The 20 Best Sad Songs Of All Time (In 2016-2017)

Whether you’re going through a difficult breakup, dealing with the loss of a loved one, or experiencing pain or sadness in some other form, listening to a painfully sad and depressing song is something that many people seek out in times of need. No matter the reason for throwing on a tearjerker of a tune, the top 20 songs below are guaranteed to tug at your heartstrings.
1. The Beatles – Yesterday

A simple, somber tune, “Yesterday” features the melancholy vocals of Paul McCartney reminiscing about a love past. There is a reason this is one of the most popular songs by the Beatles.

2. John Legend – All of Me

A song about unconditional love, “All of Me” is the perfect listen for those times when you’ve messed up and done something wrong.

3. Joy Division – Love Will Tear Us Apart

Seriously though, it doesn’t get much sadder than “Love Will Tear Us Apart.” It’s more than just your standard breakup song. Instead, it’s a heart wrenching ballad that chronicles the fragility of human emotions and the bittersweet nostalgia of watching something you truly love go to waste.
4. Amy Winehouse – Wakeup Alone

Loneliness is one of the most powerful emotions in the human experience. Amy Winehouse captures this feeling of loneliness perfectly in “Wakeup Alone.”
5. Modest Mouse – Little Motel

A song about the unavoidable reality that is death, “Little Motel” is a somber tune any way that you look at it. Yet it is able to remain surprisingly tender and gentle.
6. Adele – Someone Like You

This song is uniquely paradoxical in that it is Adele’s rejection of sadness and refusal to cry that actually causes it to be such a tearjerker for her audience.
7. Daughter – Youth

There is no shortage of sad songs described as haunting and beautiful. But “Youth” by Daughter is truly one of them. Be sure not to play this one unless you’re actually looking to cry – because you will.
8. Rihanna – Stay

The power of this song is in the struggle that the singer feels in her relationship. She chooses to stay even when she knows it is best to go. It is a very sad song that hones in on the vulnerability we often experience in relationships.

9. Jimmy Ruffin – What Becomes of the Brokenhearted

Another classic breakup song, “What Becomes of the Brokenhearted” asks this soul twisting question over and over again. So what does become of the brokenhearted

10. Kanye West – Say You Will

Kanye West might not be the first artist you think of when you think of sad songs. But “Say You Will” from his reflective album 808 & Heartbreak shows Kanye at his most vulnerable. It is a raw rumination on the confusing emotional complications that often result from a difficult breakup.
11. Elton John – Your Song

Almost everyone has experienced the heartbreak that is unrequited love. And Elton John perfectly captures the emotion that is loving someone that doesn’t love you back in his hit “Your Song.”
12. Cyndi Lauper – Time After Time

This is a sad song that will almost assuredly prompt you to ask “what if?” It’s the kind of song that makes you think of all those loves gone by and all those missed moments.
13. Gary Jules – Mad World

When its melancholy you want, it’s melancholy you’re going to get when you listen to “Mad World” by Gary Jules. A stripped down cover that appeared in the film Donnie Darko, the song was originally written and performed by Tears for Fears.
14. Johnny Cash – Hurt

Another cover, Johnny Cash’s rendition of “Hurt” takes the hit song by Nine Inch Nails and peels away a few layers for a simpler, stripped down, some say rawer feel.
15. The Cure – From the Edge of the Deep Green Sea

Robert Smith of The Cure has always been known as one of the top writers of sad songs in the world. And his “From the Edge of the Deep Green Sea” does not disappoint. The heartbreaking lyrics discuss the idea of finding a love and then realizing it won’t last forever based on your past.
16. Nine Inch Nails – Hurt

Yes, we already mentioned Johnny Cash’s cover of “Hurt,” but the Nine Inch Nails original is right up there as well. The band’s most popular song, the depressing ballad touches on a number of subjects ranging from drug abuse to suicidal thoughts to deep emotional pain. If you want a darkly depressing sad song, then this one is for you.

17. The Smiths – Please, Please, Please, Let Me Get What I Want

In his heyday as lead singer for The Smiths, the legend that is Morrissey was known as one of the darkest, moodiest vocalists around. In fact, the band’s hit song “Please, Please, Please, Let Me Get What I Want” is still considered one of the most depressing of all time. It examines the feelings of helplessness and despair that are often experienced by the heartbroken.
18. Luther Vandross – Dance With My Father

There aren’t enough songs out there made about parents. “Dance With My Father” by Luther Vandross is one of the best. It’s a touching song that makes you think about and remember all that your parents have done for you.
19. Eminem – Difficult

With a simple, straightforward beat, “Difficult” by Eminem strips away the excess and lets you focus on the words. It is a song that deals with despair, loneliness, and the loss of a loved one.
20. Eric Clapton – Tears in Heaven

Undoubtedly one of the saddest songs of all time, “Tears in Heaven” was written shortly after the tragic death of Eric Clapton’s four year-old son Conor. It finds the singer imagining that he could just spend just a little more time with his little boy. These 20 best sad songs are sure to give you a good cry and make you think. Whatever your reason for listening to a sad song, these ones will help you get through whatever you’re going through.

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