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Cops O: Manic Monday

The Top 11 Most Depressing Songs of All Time

by dsussman   January 29, 2009 at 10:00AM  |  Views: 847,089

There’s just something about a depressing song that can instantly shift your mood from light to dark. A lot of music listeners out there will even use gloomy and emotional songs to put themselves in a low-spirited state. If you're one of those people, these are the songs most likely to make you want to wallow in the darkness.

Photo: Gemma Levine / Hulton Archive / Getty Images

By Dustin Sussman

The following article does not represent the opinions of Spike TV or its affiliates.


11. “Yesterday” - The Beatles


Photo: Michael Ochs Archives/Getty Images

This melancholy 1965 ballad about a serious breakup can put any heartbroken lover into a deeper funk than heroin addiction. The combination of Paul’s soothing vocals and a solid string quartet give “Yesterday” a simplistic brilliance that only a Beatle could pull off.

Not only is this song in the Guinness Book of Records for having the most cover versions of any song ever written, I’m also guessing that its been used in more Bar Mitzvah videos than Rod Stewart’s “Forever Young.”

My Nana loved this song.

10. “Mad World” - Gary Jules Version

Who couldn’t connect with a song about looking out at an insane world from the eyes of a young adult? And if that wasn’t enough to get suicidal thoughts running through your mind, composers Michael Andrews and Gary Jules somehow went ahead and made it even more dark and dreary than the Tears For Fears original.

I’m assuming the first time anyone heard this song at the end of Donnie Darko they ran to their local record store in a hurry for another fix. Listening to the sounds of a dreamy piano mixed with Jules’ adolescent-like vocal chops is a perfect way to help a dark moment last just a little bit longer.

9. “untitled 1 (a.k.a. Vaka)” - Sigur Ros

Some of you may not know this song and it might be a good idea to keep it that way. I made the mistake of watching this music video at work and I totally got caught by my boss tearing up in my cubicle. Burn.

Since day one, the Icelandic indie superstars have had a way with making music that invokes uncontrollable emotions from their listeners. With “untitled 1,” the band definitely made cups overflow with fresh hipster tears all around the world. The song’s ambient sounds and falsetto vocals are one of a kind and seem to have an intense reaction with its diehard listeners.

To be able to choke up a listener 5 seconds into a song is a pretty amazing task if you ask me.

8. “Sleepwalk” - Santo & Johnny

For most of us, this 1959 classic from the Italian-American Brooklyn duo is etched in our minds due to the dramatic ending of La Bamba when Ritchie Valens' brother Bob screams Ritchie's name up to the heavens. It seemed to be an extremely emotional moment that was heightened with the use of this steel guitar-based landmark.

Santo’s steel guitar playing on this track is also pretty timeless. Right when the first note drops, anyone in a 10-yard radius seems to melt into a puddle of sentimental goo. Their minds instantly travel back to the most epic days of their youth.

7. "How To Disappear Completely" - Radiohead


Photo: Jim Steinfeldt / Getty Images

There are seriously so many depressing Radiohead tracks to choose from, but I’ve always thought that this one took the cake.

When Kid A was released back in 2000, I remember this song having some kind of odd power over the ladies. They got so choked up and sentimental anytime it came on. Even if they were in the greatest if moods, “How to Disappear Completely” could put a serious damper on any situation.

6. “Strange Fruit” - Billie Holiday

This list would not be complete without some Billie. The thing that separates Billie Holliday from other run-of-the-mill singers is the fact that you can actually feel the pain with every note she releases from her body.

With "Strange Fruit," Billie condemns American racism and addresses the lynching of African Americans in the South. When you hear her singing lines about bodies of African American men being hanged during a lynching, you can’t help but be moved every single time.