50 beautifully sad songs

Anthems to soothe your soul

A recent study found pop music has got “sadder” in the past 30 years. But that’s not a bad thing, as our playlist of beautifully sad songs proves…

Amy Winehouse – ‘Back To Black’.

Recently we made a playlist of the 50 most uplifting songs ever. Now, we look at the opposite: 50 beautifully sad songs, beginning with Amy Winehouse – ‘Back To Black’. Beneath the brassy exterior, Winehouse had a real fragility that was never better bared than on this iconic track, and its monochrome video.

Arctic Monkeys – ‘Love Is A Laserquest’.

Arctic Monkeys – ‘Love Is A Laserquest’. On the face of it, a laserquest should be a great day out. Of course, there’s more to this sad tale than that. Alex Turner’s on typically brilliant form here lyrically. It’s a bleak, desperate picture of heart-break.” I’ll pretend that you were just some lover,” he says – but we all know he’s kidding himself.

Frank Ocean – ‘Swim Good’.

Frank Ocean – ‘Swim Good’. The lyrics to Frank Ocean’s breakthrough song paint a dark picture of a heartbroken, suicidal man planning to drive his Lincoln car into the ocean. Soulful desperation at its best.


The Beatles – ‘Eleanor Rigby’.

The Beatles – ‘Eleanor Rigby’. Paul McCartney’s baroque masterpiece told a darkly lonely story about a woman who “died in the church and was buried along with her name – nobody came.” McCartney originally named the song’s protagonist a more cheery Miss Daisy Hawkins.

Radiohead – ‘Street Spirit’.

Radiohead – 'Street Spirit'.

Radiohead – ‘Street Spirit’. Even Thom Yorke thinks this is one of Radiohead’s saddest songs, describing it as “”the dark tunnel without the light at the end”. Didn’t sound quite so sad when recently covered by The Darkness, though.

Blur – ‘This Is A Low’.

Blur – 'This Is A Low'.

Blur – ‘This Is A Low’. Britpop wasn’t all about knees-ups and ‘cor blimey, missus’ type stuff. This plaintive song from ‘Parklife’ is Blur’s most beautifully hopeful track. The shipping forecast has never sounded so loaded.

The Cure – ‘Pictures Of You’.

The Cure – 'Pictures Of You'.

The Cure – ‘Pictures Of You’. The goth image means The Cure are unfairly painted as masters of the morose, and it’s not always true. ‘Pictures Of You’ is, however, fairly desolate stuff, allegedly inspired by a house fire that left just the photos in his wallet.


Pink Floyd – ‘Wish You Were Here’.

Pink Floyd – 'Wish You Were Here'.

Pink Floyd – ‘Wish You Were Here’. Alienation was a common theme in Roger Waters’ lyrics, but he never nailed it so succinctly or poignantly as in this song, the title track from the 1975 album. “We’re just two lost souls swimming in a fish bowl, year after year,” it says.

Flaming Lips – ‘Do You Realize?’,

Flaming Lips – ‘Do You Realize?’, “That everyone you know will someday die?” asks Wayne Coyne. It’s not the sort of fact of life you want to tackle at a festival but hearing this with all your friends under the stars rocks. It’s sad but also uplifting, particularly the shamelessly manipulative key changes.

Nick Drake – ‘Pink Moon’.

Nick Drake – 'Pink Moon'.

Nick Drake – ‘Pink Moon’. A tragic character himself, Nick Drake’s glorious music tapped into a beautiful, calm and very English form of melancholy.

Alex Turner – Piledriver Waltz’.

Alex Turner – Piledriver Waltz’. From the brilliant ‘Submarine’ soundtrack, this song starts off with some of the greatest lyrics, as quoted by you, the readers: “I etched a face of a stopwatch/ On the back of a raindrop.” It’s a miserable theme – he’s heard that the lady is going to dump him – with a stunning rhythmic change that prevents it from being a Debbie Downer.


The Velvet Underground – ‘Candy Says’.

The Velvet Underground – ‘Candy Says’. Written about transexual Candy Darling, the New York socialite and member of Andy Warhol’s coterie, The Velvet Underground find sadness and shyness beneath the exterior in this small, delicate, slow song. “Candy says, ‘I’ve come to hate my body’,” it begins.

The National – ‘Sorrow’.

The National – ‘Sorrow’. Depression is not an easy thing to talk about, nor sing about, but this bleak track by The National feels suitably spiralling and claustrophobic. “Sorrow found me when I was young, sorrow waited, sorrow won,” it says.

