When you’re in a rut sometimes the only tonic is to turn to the saddest songs you know and completely lean into your aching melancholia. We asked Tone Deaf readers what they think the saddest song of all time is, here’s what they came up with.

‘Tears in Heaven’ by Eric Clapton

Clapton penned this song mourning the death of his four-year-old son, Conor, who died after accidentally falling from a 54 story apartment. Following a six month absence from songwriting and performing, Clapton began working on music for the film Rush (1991) with Will Jennings, coming to terms with the grief of his son’s death with this eternally haunting song.

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‘Nutshell’ by Alice in Chains

A 90s grunge staple from Alice in Chains’ 1994 extended play Jar of Flies. Frontman Layne Staley was in the grip of a fatal heroin addiction when he penned the track. A brooding song that muses on loneliness, despair, death, addiction and grappling with fame.

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‘Took the Children Away’ by Archie Roach

Archie Rose’s harrowing 1990 debut single, ‘Took the Children Away’, put the trauma of the enforced separation of Indigenous children from their families under a microscope. Archie’s unflinching song, based on his own life and experiences, was released during a time where there was increased public attention on the Stolen Generations. Roach would go on to be the first songwriter honoured with a Human Rights Achievement Award for the song.

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‘Hurt’ by Nine Inch Nails

Abyssal in its darkness was Nine Inch Nails second album, The Downward Spiral. The record’s most enduring song, album ‘Hurt’, a grave exploration of addiction and despair. Lyrics like “You could have it all / My empire of dirt / I will let you down / I will make you hurt” take up permanent real estate in my psyche from the days spent wallowing in ugly teenage feelings.

‘Hurt’ was immortalised in 2002, with Johnny Cash’s sublime and heart-rending cover. After hearing the cover, Nine Inch Nails frontman Trent Reznor declared “that song isn’t mine anymore.”

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‘Motion Picture Soundtrack by Radiohead

I have relied on the Radiohead discography as a delicious blanket of loneliness and yearning to wrap myself up in. God, choosing which song of theirs to feature in a listicle about the saddest sons ever is like choosing a favourite child. Thankfully I’m not the one that’s been tasked to do it. One of our readers suggested Kid A album closer, ‘Motion Picture Soundtrack’, and I’m inclined to agree.

Written on the same day as ‘Creep’, ‘Motion Picture Soundtrack’ is one of the most unrelentingly depressing songs in the Radiohead archive. “I think you’re crazy, maybe / I will see you in the next life.”

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Hollywood’ by Nick Cave & The Bad Seeds

Ghosteen, the first album Nick Cave penned and recorded following the death of his teenage son Arthur. On album closer ‘Hollywood’, Cave looks to the Buddhist parable of Kisa and the Mustard Seed. “Kisa had a baby, but the baby died,” he sings.

“The Buddhist story of Kisa and the Mustard Seed, that would eventually be the final part of ‘Hollywood’, had been of great significance and comfort to me for years,” Cave wrote on his Red Hand Files. “At some point I jotted it down in verse form, completely independent of anything else, and with no intention of it being a song.”

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‘I Didn’t Understand’ by Elliott Smith

Oh god, Elliott Smith. So many special, sad, lyrics. ‘I Didn’t Understand’ a beautiful manifestation on how depression can transform the human soul into something so bleak! so numb!

“You once talked to me about love and you painted pictures of /
A never-neverland and i could’ve gone to that place /
but I didn’t understand”

Jesus Christ kill me! I want to feel!

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‘Roads’ by Portishead

Whilst we’re on the topic of paralysing depression, ‘Roads’ by Portishead. From their debut record, Dummy. Beguilling and plaintive. “I feel, no more can I say / Frozen to myself / I got nobody on my side /And surely that ain’t right”

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‘Nothing Compares 2 U’ by Sinéad O’Connor

Yes, yes, we all know that it was written by Prince. But it’s ostensibly a Sinéad O’Connor song. The definitive yearning track.

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‘Bright Eyes’ by Art Garfunkel

One of the saddest songs for one of the saddest movies, Art Garfunkel and Mike Batt penned the track for the quite frankly traumatizing Watership Down.

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