10 Best Sad Depressing Songs

If you’re in a good mood and hating every minute of it, these 10 best sad, depressing songs should paradoxically cheer you right up. Enjoy your misery, you sad sack.

  1. “Mad World” by Gary Jules. Skip the original Tears for Fears version and go straight for the Gary Jules cover. This song was the second most memorable thing about the movie “Donnie Darko,” right after the guy in the bunny costume. It’s also quite a downer.
  2. “Padraic My Prince” by Bright Eyes. How does a song about a baby dying in a bathtub sound to you? Pretty depressing? Man, it sure is. Conor Oberst wrote some of the saddest songs you’d ever hope to hear before he decided he was the next Bob Dylan and went all folksy troubadour on us. This song was the pinnacle of what we’ll call his “misery period.”
  3. “Summer Skin” by Death Cab for Cutie. Ben Gibbard has written quite a few sad, depressing songs about lost love, and this is among his saddest. The lyrics draw a parallel between the end of summer and the end of a relationship. Personally, we don’t like either of those things.
  4. “O’Rourke’s, 1:20 A.M.” by The Good Life. A band called The Good Life that has yet to release even a moderately upbeat song? Oh those hipsters and their irony. You can pretty much pull up any song from The Good Life on your iPod and be guaranteed an instant buzzkill. This song about feeling alone among the last remaining stragglers of the night down at the local bar is no exception.
  5. “Half Right” by Elliott Smith. Elliott Smith was a troubled soul. Long troubled by depression and heroin addiction, he ultimately ended up dying from apparently self-inflicted stab wounds. That makes the self-loathing lyrics of “Half Right” all the more difficult to listen to. It is a genuinely sad song by a genuinely sad person.
  6. “Sylvia” by The Antlers. Given the title, it’s no surprise that the Antlers’ debut album “Hospice” is a rather unhappy affair. Following the troubled relationship between a man and his cancer-stricken lover, there is nary a bright spot to be found. Case in point:  “Sylvia,” a song that references poetess Sylvia Plath. Plath, you see, died by sticking her head in an oven until the gas fumes overwhelmed her.
  7. “Flume” by Bon Iver. It’s certainly not shocking that an album written in isolation in a cabin in the woods during the winter would come out a bit melancholy. Bon Iver’s amazing debut, “For Emma, Forever Ago,” is equal parts beautiful and mournful. “Flume” is one of its standout tracks.
  8. “How to Disappear Completely” by Radiohead. It’s an ironic song title for a band that has managed to stay relevant for the better part of two decades now.  Still, “How to Disappear Completely” is one of the more sad, depressing songs Radiohead have released. It dials down much of the electronic noisiness of the rest of “Kid A” in favor of an acoustic guitar and Thom Yorke’s plaintive, haunting voice.
  9. “Death Take Your Fiddle” by Spiritualized. That sound you hear in the background of this song is lead singer Jason Pierce breathing through a machine after a serious illness nearly killed him. Much of the album “Songs in the Key of A&E” sounds like a celebration of life, but this track is a solemn reflection on a brush with death.
  10. “Limousine (MS Rebridge)” by Brand New. This sad, depressing song is based on the true story of a little girl who was killed by a drunk driver on the day she was to be a flower girl at her aunt’s wedding. When the police arrived on the scene, the girl’s mother was cradling her daughter’s severed head in her arms. If that story doesn’t absolutely ruin your day, you need to get your heart examined.
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