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Valentimes Can Be Sad Times

February 14, 2011

Hey, today is Valentines Day! Perhaps you’d forgotten? So how about a selection of the top five most depressing breakup songs I could think of? Okay!

5. “Total Eclipse of the Heart” – Bonnie Tyler

The HR lady in your office has had too much wine and belts this out unprompted at your next work-related social event. No one knows what to do.

4. “Left & Leaving” – The Weakerthans

That moment when you know it’s over for good. Also, sad wolf is sad.

3. “Good Year for the Roses” – Elvis Costello

A couple of boyfriends ago, we observed the Halmarkiest of holidays by hanging out in his living room and drinking cheap whiskey. Probably Royal Reserve. This was hindered by his next door neighbour who insisted on playing this song on repeat all night, more than loudly enough for me to identify it as it seeped through the walls. Prior to this I hadn’t noticed that it was in fact a heart-wrenching tale of that part of the breakup where you have to go back and pick up the last of your stuff and not a song about actual roses. The hubris and naiveté of youth, ladies and gentlemen.

Bonus George Jones original:

2. “Love Will Tear Us Apart” – Hawksley Workman

I don’t like anything else I’ve heard by Hawksely Workman. Furthermore, I’d like to impose a world-wide moratorium on bands covering this song (go fuck yourselves, Fallout Boy), but I think I actually prefer this to the original. It’s somehow both sadder and less bitter, but with a depressed resoluteness about it which the original lacks. Indeed, love will tear us apart.

Listen on GrooveShark, because I couldn’t find one single video for this song.

1. “Time After Time” – Cyndi Lauper

I literally can’t listen to this whole song without crying. I’ve been out shopping and had it come on in the store and then had to leave immediately. It’s the video. It’s got you missing your mom. Remembering the good times but knowing you have to leave. Getting on the train even when he asks you to stay. The. Worst.

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