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The 10 Most Depressing Songs I've Ever Heard

November 14, 2011 by Somebody

WARNING: If you enjoy being happy, DO NOT listen to any of the following songs. They will surely send you plunging into the abyss of despair, where you might attempt to do dangerous and unpredictable things like juggling butcher knives while roller skating through rush hour traffic in downtown Los Angeles. See, here at this website, we care about our visitors and want you to have a long and happy life. Now that the disclaimer is out of the way, grab a box of Kleenex and read on if you dare.

10. "Fire and Rain" - James Taylor

"Sweet dreams and flying machines in pieces on the ground." I actually like this song a lot, and I used to think it would be cool if somebody recorded a heavy grunge-rock version of it. Or maybe Mr. Taylor himself could give it a try? Come to think of it, an album of heavy metal remakes might give his career the boost that it probably needs right about now. Just kidding, James. I know your fans would consider that an act of high treason.

9. "Pennyroyal Tea" - Nirvana

A strange and disturbing dirge about a type of herbal tea which is used to induce the abortion of an unwanted pregnancy, a subject which Mr. Cobain skillfully uses as a metaphor for self-loathing and suicide. Come on Kurt, cheer up a little. Life couldn't be that bad, could it? Wait a minute, how come you're not moving?

8. "The Great Gig in the Sky" - Pink Floyd

This beautiful instrumental from the Floyd's Dark Side of the Moon album features the legendary wordless vocal performance of Clare Torry. Rarely has so much bittersweet emotion been captured in a piece of recorded music. In context with the rest of the album, this song represents the end result of a life spent "kicking around on a piece of ground in your home town, waiting for someone or something to show you the way."

7. "Any Other Way" - The Posies

At first listen, this song from The Posies' excellent album Dear 23, which features the band's airy vocal harmonies and richly layered guitar, sounds like a pretty straightforward pop song. The lyrics, however, make for a fatally strong brew of post-breakup bitterness: "She left me alone, claiming we'd run out of things to fight about. I was crushed, of course, but at least I've something I can write about."

6. "Brick" - Ben Folds Five

"Now that I've found someone, I'm feeling more alone than I ever have before." For me, this song perfectly embodies the hopelessness of being in a bad relationship. As the piano slowly plunks out a remorseful melody, Ben describes a trip he took to an abortion clinic with his girlfriend the day after Christmas. He then compares her to a large brick, which is presumably tied to his ankle and is dragging him down to the bottom of the ocean.

5. "Powderfinger" - Neil Young

Neil could win a lifetime achievement award for depressing music, but this particular song makes stepping in front of an 18-wheeler seem like a pretty good decision. It recounts the bleak tale of a country boy who attempts to protect his kinfolk's land from hostile invaders. I have often tried to discern some kind of deep message within this grim little tune, but all I can come up with is: "Life sucks, and then you die."

4. "Long, Long Time" - Linda Ronstadt

Another song about a painful breakup. Linda sings with haunting intensity in this beautiful-but-sad tune from 1970, complete with swirling strings, mellotron and harpsichord. "I've done everything I know to try and change your mind, and I think I'm going to miss you for a long, long time." This was obviously written before the invention of Facebook.

3. "Hurt" - Nine Inch Nails

"I hurt myself today to see if I still feel. I focus on the pain, the only thing that's real." I have to admit, there was a time when I could relate to this self-pity anthem by the master of misery, Trent Reznor. I'm guessing he penned this beauty after coming down from a heavy drug binge. This song is so depressing that country legend Johnny Cash couldn't resist recording his own version of it.

2. "Ode to Billie Joe" - Bobby Gentry

Boy meets girl. Boy and girl fall in love. Girl leaves boy. Boy jumps off a bridge. Girl writes a really depressing song about it. Actually, I'm not sure if Ms. Gentry wrote this song, but she sings it as if she had been there in person.

1. "Ruby, Don't Take Your Love to Town" - Kenny Rogers

In which a paralyzed Vietnam veteran pleads with his wife to stop cheating on him. The final verse packs a wallop: "She's leaving now 'cause I just heard the slamming of the door, the way I know I've heard it slam one hundred times before. If I could move I'd get my gun and put her in the ground. Ruby, don't take your love to town." Kenny Rogers has two great claims to fame. One, he cooks some really good chicken. Two, he recorded the most depressing song of all time. Congratulations, Kenny. Through the power of your music, millions have been inspired to drink themselves into a coma.

"Won't you tell me where my country lies?" said the unifaun to his true love's eyes...