These are By Far, the Saddest Songs You’ve Ever Heard

Do ever notice that when you’re feeling down, all you want to do is listen to sad music all day? Well, this list can support your blue mood next time it happens. These are the 40 saddest songs of all time, based on Rolling Stone and other rankings. We would say enjoy, but that’s probably not the best word. So we’ll just say… here you go. And you’re welcome.

Oh and don’t forget to check out our custom-made playlist at the end!

40. U2 – Kite

“Who’s to know when the time’s come around / Don’t want to see you cry / I know that this is not goodbye”

Bono wrote this song after flying a kite with his two daughters. But the song was written for his father, Bob Hewson, who died of cancer on August 21, 2001. U2 played a concert in London just a few hours after his father’s death and Bono dedicated this song to him.

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The incident with the kite brought Bono back to his childhood when his father flew a kite with him. Bono said of the song: “I wasn’t sure of my own well-being. I just wanted to have some songs that would, in a way, tell my kids something about who their father was.”

39. Bob Dylan – Knockin’ on Heaven’s Door

“Mama, put my guns in the ground / I can’t shoot them anymore / That long black cloud is comin’ down / I feel I’m knockin’ on heaven’s door”

Bob Dylan’s song describes the feelings and impressions of a dying deputy who is not going to continue his role as a law enforcer. A cover version of his song was also sad.

Mama, put my guns in the ground, I can’t shoot them anymore, That long black cloud is comin’ down, I feel I’m knockin’ on heaven’s door

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In 1996, Dylan gave Scottish musician Ted Christopher the green light to record a new verse for the song which Christopher wrote in memory of the schoolchildren and teacher killed in the Dunblane massacre. This was a very occasion in which Dylan officially permitted someone to add to or change the lyrics to one of his songs.

The next song was played at every graduation ever since it came out.

38. Green Day – Good Riddance (Time of Your Life)

“For what it’s worth, it was worth all the while / It’s something unpredictable, but in the end it’s right / I hope you had the time of your life”

This song is a huge favorite at graduation ceremonies because of its sentimental quality but it’s actually about a break-up. Billie Joe Armstrong, the band’s frontman, explained the meaning of the song…

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“At the time I wrote Good Riddance, I was breaking up with a girl that was moving to Ecuador, and I was trying to be as understanding about it as I could. I wrote the song as kind of a bon voyage. I was trying not to be bitter, but I think it came out a little bit bitter anyway… I thought that calling the song “Time of Your Life” was just a little too level-headed for me, so I had to come up with something different.”

37. Elton John – Candle in the Wind

“And I would have liked to have known you / But I was just a kid / Your candle burned out long before / Your legend ever did”

Elton John rewrote and re-recorded his original 1973 version of Candle in the Wind which was a tribute to Marilyn Monroe. He then rereleased the song as a tribute to the late Princess Diana. When she was killed in a car crash in Paris in 1997, John entered into a deep depression.

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Elton John performed Candle in the Wind 1997 only once, at the funeral in Westminster Abbey on September 6, 1997. He still sings the original 1973 version of the song at his concerts, but repeatedly turns down requests to perform his 1997 version. Apparently, he vowed never to perform the song again unless Diana’s songs ask him to.

The next sad tune is a Leonard Cohen original.

36. Jeff Buckley – Hallelujah

“Maybe there’s a God above / But all I’ve ever learned from love / Was how to shoot somebody who outdrew ya”

Hallelujah was written by Leonard Cohen but the cover is by Jeff Buckle. And his version of the song is more mournful than the Cohen’s.

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The song is about love that has gone stale. Cohen, in his lyrics, used a lot of religious imagery, with references to notorious women in the bible. Cohen explained: “Hallelujah is a Hebrew word which means ‘Glory to the Lord.’ The song explains that many kinds of Hallelujahs do exist. I say: All the perfect and broken Hallelujahs have an equal value. It’s a desire to affirm my faith in life, not in some formal religious way but with enthusiasm, with emotion.”

35. Simon & Garfunkel – The Sound of Silence

“Hello darkness, my old friend / I’ve come to talk with you again”

The story goes that Paul Simon took six months to write the lyrics. And the song is about a man’s lack of communication with his fellow man in which he averaged one line a day.

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Contrary to what people think, Simon & Garfunkel didn’t write the song about the Vietnam War. But by the time it became popular, the war already started and people felt it made a powerful statement as an anti-war song.

Next up, David Bowie’s sad song. Do you know which one it is?

34. David Bowie – Space Oddity

“Though I’m past one hundred thousand miles / I’m feeling very still / And I think my spaceship knows which way to go / Tell my wife I love her very much she knows”

The song was written after Bowie saw Stanley Kubrick’s film 2001: A Space Odyssey. Bowie explained the song: “In England, it was always presumed that it was written about the space landing… But it actually wasn’t. It was written because of going to see the film 2001, which I found amazing.”

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“It got the song flowing. It was picked up by the British television and used as the background music for the landing itself. I’m sure they really weren’t listening to the lyric at all (laughs). It wasn’t a pleasant thing to juxtapose against a moon landing. Of course, I was overjoyed that they did. Obviously, some BBC official said, ‘Oh, right then, that space song, Major Tom, blah blah blah, that’ll be great.’ ‘Um, but he gets stranded in space, sir.’ Nobody had the heart to tell the producer that.”

