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Far Out 40: The greatest breakup songs of all time

“I can’t be worried about that shit. Life goes on, man.” – His Dudeness, Jeff Lebowski, 1998. 

In his novel High Fidelity, Nick Hornby muses: “What came first – the music or the misery?” This is one of many philosophical cogitations that his jaded broken-hearted protagonist wearily tries to resolve. The answer, of course, is that the only purpose of music is to offer a salve to said misery. But in the self-perpetuating miasmatical stink of a breakup, the dirty thoughts that your mind farts out can leave you listening to a dangerously devastating deluge of songs.

Slowly, just as Hornby did, these tracks bring forth their own questions, such as: “People worry about kids playing with guns, and teenagers watching violent videos; we are scared that some sort of culture of violence will take them over. Nobody worries about kids listening to thousands – literally thousands – of songs about broken hearts and rejection and pain and misery and loss.” But, alas, at least you’re thinking about music, albeit it in a morose mood, and not the ahem

Thus, with musical distraction in mind, we have crafted the ultimate playlist that takes you through the varying stages of a breakup and like Andy Dufresne you can crawl through this river of shit and come out clean on the other side.

Naturally, we have avoided the cliched realm of Whitesnake, but other than that these are all tracks to be enjoyed even when the dust has long since settled. Please enjoy responsibly…

The ultimate breakup playlist:

Stage One: The mournful “poor me” songs…

At the height of devastation, there is a dramatic melodrama in the air. Only the most crushingly sad songs can fit your despairing mood. We’ve tried to capture the hysteria without delving towards the demented.

  • ‘Today I Sing the Blues’ by Aretha Franklin
  • ‘All I Could Do Was Cry’ by Etta James
  • ‘Lover, You Should’ve Come Over’ by Jeff Buckley
  • ‘I Can’t Make You Love Me’ by Bonnie Raitt
  • ‘Someone Like You’ by Adele
  • ‘Hurt’ by Johnny Cash
  • ‘Lover’s Spit (Redux)’ by Broken Social Scene
  • ‘About Today’ by The National
  • ‘Love is All’ by The Tallest Man on Earth
  • ‘These Days’ by Nico

Stage Two: Dower but defiant…

The dust has now settled. The photo frames are no longer turned face down like a meticulous poltergeist has been around. This is the moment in time when the likes of Bob Dylan, Joni Mitchell and Leonard Cohen, who have seemingly endured a thousand break-ups between them (sometimes with each other), come into their own.

This trio of experts will be sages on your journey beyond this playlist, they are battle hardy and when it comes to Blonde and Blonde and Blood on the Tracks, Dylan proves that old adage about a bad thing that doesn’t kill you…

  • ‘Don’t Think Twice, It’s All right’ by Bob Dylan
  • ‘Hey, That’s No Way to Say Goodbye’ by Leonard Cohen
  • ‘Working Titles’ by Damien Jurado
  • ‘Both Sides Now’ by Joni Mitchell
  • ‘Nobody’s Baby Now’ by Nick Cave & The Bad Seeds
  • ‘Clay Pigeons’ by Blaze Foley
  • ‘Tiny Tears’ by Tindersticks
  • ‘How Can You Mend a Broken Heart’ by Al Green
  • ‘Heavy Heart’ by You Am I
  • ‘It’s hard to get around the wind’ by Alex Turner
  • ‘Living Without You’ by Randy Newman

Stage Three: The bitter revolt…

It most certainly wasn’t your fault.

You will now rage, a mellow sort of thunder, against the only mistake you ever made: being mystically coerced by some sort of bastardly Svengali who has really let themselves go lately. 

  • ‘You Goin’ Miss Your Candyman’ by Terry Callier
  • ‘I Am a Rock’ by Simon & Garfunkel
  • ‘Positively 4th Street’ by Johnny Rivers
  • ‘I Couldn’t Say It To Your Face’ by Arthur Russell
  • ‘Mariners Apartment Complex’ by Lana Del Rey
  • ‘No Woman, No Cry – Live at the Lyceum’ by Bob Marley
  • ‘You’re Breakin’ My Heart’ by Harry Nilsson
  • ‘The Night Josh Tillman Came to Our Apt.’ by Father John Misty
  • ‘(I Married a) Monster from Outer Space’ by John Cooper Clarke
  • ‘Go Your Own Way’ by Fleetwood Mac
  • ‘Better Days’ by Graham Nash

Stage Four: The faux “over it” loose cannon…

At this stage, you will become that friend who texts you for a “quiet drink” on a Tuesday and when you arrive, they’ve got a Tequila slammer awaiting you and mercilessly ensnare you in their wicked all-night plan. 

  • ‘The Lost Art of Keeping A Secret’ by Queens of the Stone Age
  • ‘20th Century Boy’ by T. Rex
  • ‘It’s My Life’ by Talk Talk
  • ‘Been down so Long’ by The Doors
  • ‘Good Times Bad Times’ by Led Zeppelin

Stage Five: The exultant other side…

The proverbial sun has broken through the figurative clouds and boy does it feel warm… Whether it be a breakup or a lost job, failed test or anything else that has got you looking up sad songs on the internet, these exultant tracks are pieces of art that remind us all of a lesson constantly in the learning – that so often in life you eventually find yourself gladdened that it didn’t work out the way you wanted it to. 

  • ‘Cycles’ by Frank Sinatra
  • ‘One Fine Morning’ by Bill Callahan
  • ‘True Love Will Find You In the End’ by Daniel Johnston 

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