Sound of Silver, the band both improved its grooves and grew up as songwriters. Frontman James Murphy was inspired to write this unexpectedly moving rumination on grief following the death of his therapist and the specific void left in his wake: ‘I wish that we could talk about it/But there, that’s the problem.’ The twinkling bells and electronic bloops evoke images of a clear night sky, underscoring Murphy’s main point - no matter who we lose, somehow, the world keeps turning. 

Mondays aside, 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. 

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.

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.’

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.

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. This isn’t sudden sorry: It’s lived-in melancholy dripping with pragmatism.

A year after indie rockers The Verve Pipe scored an unlikely hit with a morose song about an unwanted pregnancy and its psychological toll, Ben Folds scored a mainstream breakthrough with this 1997 radio hit. 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. 

In 1969, suffering from a collapsed lung and TB, Cat Stevens was told he had only had a few weeks to live. He wrote some of his greatest songs, including ‘Trouble,’ while stuck in a spartan hospital in Sussex. Riddled with pain and a sense of injustice, it ends abruptly and bleakly: ‘I don’t want no fight/And I haven’t got a lot of time.’ Stevens actually survived, lived through a near-drowning a few years later and eventually found peace in religion. But that doesn’t make ‘Trouble’ any less troubling.

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.

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.

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.

The Shangri-Las were responsible for a whole string of teen-pop tragedies in the ’60s: doomed love, heartbreak and motorbike crashes were all grist for their mill. ‘Past, Present and Future’ is the saddest of the lot, a quietly chilling story set to Beethoven’s ‘Moonlight Sonata.’ What happened out there on the beach that night, somewhere between the second and third verses? The softly spoken narrator sounds like she’ll take that secret to her grave.

Sufjan’s Carrie & Lowell is an often unbearably sad meditation on the passing of the mother who walked out on him when he was a baby. But the first track cuts the deepest: it’s a final farewell to his mother in which he refuses to pity himself but instead takes pity on her, sighing, ‘You’ll never see us again.’

Glen Campbell first took Jimmy Webb’s break-up song ‘By the Time I Get to Phoenix’ for a spin in 1967, and brought it home in under three minutes. Two years later it was carjacked by the velvet-voiced Isaac Hayes and driven all the way to Soulsville. After nine minutes of sad backstory, Ike finally reaches Webb’s three verses – then keeps on motoring, way past Oklahoma and onto unmarked roads as the strings and horns swell. This is technicolour heartbreak on scale so epic it makes Glen Campbell sound like a kid in a pedal car.

The Philly vocal group dominated the charts in the ‘90s largely with old-fashioned R&B songs about love and loss, and few of their hits spur the waterworks quite like this acapella flip of a relative Motown obscurity. Is it about losing a loved one? The end of a relationship? High school graduation? Honestly, all can apply, depending on whatever the listener happens to be going through at the time - which is a large part of its enduring genius. 

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.

MJB's Grammy-winning ballad hits home because, like all of her best work, it's completely real. Yes, she and her man have been written off by others. Yes, they've been through some sh... stuff. But she knows she just can't be without him, and she wants us to know it. A modern-day classic.

Though Mr O’s been through a break-up, he’s putting on a brave face. Then he spots his ex in the street, feels that lump in his throat and next thing he’s sobbing like a baby. ‘Crying’ reads as a song of defeat, but as that butter-rich voice mounts majestically from octave to octave, The Big O’s tears become a triumph. Let it all out, Roy!

Until the last verse, this never feels like Ian Dury is doing anything other than listing memories of his once-absent father in a wistful stream of consciousness. The natural flow and everyday observations highlight that there are some things we’ll only cherish when it’s too late. 

Featured on Grant’s debut album The Queen of Denmark, this soulful piano ballad may sound like something The Carpenters might have recorded back in the ‘70s. But pay attention to the lyrics and you’ll find they’re all about what happens when you fall head-over-heels way too fast and still feel just a tad bitter about it going wrong: ‘Baby, you’re where dreams go to die/I regret the day your lovely carcass caught my eye.’ Stop drunk-texting your ex and put this on instead.

In 1974 Nick Drake recorded five songs for his fourth album, the sequel to his stark masterpiece Pink Moon. ‘Black Eyed Dog’ was one, documenting the weary singer’s struggles with depression. That album was never finished: in November that year Drake died, aged 26, from an overdose of amitriptyline. ‘Black Eyed Dog’ surfaced years later as a terrible, beautiful testament to a life cut short.

Sung by a young Nick Cave in 1979 and written by Rowland S Howard (guitarist for Cave’s first band The Boys Next Door, later The Birthday Party) at the age of 16, ‘Shivers’ was meant as a tongue-in-cheek dig at overblown teen angst. But Cave’s gloomy delivery and Howard’s spiralling guitar part stripped away the cynicism. The song accidentally turned into an accomplished bit of genuine heartbreak and a cult hit to boot: a happy accident for something so self-consciously miserable.

