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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.

  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.

2. Glasvegas – ‘Daddy’s Gone’

Glasvegas’ debut single was a heartfelt, tear duct-crinkling track about a kid’s dad leaving. “Forget your dad/ He’s gone,” sang James Allen, as the music tugged at the heart strings via doo-wop and some Spector-ish production.

3. Robyn – ‘Dancing On My Own’

Instead of putting something by ABBA in the list, we’ve gone for this slice of sad Scandipop from Robyn. The idea of Ms. Carlsson attempting her biggest, boldest moves while the guy she’s trying to impress just ignores her is pretty depressing.

4. Bone Thugs-N-Harmony – ‘Tha Crossroads’

Whenever a musician passes away, one can’t help but think of ‘Tha Crossroads. Bone Thugs-N-Harmony’s track dedicated to NWA’s recently departed Eazy-E (who was also the group’s mentor) has to go down as one of the most unhappy hip-hop songs ever. 

5. Peter Gabriel – ‘Mercy Street’

It’s perhaps a little known fact that one of Peter Gabriel’s biggest lyrical inspirations was confessional poet Anne Sexton.

6. Frank Ocean – ‘Swim Good’

This track has prompted many spods to attempt to decipher what happens at the end of the song.

7. Bruce Springsteen – ‘The River’

Springsteen is so skilful in his narrative about dreams dying, that you think you are the one living in the waking nightmare he paints. Obvs, ‘The River’ is the best musical metaphor ever as well.

8. Lou Reed – ‘The Kids’

“Mummy! Mummy!” Oh gosh, those infant screams will have you feeling incredibly low for the best part of an hour after you’ve heard them.

9. The Smiths – ‘This Night Has Opened My Eyes’

Richard Ashcroft might have sung sullenly about “cats in a bag, waiting to drown,” but Morrissey got their first with this tale about cheery baby/water/infanticide.

10. Joy Division – ‘Love Will Tear Us Apart’

Like a slow walk towards death, the lyrics of ‘Love Will Tear Us Apart’ read like a pretty explicit suicide note. If this was a Crimewatch reconstruction, this would be the massive ‘well, DUH’ moment.

11. Johnny Cash – ‘Hurt’

Coming to Trent Reznor’s ‘Hurt’, Johnny Cash’s weight of experience gave the song a sepia-tinged world-weariness which was deeply affecting on many levels.

12. 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.

13. 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.

14. “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.

15. “No Distance Left to Run” by Blur

Damon Albarn was locked into 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.

16. “The Boxer” by Simon & Garfunkel

In which Paul Simon condenses the Great American Novel into a folk song

17. “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.

18. “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

19. Lazarus” by David Bowie

Bowie’s final album often plays like a self-written obituary, and its breakout single’ haunting horn jabs and slow tempo suggest a death march.

20. “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.

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