10 Very Sad Songs That Make You Cry

Get a box of tissues and get ready for a weep-fest with our list of 10 very sad songs that make you cry. Whether you’re having a bad day or suffering from the pangs of heartbreak, these 10 sad songs are there to help you let it all out by expressing all of the things that you may not be able to say.

1. "Hurt," Nine Inch Nails, 1994; Johnny Cash, 2002. This song is gut-wrenching. The original NIN version is tinged with the sadness and guilt of addiction, while the Johnny Cash cover is drenched in the sorry of a man who seems to know the end is nigh and he needs to say good-bye. It’s this intense sadness that makes this very sad song very likely to make you cry.
2. "All Cried Out," Lisa Lisa and Cult Jam, featuring Full Force, 1985. Listening to Lisa Lisa pour her heart out as she says good-bye to her wayward lover always brings a tear to our eyes. It’s a great, very sad break-up song that makes you cry because you know Lisa Lisa knows what you’re going through.
3. "Stan," Eminem, 2000. This makes our list because it makes us sad and scares the crap out of us at the same time. Maybe we have had one too many stalkers around the office, but we always imagine it could be us in that trunk.
4. "Mad World," Tears for Fears, 1982; Gary Jules, 2003. If this sad song doesn't make you cry, you have no soul. Don’t let the soft syth-pop sounds of the original fool you, this is a song about the the pain of being displaced in the world. It’s the slowed-down cover version that really drives home the sorrow and makes you want to crawl into a hole and cry.
5. "There’s a Light that Never Goes Out," The Smiths, 1986. This is another very sad song that is sure to make you cry. It uses a combination of fear and loathing to make you misty. The thought of being so miserable that you would rather get hit by a bus with the one you love than live alone is a heavy one indeed.
6. "Never Is a Promise," Fiona Apple, 1996. Raw vulnerability is what makes this sad song a tear-jerker. This song has it all: shame, fear and sadness, with an undercurrent of the kind of strength that comes from people who are looking looking to find their voice. Someone hand us a tissue!
7. "Silent All These Years," Tori Amos, 1992. In many ways this song is Tori Amos’ life story. It details her sexual abuse as a young woman and how she survived abusive relationships. Thinking about all of the things that happened to her to inspire this song makes it one very sad offering.
8. "This Used to Be My Playground," Madonna, 1992. This very sad song makes our list because it tells two equally sad stories, depending on who is listening to it. On the one hand it’s a woman mourning for her lost youth, and on the other had it could be about a woman coming to terms with the aftermath of abuse. Any way you slice it, this is a touching song that will make you cry.
9. "One More Try," George Michael, 1988. We had to put this on our list because it is the ultimate break-up song. It’s everything that happens in a relationship when one person wants out and the other doesn’t want to drop it.
10. "La Vie en Rose," Edith Piaf, 1946; Grace Jones, 1977. It isn’t the lyrics that make you cry with this sad song. It’s the subtle sadness and forced optimism.