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The 20 Best Sad Songs Ever Written

There’s nothing like a sad, slow song to aid in a post-breakup cry or to be the soundtrack to a bad day. It’s a well-known fact that music is made to bring out emotions in all of us, but what may come as a surprise is that sad music can have the opposite effect from what you would expect.

Wallowing in sad songs can actually elicit positive feelings of “transcendence, peacefulness, and nostalgia,” according to a recent study.

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. “Hurt” by Johnny Cash

On paper the idea of a country music legend covering Nine Inch Nails sounds absolutely ghastly – even Trent Reznor thought so. But “Hurt” was Johnny Cash’s final triumph, recorded less than a year before his death.

3. “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. 

4. “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.

5. “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.”

6. “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.

7.  “The Boxer” by Simon & Garfunkel

In which Paul Simon condenses the Great American Novel into a folk song. The central story’s a familiar one — Dick Whittington finds out the streets of NYC aren’t paved with gold after all.

8. “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, the record which included the last and greatest part of the ‘No Name’ song series that he’d started on Roman Candle in 1994. 

9. “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.

10. “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. “Look up here, I’m in heaven,” he entones on the erie track released less than a month before his untimely death. One more melancholic masterpiece from the Thin White Duke. 

11. “Strange Fruit” by Billie Holiday

Though she’s also remembered for her version of the harrowing “Gloomy Sunday” (AKA “The Hungarian Suicide Song”), the incredible Ms Holiday left an indelible mark on the culture with “Strange Fruit.” 

12. “The River” by Bruce Springsteen

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.

13. 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.

14. “Neither One of Us” by Gladys Knight and the Pips

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.

15. “Someone Great” by LCD Soundsystem

It’s been said that the lost “someone” of this song was the psychiatrist Dr George Kamen – LCD main man James Murphy dedicated the band’s Sound of Silver album to him.

16. “Disintegration” by The Cure

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.

17. “Famous Blue Raincoat” by Leonard Cohen

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.

18. “Re: Stacks” by Bon Iver

Never has something so incoherent inspired so many feelings. 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.

19. “Boots of Spanish Leather” by Bob Dylan

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.

20. “Brick” by Ben Folds Five

A sombre departure from the pianist’s otherwise playful catalogue, “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.

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