Hurt – Johnny Cash

Country icon Johnny Cash was always known for singing some pretty downbeat stuff. However, nothing he ever performed was quite so depressing as his 2002 cover version of Nine Inch Nails’ Hurt. The original recording was bleak enough, but Cash’s version is devastating, particularly when you realise he recorded it whilst mourning the loss of his wife, and would himself pass away soon thereafter.

Comfortably Numb – Pink Floyd

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Roger Waters of Pink Floyd was never the cheeriest fellow, but when writing the lyrics for 1979’s Comfortably Numb, he really outdid himself. Inspired by a real-life episode when Waters was tranquilized before a gig, the track powerfully conveys feelings of alienation from the world at large, and Dave Gilmour’s mournful vocals and guitar solos take it to another level.

Take This Waltz – Leonard Cohen

Such was the gloominess of Leonard Cohen, he could have sung If You’re Happy and You Know It Clap Your Hands and make it sound like the saddest thing you’d ever heard. His tribute to Spanish poet and playwright Federico García Lorca (with lyrics based on one of Lorca’s poems) is one of the most painfully poignant things Cohen ever recorded.

Mother – John Lennon

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Soon after leaving The Beatles in 1970, John Lennon underwent a radical form of therapy to deal with unresolved childhood trauma, not least feelings of loss and abandonment in relation to his mother. The song Mother came from this, and the results make for difficult listening thanks to the blunt, harrowing lyrics, and Lennon’s fierce, grief-stricken delivery.

Exit Music (For a Film) – Radiohead

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Radiohead have always been champions of music to drown in your own tears to. Combine that naturally downbeat temperament with Romeo & Juliet – a tale renowned for its less-than upbeat conclusion – and you’ve got a recipe for something spectacularly depressing. Written specifically for the 1996 film of William Shakespeare’s play, the song also wound up on the British band’s classic 1997 album OK Computer.

Love Will Tear Us Apart – Joy Division

Any song that is released as a single in the wake of its singer-songwriter’s suicide is invariably going to carry a distinct strain of despair. 1980’s Love Will Tear Us Apart proved to be Joy Division’s best-known song, but decades of heavy airplay haven’t detracted from its raw emotional power, as the tragic Ian Curtis bids farewell to both his failing marriage, and life itself.

Mad World – Michael Andrews and Gary Jules

When Tears for Fears originally recorded Mad World in 1982, it had a modest impact – but the version recorded for the soundtrack of 2001 film Donnie Darko really struck a chord. Bizarrely, the haunting cover from singer Gary Jules and pianist Michael Andrews (who never released another single) topped the British singles chart at Christmas 2003, proving just how depressed people get in the Holidays.

That Joke Isn’t Funny Anymore – The Smiths

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For generations, British indie pioneers The Smiths have been the premier go-to band of choice for angst-ridden adolescents. The band’s songs about depression and alienation number in the dozens, but arguably none are quite so brutally despairing as their 1985 single That Joke Isn’t Funny Anymore. Propelled by Morrissey’s anguished lyrics and vocals and Johnny Marr’s haunting guitar work, it’s a gut-wrenching rumination on loneliness.

One – Metallica

Any song whose chorus contains the lyrics “Hold my breath as I wish for death, please God wake me” clearly isn’t the happiest little ditty you’re ever likely to hear. At once one of the gentlest yet harshest things Metallica have recorded, 1988’s One envisions the plight of a landmine victim left without limbs, sight, speech or hearing, yet still alive. A grim thought indeed.

The Show Must Go On – Queen

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Queen’s Freddie Mercury was always the voice of hope in the face of adversity. However, this is all but gone on 1991’s The Show Must Go On, the band’s last single released in Mercury’s lifetime, which sees the legendary singer bluntly confront the fact that his days were numbered (although Brian May actually wrote most of the lyrics). Not exactly the most uplifting Queen song.