Bringin’ On the Heartbreak

Once again Worn Fashion Journal’s Annual Valentine’s Heartbreak Karaoke night is fast approaching. You are, of course, welcome to sing any song from our catalogue, but it is Valentine’s Day, and we’re hoping you’ll wear your heart on your sleeve.

I was asked to compile a list of the Top 5 Most Heartbreaking Songs of All Time. This is what I first came up with:

5. Maggot Brain by Funkadelic

4. The Jackson Song by Patti Smith

3. My Mummy’s Dead by John Lennon

2. Halloween Parade by Lou Reed

1. Nightswimming by R.E.M.

Serah-Marie asked me to elaborate, so I explained: Nightswimming seems to be about how the passage of time, even to the living, is analogous to death. Halloween Parade is about the early days of AIDS in Greenwich Village. My Mummy’s Dead is pretty self-explanatory (and the nursery-rhyme melody only underscores the misery). The Jackson Song is Patti Smith’s ode to her son & deceased husband. Maggot Brain is an instrumental meditation on George Clinton’s reaction to finding his dead brother’s remains weeks after he’d been shot through the head.

Serah-Marie pointed out that, although very sad, these weren’t really songs about heartbreak, they were heartbreaking songs about death. So here’s a list that Serah-Marie and I came up with together:

5. Eleanor Rigby by The Beatles
It doesn’t take a PhD in communications to recognize that this is a song about loneliness.

4. Heroes by David Bowie
Two lovers from opposite sides of the Berlin wall take their chances with the armed guards.

3. Don’cha Go Away Mad by Frank Sinatra
Guy gets caught cheating, and tries to placate his girl by half-heartedly acknowledging “you got a reason to be mad I suppose.” But she shouldn’t be mad because how was he to know that her cousin would be at the same restaurant? Entire self-help books would be written about this guy. And the girl doesn’t have a clue.

2. Everything by Connie Francis
Ms. Francis crossed over to country music in the mid-70s and given her thematic track-record, the move made complete sense: “Who’s Sorry Now?” “Breaking in a Brand-New Broken Heart” “Don’t Break the Heart that Loves You” “I Cried for You”

1. Everything by The Smiths/Morrissey
Like Connie Francis, Morrissey’s got the titles: “Why Can’t I Get What I Want” “Heaven Knows I’m Miserable Now” “Girlfriend in a Coma” and so on. But his lyrics push him into the number one spot: “There’s a club… but you leave on your own and you go home and you cry and you want to die.” “I will undoubtedly die alone,” etc.

This list is better, but I’m still not completely satisfied. What do you think are the most heartbreaking songs ever?

Your Host, Karaoke Ted.

THE SUPERMARKET, 268 Augusta Ave, Toronto
$7 at the door, $5 if you’re wearing RED

18 thoughts on “Bringin’ On the Heartbreak

  1. Similar to Connie Francis, anything by Patsy Cline (particularly ‘She’s got You’ which I must admit I got a bit weepy to yesterday).
    On a more silly note, might I add Michael Bolton’s ‘How am I supposed to live without you’ or Mariah Carey’s ‘Can’t Live (If living is without you)’ to the list?
    It seems I like to suggest the sad songs that are sad lyrically, but contextually make me laugh.
    My Therapist might call this displacement.

  2. Roy Orbison’s “Crying” (which is also one of the hardest karaoke songs KNOWN TO MAN). That part when his voice breaks in falsetto… yikes.

    I do agree with you on the Smiths (may even have to sing a song by them?

  3. You know, I always love when people sing in the style of another artist. You could always do “Crying” in a Morrissey voice. A friend of mine used to do a wicked Morrissey “Girls Just Wanna Have Fun.”

  4. “It Makes No Difference” by The Band. A countryish song about fatalistic heartbreak. Better live when they’re tired and run down by the drugs and the road.

