I was listening to NPR in the car and I heard an interview with Tom Reynolds who put this book together, listing the 52 most depressing songs. I couldn't stop laughing because he was so spot on in his choices.

They played clips from Counting Crows (Round Here), Total Eclipse of the Heart, Hurt (the Johnny Cash version) and ragged on NIN and the Cure extensively. He's a bastard coated bastard, so he pretty much makes fun of everyone, but I found in intensely amusing. If you are goff, you will hate this. Just a heads up.

What are your go-to depressing songs?

Hear You Me - Jimmy Eat World.
Oh my god, I fucking sob.

Ray Lamontagne - All the wild horses

Saddest song ever.

NOT SAD. Depressing. Like, I can't get out of bed.

More importantly, BUY THAT BOOK
It's fucking hilarious. Best read ever. When he rips Evanescence a new one, it truly is better than Shakespeare, even when you consider what an easy target they are.

Few songs depress me, though the regularity with which some awful songs get played on the radio depresses me. I doubt it's the same thing. For example I don't find "Never had no one ever" by The Smiths depressing, because it's brilliant and I love it. On the other hand, I'm depressed every time I hear Jack fucking Johnson, despite the supposed levity of his material.