On this standout track from his Our Love album, Caribou’s Dan Snaith is stuck in the kind of love that hurts – cycling through love, disappointment, resentment and love again: ‘Why’d you have to change your mind/Just as I was changing mine?’ The bittersweet synth melodies are enough to make your heart burst, and to top it all off there’s that sampled fragment of a word, looping round and round throughout the track as if replaying itself over and over in somebody’s memory.

The king of ‘70s singer-songwriter sad, Townes Van Zandt is responsible for some of country’s most bruising ballads, from the outlaw tragedy of ‘Pancho and Lefty’ to the folksy melodrama of ‘Tecumseh Valley.’ This is one of his earliest compositions, an old-fashioned but overpowering tale of hardship, cruelty and drug addiction. Witness the scene from tour doc Heartworn Highways in which Townes uses it to serenade his neighbour, who promptly bursts into tears.

Like a twangy retelling of the gut-wrenching Little Match Girl, Dolly soulfully narrates the wintertime tale of a little girl who shows up on her doorstep, a little dog in tow, looking for warmth and sustenance after being abandoned by her alcoholic parents. In a creepy bit of role-playing, Parton even raises her voice a few octaves to impersonate the voice of the ill-fated child, whose ultimate demise at the crescendo is a gut punch for the ages. Spoiler alert: the dog doesn't make it either. 

With lyrics in place, this gorgeous song from French singer Tellier embodies all the hope and anticipation of a new love affair. But the instrumental makes it an absolute tearjerker, with a lilting piano motif that says wet Parisian streets, broken hearts and the knowledge she’s not coming back. Deliciously French.

Semi-forgotten at home in the UK but still apparently a superstar on the continent, Berry made his name in 1964 with this sentimental pop single. It’s as weepy as they come, especially the bit where he asks the moon for advice on how to get over a break-up, and its unexpected chord changes have been navigated over the years by Boy George, Kylie and many others. This was also the first ever UK hit to feature a wah-wah pedal – not a sound you might immediately associate with tragedy, but that makes it all the more surprising when it hits you right in the heartstrings.

‘When the room is quiet, the daylight almost gone…’ The scene’s set for four-and-a-half minutes of ambient synths and introverted crooning by a bunch of glam kids from Catford. ‘Ghosts’ is a deft sketch of a troubled mind running in ever-narrowing circles. It’s sad, strange and spooky – but somehow it made the singles chart Top Five. The ‘80s were a very weird time.

‘This Woman's Work’ is Kate Bush's most iconic piano ballad, but ‘Moments of Pleasure’ is probably even more poignant. Here, Bexleyheath's finest looks back longingly at friends, collaborators and family members she has lost along the way. Her vocals are exquisite, the orchestral arrangements by movie composer Michael Kamen are stirring without being schmaltzy, and the song itself builds beautifully to a devastating final two verses. When Bush starts singing about her late mother (who succumbed to cancer in 1992, the year before ‘Moments of Pleasure’ was released), you might find you need to take a moment.

December, 1982: I’m at a seventeenth birthday party in a function room in a small Kent town. The girl I am secretly in love with but have never spoken to is dancing to The Jam whilst I lurk just off the dancefloor trying to work up courage. As the DJ drops Culture Club, she turns and kisses the biggest dickhead in the sixth form, and Boy George soundtracks a teenage heart breaking. George wrote ‘Time’ about his secret love for Culture Club drummer Jon Moss, which only makes it sadder: he’s mourning the end of the affair before it even began.

Eccentric indie rockers Of Montreal briefly became the best band in the world when frontman Kevin Barnes poured all his confusion and self-loathing at the collapse of his marriage into this stupendous piece of music (and attendant album Hissing Fauna, Are You the Destroyer?). A brutally honest 12-minute dissection of the relationship from start to end, set to a throbbing, glammed-up motorik backing, ‘The Past is a Grotesque Animal’ is frazzled and harrowing but also thrillingly audacious.

There’s not really much to this one, other than a reminder that misery is eternal and inevitable and though you might be happy now, you’ll end up crying later. Coupled with a mournful earworm of a vocal hook (later sampled by Wu-Tang Clan) and some muted Booker T organ work, that was all the late Wendy René needed to record this tragic classic. She retired from music three years later, turning to religion after the sudden death of her friend and Stax labelmate Otis Redding.

Ever been stuck in a temp job spending your working hours constantly picking over everything that you’ve done wrong in your life? I have. My solution was spending a lot of time on Last.fm listening to minimalist composers. When I got to Gorecki’s ‘Symphony of Sorrowful Songs’, it sounded like the world collapsing in on me. Listening back to it now, it’s almost too grandiose and heartbreaking to be relatable. But sometimes that’s really how bad you feel. Eddy Frankel

Owen Ashworth’s solo project was aptly named, specialising in wrenching portraits of millennial misery – like Girls without the jokes – mumbled in too-tired-for-suicide baritone over chintzy 8-bit keyboard beats. But Ashworth’s observational skill keeps his output firmly on the tragic side of twee. ‘…Creedence’ is a perfect example: a love friendship between two women is left to slip away into a permanent friend zone, while the narrator ekes out a loveless living as a lawyer’s typist.