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