  5. “The Ballad of Lucy Jordan” was always a sad one, but it gets exponentially sadder as I get older. Needless to say, I was very relieved to see Paris at 36.

    “At the age of thirty-seven she realised she’d never
    Ride through Paris in a sports car with the warm wind in her hair
    So she let the phone keep ringing as she sat there softly singing
    Pretty nursery rhymes she’d memorised in her daddy’s easy chair.”

  6. “Martha” by Tom Waits stabs me in the gut every time I hear it. “Love Will Tear Us Apart” is a painful disintegration dressed up as a dance song. “The Last Day of Our Acquaintance” by Sinead O’Connor isn’t much of a karaoke-friendly song, but just try not to relive every breakup you’ve ever had while you listen to it.

    Props to a lot of the previous suggestions; Patsy Cline was born to sing heartbreak songs, and “Crying” might be the ultimate heartache song ever penned. Good choices!

  7. this inspired me to make (another) heartbreak mix and pick 5 favorites to share (in no particular order):

    you swan, go on – mount eerie and julie doiron
    these two are masters of sad sad love songs. the whole lost wisdom album they did together is brilliant but this particular song always gets to me. i think it could be interpreted as a love song to oneself.

    hey that’s no way to say goodbye – leonard cohen
    another master of sad love songs. this was my first favorite leonard cohen song. ‘your hair upon the pillow, like a sleepy golden storm’ gets me every time!

    say yes – elliott smith
    all of his songs are extra sad to me since his tragic death. the line ‘situations get fucked up’ sums up pretty much every bad break-up ever though, but this at least ends a little hopefully.

    all my little words – the magnetic fields
    not even ‘all the tea in china’ could bring back this love. the vocal harmonies paired with stephin merritt’s suburb lyrical wit are crushing.

    just be simple – songs; ohia
    ‘why put a new address on the same old loneliness?’ jason molina’s smooth melting voice takes every sad sentiment and pours it deep into your heart.

    sad love songs are really my favorites :) and there are so many more!

  8. The live track ‘Restless Soul’ by Daniel Johnston is heartbreaking in a way that most songs are not.To be more specific: if your kind of heartbreak is listening to a tortured soul baring it all – and i do mean all, in a ‘I am a weeping mess, having meltdown in front of an audience of maybe 15 people BUT I WILL NOT STOP SINGING !!!’ sort of way.

    It is heartbreaking not so much in the vein of ‘a painting of a cute puppy dog in the rain with big sad eyes’ sort of way, more in the vein of ‘some please get this man some help!!”

    Guaranteed to clear the room, though, so I don’t suggest it for the Karaoke.

  9. I don’t know why but being dead seems to make your music extra heartbreaking.

    If someone managed to clear a room in a “get this man some help” kind of way at karaoke anywhere, I’d be really impressed.

  10. To name but a few:

    Ne Me Quitte Pas – Jacques Brel

    The Last One To Know – The Fleetwoods

    The Long Black Train – Lee Hazlewood (even if it is silly, and not about romantic heartbreak)

    Anything off Nick Drake’s Five Leaves Left, pretty much all of Dusty Springfield, and lots of The Kinks, who seem able to induce heartbreaking nostalgia in me if they catch me off guard.

  11. “Stay” by Hurts is a new one.. but worth the heartbreak.
    Brilliantly written, performed and sung (not to forget to mention drop dead gorgeous)

    My whole life waiting for the right time
    To tell you how I feel.
    Know I try to tell you that I need you.
    Here I am without you.
    I feel so lost but what can I do?
    ‘Cause I know this love seems real
    But I don’t know how to feel.

    We say goodbye in the pouring rain
    And I break down as you walk away.
    Stay, stay.
    ‘Cause all my life I felt this way
    But I could never find the words to say
    Stay, stay.

  12. not for karaoke, but “hello in there” by john prine. CRY CRY CRYYY

    party sounds phun tho! happy v-day serah-marie!!! (and everyone else! x0

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