11 Saddest Songs of All Time

These 11 saddest songs of all time will be a tough challenge for people that easily burst into tears. Music can move us in many ways, both positive and negative. Our mood is connected with our music preference. But that doesn’t necessarily mean that when we are sad we are going to play a happy song to cheer us up. Sometimes, listening sad songs can help us deal with the pain we feel.

JStone / Shutterstock.com 11 Saddest Songs of All Time

JStone / Shutterstock.com

Let’s be honest, all of us have locked ourselves, at least once, and mourned because of a love breakup, troubles in the family or at work, listening to a song that somehow captured our feelings and presented them in a shape of music.

It is probably hard to write a happy song while you are sad or lonely, and nothing brings you the joy. On the other side, you also can’t write a sad song if there is no sadness in your life. Emotions that music artists put in writing or performing a song are crucial for understanding the core of it and only if the interpretation of the song is equal to its message, we can feel it. Every songwriter has a thing that inspires him. While some seek inspiration in things that surround them, others find that same inspiration deep in themselves. If you seek some kind of inspiration, check out our 11 most inspirational songs of all time.

To find out our 11 saddest songs of all time, we used various pools like ones from Rolling Stone magazine and TheTopTens where people could vote for the saddest song for them, and lists like UpVenuePasteMagazine made by music journalists with addition from site dedicated to sad songs, WorldsSaddestSongs. We gave points to the each song based on their position, ultimately summing them up into our “sad count” and getting our list. 

11. Jeff Buckley – Hallelujah

Originally performed by Leonard Cohen, this song rose to popularity when Jeff Buckley covered it for his first and only album. The Buckley’s version is described as one with the most sorrow, which is understandable, considering Buckley’s early death.
Sad Count: 6


10. Roy Orbison – Crying

Song written by Orbison and Joe Melson eventually became a great hit for Orbison. When he wrote the song, he was inspired by an encounter with women that he still had feelings for.
Sad Count: 7


9. Harry Chapin – Cat’s in the Cradle

This song was originally written as a poem by Chapin’s wife Sandra, who draw the inspiration from the relationship between her first husband and his father. Chapin took the poem and rearranged it into a song that became his most successful work.
Sad Count: 8


8. Sinead O’Connor – Nothing Compares 2 U

Sinead O’Connor’s version of the song became one of the most known songs of the 90’s. A thing that most people don’t know about it is that this song was written by Prince for his side – project The Family but his version went unnoticed. The song tells the story about the lost love.
Sad Count: 9


7. Hank Williams – I’m So Lonesome I Could Cry

Initially, this song wasn’t meant to be sung. Hank Williams had the idea of speaking it on the record and in live performances, but later changed his mind. The theme of the song is loneliness, and it was inspired by Williams’s troubles in the relationship with his wife.
Sad Count: 10

6. Gary Jules – Mad World

The song was originally released by the British band Tears for Fears, but became popular worldwide when Gary Jules recorded his much slower and darker version. Melancholic tone of the song earned it the 6th place among saddest songs of all time.
Sad Count: 11


5. The Beatles – Yesterday

One of the most melancholic Beatles’ song talks about a sudden breakup. According to McCartney he got the melody of the song in his dream, and later was concerned that he may have heard it somewhere. “Yesterday” is one of the most covered songs in the history of music, with count till now being more than 2,200 times.
Sad Count: 11


4. George Jones – He Stopped Loving Her Today

Described as one of the greatest country songs, “He Stopped Loving Her Today” is a sad and depressive song about a man who never gave up on his love and continues to hope for a second chance. The moment he stopped loving her was the moment when he died.
Sad Count: 19

3. REM – Everybody Hurts

A major portion of this song was written by REM’s drummer Bill Berry, who later left the band to become a farmer. It is mostly conceived for teenagers who had a hard time to blend in and felt alone in the world. One of the interpretations is that this is anti – suicide song.
Sad Count: 27


2. Eric Clapton – Tears in Heaven

Described as one of the saddest songs in the history of rock music. Eric Clapton wrote “Tears in Heaven” after the death of his 4-year-old son who fell from a window of a 53rd-floor apartment in New York in 1991. After the event, Eric Clapton went into isolation, and he said that the music helped him overcome his pain.
Sad Count: 30


1. Nine Inch Nails | Johnny Cash – Hurt

It looks like this song is the favorite for all the sad people out there and tops our 11 Saddest Songs of All Time list. There are many different views on the meaning of this song. Featured are the themes of drug addiction, depression, and pain. Some even say that this song is similar to the suicide note.
Sad Count: 39