CHIRP: The Chicago Independent Radio Project

Tony Tschetter-Breed writes

Bum yourself out

Life can’t always be rocking out and feeling good. Sometimes you need a sad song. Here are a few songs then never fail to make me sad.

Sufjan Stevens – John Wayne Gacy, Jr.
Well, of course. Just about any song about a man who abused and killed teenaged boys would be sad, but Stevens did a really good job with this one.

Nina Simone – Strange Fruit
I know it’s a Billie Holiday song, but I like Nina Simone’s version better. When this song comes on I just have to stop whatever I’m doing and listen. For those who don’t know the song, it’s a vivid painting of the aftermath of a lynching.

James Taylor – Fire and Rain
It’s pretty easy to ignore this song when it’s on, but if you stop and really listen to the story, you’ll be sad for a day.

Jeff Buckley – Hallelujah
Buckley pulls every last drip of pathos out of this song. I like his version better than all others I’ve heard.

Johnny Cash and Fiona Apple – Bridge Over Troubled Water
Not a sad song, really, but there’s the power of the man in black.

The Streets – Dry Your Eyes
Should I be confessing that this song gets me every time? It feels like it doesn’t below on a list with these other songs; it’s just a song about a breakup. But something about the way he tells the story in real time, and puts you in the middle of it, makes you see and feel the pain of the moment.

What’s your favorite sad song?