Elliot Smith – ‘Needle In The Hay’.

Elliot Smith – 'Needle In The Hay'.

Elliot Smith – ‘Needle In The Hay’. It’s hard to separate thoughts of Elliott Smith’s music from thoughts of his tragic demise. He always seemed like a troubled soul, and especially on this desperate track, used to great effect in Wes Anderson’s The Royal Tenenbaums.

Grizzly Bear – ‘Slow Life’.

Grizzly Bear – ‘Slow Life’. It’s always a pleasant surprise how good the Twilight soundtracks are. The ‘New Moon’ included this track by the Brooklyn four-piece featuring Victoria Legrand on vocals. The song plays during a scene where Bella drowns. So that’s cheery then!

Kasabian – ‘Goodbye Kiss’.

Kasabian – ‘Goodbye Kiss’. “Open you’re eyes and what do you see? The last stand, let go of my hand” could be the most poignant thing Kasabian have ever written. They’re in nostalgic mood, looking back to the rock ‘n’ roll days that sent them insane. You’ve still got a bit of life in you yet, lads!

Pearl Jam – ‘Black’.

Pearl Jam – ‘Black’. The band refused to release ‘Black’ as a single despite heavy pressure from their label. Eddie Vedder stated that “fragile songs get crushed by the business. I don’t want to be a part of it. I don’t think the band wants to be part of it.” You’ve got to give him respect for that.

LCD Soundsystem – ‘All I Want’.

LCD Soundsystem – ‘All I Want’. All James Murphy wants his ‘your pity’ and ‘your bitter tears’. All we want if for him to start up LCD Soundsystem and headline a major festival next year. The fourth track from 2010 album ‘This Is Happening’ contains one of the greatest, weirdest bass lines in music history.

The Verve – ‘The Drugs Don’t Work’.

The Verve – ‘The Drugs Don’t Work’. Was it about recreational drugs or medication? It’s something that’s never really been cleared up. One thing’s for certain: this song taps into a kind of sweet-sad ennui that was the polar opposite of The Verve’s trademark swagger.

Sharon Van Etten – ‘We Are Fine’.

Sharon Van Etten – ‘We Are Fine’. “Trying hard to breathe, head between my knees/ take my hand and squeeze, say I’m alright,” says Van Etten in one of the most wrenching songs on her desolate album ‘Tramp’. “We’re alright” and “I’m alright” are repeated so often in this song they become a kind of mantra to get through. “It’s OK to feel” soothes Beirut’s Zach Condon.

Johnny Cash – ‘Hurt’.

Johnny Cash – ‘Hurt’. Though it’s a cover of a Nine Inch Nails song, the late Johnny Cash brought a fragile poignancy to this track. It was the sound of a man who had lost his true love, and was himself staring death in the face. A beautiful, painful listen.

Neil Young, ‘The Needle And The Damage Done’

Neil Young, 'The Needle And The Damage Done'

Neil Young, ‘The Needle And The Damage Done’ Heroin was rife among the California scene that Neil Young mixed in, and this song, written about Crazy Horse guitarist Danny Whitten, is a stark, heartbreaking observation on drug use.

Perfume Genius – ‘Rusty Chains’.

Perfume Genius – ‘Rusty Chains’. Perfume Genius’s music is so heartbreakingly sad that even he cries at his live shows, as well as the rest of the audience. Mike Hadreas (he’s not really called Perfume Genius, silly) explained its meaning: “It’s a song for a man whose lover has died. He asks to be taken next, so they can be together again.”

Portishead – ‘Glory Box’.

Portishead – 'Glory Box'.

Portishead – ‘Glory Box’. The Bristol trip-hop group track from their unbelievable debut ‘Dummy’ is an uneasy, ambiguous love song. “I just want to be a woman,” cries Beth Gibbons. It’s a drowsy hymn of defeat that’s been covered by many and used on numerous film soundtracks, includingThe Craft and Stealing Beauty.

Joni Mitchell – ‘A Case Of You’.

Joni Mitchell – ‘A Case Of You’. Anyone who has lost love, listened to this song and not bawled their eyes out is a bonafide psychopath. The central conceit – “Oh I could drink a case of you darling/ Still I’d be on my feet” – is overshadowed by the first line – “just before our love got lost you said I am as constant as a northern star”. Anyone got a tissue?

Nick Cave – ‘People Ain’t No Good’.

Nick Cave – ‘People Ain’t No Good’. The saddest misanthropic anthem of all time. Love is gone and Cave is down on the world: “It ain’t that in their hearts they’re bad, they’d stick by you if they could/ But that’s just bullshit baby, people just ain’t no good”. Gulp.

Bonnie Prince Billy – ‘Death To Everyone’.

Bonnie Prince Billy – ‘Death To Everyone’. A song so desolate – ‘death to you, death to me’ – I’m not sure what environment it calls for. It’s a rant and shrug at the universe from the album ‘I See A Darkness’ which has the fitting cover art of an evil-looking skull.

Bon Iver – ‘Skinny Love’.

Bon Iver – ‘Skinny Love’. ‘For Emma, Forever Ago’ was the breakthrough album from Justin Vernon’s Bon Iver which he wrote and recorded while recuperating from some shit in a cabin in Wisconsin. ‘Skinny Love’ is about not wanting to end a relationship but knowing you have to (probably).

Walker Brothers – ‘Sun Ain’t Gonna Shine Anymore’.

Walker Brothers – 'Sun Ain't Gonna Shine Anymore'.

Walker Brothers – ‘Sun Ain’t Gonna Shine Anymore’. Loneliness, emptiness, tears, no sun and a blue coat. It’s not looking up for the Walker Brothers is it? Also “The sun ain’t gonna shine any more… when you’re without her” is probably the worst thing to say if you’re comforting a heartbroken pal.

Bat For Lashes – ‘Laura’.

Bat For Lashes – ‘Laura’. The first track to be heard from Natasha Khan’s ‘The Haunted Man’ is a beauty. ‘Laura’ sounds like a bit of a party girl with a penchant for wearing glitter and dancing on tables. But inside she’s hollow. “Oh, Laura, you’re more than a superstar,” sings Khan, but her friend just wants to go out on the piss.

Morrissey – ‘Every Day Is Like Sunday’.

Morrissey – ‘Every Day Is Like Sunday’. Perhaps the definitive song about getting the Sunday blues, Moz directs his ire at the grease-tea and deals of a silent and grey coastal town “that they forgot to bomb”. Not the best person to go on holiday with, then.

Antlers – ‘Kettering’.

Antlers – ‘Kettering’. The second song on ‘Hospice’, the concept album about the relationship between a hospice worker and a patient dying of bone cancer, doesn’t take any prisoners. We’ll never know if the album is autobiographical but this song sounds so genuinely poignant there must be some truth in the story.

Sufjan Stevens, ‘John Wayne Gacy Jr’.

Sufjan Stevens, ‘John Wayne Gacy Jr’. This track from ‘Illinois’ tells the story of 1970s serial killer John Wayne Gacy Jr. Stevens sings about the childhood abuse Gacy suffers and references his use of ‘chloroform’ with his victims and his nickname ‘Killer Clown’. It’s a sorrowful number made all the more potent because it’s true.

Yeah Yeah Yeahs – ‘Maps’.

Yeah Yeah Yeahs – ‘Maps’. Written about the relationship between Karen O and Liars frontman Angus Andrew, ‘Maps’ describes them being pulled apart on respective tours. Karen O’s tears in the video are real – ironically, because Angus was hours late to the video shoot and Yeah Yeah Yeahs were about to set off on tour.

Grandaddy – ‘Everything Beautiful Is Far Away’.

Grandaddy – 'Everything Beautiful Is Far Away'.

Grandaddy – ‘Everything Beautiful Is Far Away’. If David Bowie’s ‘Space Oddity’ was a song about the terror of floating uncontrollably into space, this song was about what happens when you land, the reminiscences of a space traveller lost in a desolate world.

Dolly Parton – ‘Jolene’.

Dolly Parton – 'Jolene'.

Dolly Parton – ‘Jolene’. There’s pure desperation in this stunning Dolly Parton song, once covered by The White Stripes. In it, Parton takes the role of a desperate woman appealing to the beautiful Jolene not to steal her husband. “You could have your choice of men, but I could never love again,” it says, crushingly.

Ben Folds Five – ‘Brick’.

Ben Folds Five – 'Brick'.

Ben Folds Five – ‘Brick’. Though it’s not immediately obvious, this track describes the process of taking a girlfriend to get an abortion. It’s the sensitivity with which Ben Folds describes the experience – the cold car seat, the feeling of uselessness – that makes this track so uniquely moving.

Ryan Adams – ‘The Shadowlands’.

Ryan Adams – ‘The Shadowlands’. No one does simple vocals and piano like Ryan Adams, particularly on 2004 album ‘Love Is Hell’. He’s also master of the image. In ‘The Shadowlands’, roaches climb the walls, mummy hides the pearls, she’s angry like a salesman. Deft sketches that say so much.

The Smiths – ‘I Know It’s Over’

The Smiths – 'I Know It's Over'

The Smiths – ‘I Know It’s Over’. Morrissey has unleashed more than his fair share of forlorn lyrics on the world, but he’s never been more desolate than on this track. “Oh mother, I can feel the soil falling over my head,” it begins.

Death Cab For Cutie – ‘Transatlanticism’.

Death Cab For Cutie – 'Transatlanticism'.

Death Cab For Cutie – ‘Transatlanticism’. Released in 2003, this is the kind of indie power balladry that would have soundtracked a tearful goodbye on The OC, a song about being separated from the ones you love in which the power lies in its minimalism.

Blur – ‘No Distance Left To Run’.

Blur – 'No Distance Left To Run'.

Blur – ‘No Distance Left To Run’. Describing a painful break-up between Damon Albarn and Elastica’s Justine Frischmann, ‘No Distance Left To Run’ is a painful song for the singer to perform. “It upsets me, that song,” Albarn has said. “To sing that lyric I really had to accept that that was the end of something in my life.”

Sparklehorse, ‘Sad And Beautiful World’.

Sparklehorse, 'Sad And Beautiful World'.

Sparklehorse, ‘Sad And Beautiful World’. This song is sad enough to begin with but if you’re a Sparklehorse fan, jeez, you’re going to be sobbing. Singer Mark Linkous died in 2010, having battled depression for most of his life. If you can bear the sorrow, this is a perfect song to remember him by.

Bruce Springsteen – ‘The River’.

Bruce Springsteen – ‘The River’. It may have been released 31 years ago, but there’s a topicality to ‘The River’s’ tale of a young couple struggling to survive in tough economic times in a dead-end town. The harmonica is haunting, and pained.

Leonard Cohen – ‘Famous Blue Raincoat’

Leonard Cohen – 'Famous Blue Raincoat'

Leonard Cohen – ‘Famous Blue Raincoat’ “It’s four in the morning, the end of December,” begins this mournful letter-in-song by the high priest of melancholy. If anyone tells you Leonard Cohen is music for depressives, they’ve probably heard this song.

Sinead O Connor – ‘Nothing Compares 2 U’.

Sinead O Connor – ‘Nothing Compares 2 U’. She didn’t write the song (Prince did), but you can tell Sinéad O’ Connor feels every word of this timeless break-up song. The two tears that roll down her cheek in the video were, apparently, not faked.

Bright Eyes – ‘Nothing Gets Crossed Out’.

Bright Eyes – ‘Nothing Gets Crossed Out’. You can hear Conor Oberst’s voice shaking in this look back to the past and fearful glance to the future. It’s a powerful, clear description of the paralysis of fear: “But all I do is just lay in bed And hide under the covers”. Does anyone else think Bright Eyes would be a lot better if they changed their name?

Radiohead – ‘How To Disappear Completely’.

Radiohead – ‘How To Disappear Completely’. “I’m not here’, “this isn’t happening”… sounds like someone wants a break. Bingo! Thom Yorke’s lyrics come partly from the advice he received from Michael Stipe about the pressures of touring. Listen out for Johnny Greenwood on the ondes martenot.

Robert Wyatt – ‘Shipbuilding’.

Robert Wyatt – 'Shipbuilding'.

Robert Wyatt – ‘Shipbuilding’. Plunging basslines and fragile vocals spin an intricate capsule story, the idea of a struggling industrial community getting by making of ships that their sons are then sent off to war in. “With all the will in the world/Diving for dear life/When we could be diving for pearls.” Gets you in the gut.

Jeff Buckley – ‘Morning Theft’.

Jeff Buckley – ‘Morning Theft’. Made all the more poignant by Jeff Buckley’s untimely death at the age of 30 in Memphis, Tennessee, ‘Morning Theft’ is an under-appreciated gem from his second, unfinished album, ‘…My Sweetheart The Drunk’. “I miss my beautiful friend”, he sings, before the song changes gear sweetly and unexpectedly. We miss you, Jeff.

Anthony & The Johnsons – ‘Hope There’s Someone’.

Anthony & The Johnsons – ‘Hope There’s Someone’. You only have to hear the first line of Anthony’s most famous song to want to go to bed and cry and eat yoghurt for weeks. It was released in 2005 and remains one of the greatest songs of the 21st century. 50 beautifully sad songs – Spotify playlist