33. Mike & the Mechanics – The Living Years

“I wasn’t there that morning / When my Father passed away / I didn’t get to tell him / All the things I had to say”

Mike Rutherford, the band’s frontman and a founding member of Genesis, said: “The lyrics were written by B.A. Robertson and the song is about something he went through. He lost his Dad and it’s about the lack of communication between him and his father before he died. There’s also the irony of him having a baby just after losing his father.”

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The song was actually written after Robertson’s father died which was 12 weeks before the birth of his own son.

The sad song that appears next on the list belongs to the Beatles. Which one do you think it is?

32. The Beatles – Eleanor Rigby

“Eleanor Rigby, died in the church / And was buried along with her name / Nobody came / Father McKenzie, wiping the dirt / From his hands as he walks from the grave / No one was saved”

Paul McCartney wrote the eerie yet brilliant tune. He wasn’t sure what the song was going to be about until he came up with the line, “Picks up the rice in a church where a wedding has been.” He then came up with the story of an old, lonely woman. The lyrics, “Wearing the face that she keeps in a jar by the door” are a reference to the cream she puts on in an effort to look younger.

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First, we meet a churchgoing woman named Eleanor Rigby, and then we meet the pastor, Father McKenzie, whose sermons “no one will hear.”

31. Sarah McLachlan – Hold On

“So now you’re sleeping peaceful / I lie awake and pray / That you’ll be strong tomorrow / And will see another day”

Sarah McLachlan explained the meaning of Hold On: “It was from pure emotion. I was watching a documentary called a ‘Promise Kept’ it was made in Canada. It was about this woman who discovered her fiance was HIV positive and basically, the story followed her and her husband.”

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“They got married and he got progressively sicker and she took care of him right up until the end, and she was telling her story with just such, y’know, beautiful clarity and honesty and it just, it struck home in a way that I couldn’t really describe except by writing this song and I really feel like it’s something that came out of me through her.”

Bruce Springsteen is next on the list. Can you think of a sad song of his? Maybe it’s the one.

30. Bruce Springsteen – Streets of Philadelphia

“Night has fallen, I’m lyin’ awake / I can feel myself fading away / So receive me brother with your faithless kiss / Or will we leave each other alone like this / On the streets of Philadelphia.”

The song was made for the 1993 film Philadelphia, which was the first mainstream film on HIV/AIDS. It was inspired by the story of Geoffrey Bowers, a lawyer who in 1987 sued the law firm Baker & McKenzie for wrongful dismissal in one of the first AIDS discrimination cases.

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Bruce started writing the song based on lyrics he already wrote about the death of one of his friends. The director of the movie heard the song and loved it, feeling it was perfect for his movie.

29. A Great Big World Feat. Christina Aguilera – Say Something

“Say something, I’m giving up on you / I’m sorry that I couldn’t get to you / Anywhere, I would’ve followed you / Say something, I’m giving up on you”

When the song was released, it was hardly noticed at all. It was a different version, not the one we know today. Then one night, on an episode of So You Think You Can Dance in 2013, Amy Yakima used the song during her performance.

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After that episode, the song blew up and two months later, Christina Aguilera rerecorded the lyrics and transformed the song into the version we all know today.

Remember Luther Vandross? His song is a real tear-jerker.

28. Luther Vandross – Dance With My Father

“I know I’m praying for much to much / But could you send her / The only man she loved / I know you don’t do it usually / But Dear Lord / She’s dying to dance with my father again”

Luthor Vandorss’ last album, Dance with My Father, was his last album released before his death on July 1, 2005. He wrote this song after he suffered a stroke that eventually killed him two years later.

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The song is about Vandross’ late father who died when he was young, and Luther’s most touching memory of his dad was him dancing in the house with his kids. Hence, where the concept of “Dance With My Father” came from.

27. Passenger – Let Her Go

“You see her when you close your eyes / Maybe one day you’ll understand why / Everything you touch surely dies”

Mike Rosenberg explained the song’s meaning: “In my mind, the song has two meanings;” he said, “the first is quite literal as I wrote it after a break-up and it is about letting her go.”

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“But then there is a bigger idea going on and is more about not really understanding and knowing what you have until it is gone and I think everyone can definitely relate to.”

You’ll definitely remember the next song on this list.

26. Sinead O’Connor – Nothing Compares 2 U

“All the flowers that you planted mama / In the back yard / All died when you went away”

This song’s original version is by Prince, but O’Connor’s cover gained a much larger audience. Based on polls and surveys, this song has made grown men cry. So it’s not just for the ladies.

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O’Connor has stated that she hated the fame the song brought her, struggling with the new commercialization of her music. She earned a Grammy for Best Alternative Performance, but she refused to appear as a protest of materialism in the music industry.

25. Toni Braxton – Unbreak My Heart

“Un-break my heart / Say you’ll love me again / Undo this hurt you caused / When you walked out the door”

This is a song of heartbreak, as she’s singing to her former lover. She begs him to come back to her and take away all the pain he caused her. Diane Warren, the songwriter, was surprised the phrase “Un-Break My Heart” was never used as a song title before.

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Warren spoke of Toni and the song. She said: “Toni Braxton hated that song. She didn’t want to do it. And then after she had a hit with it she told me she didn’t want another one of those.”

24. Bonnie Tyler – Total Eclipse of the Heart

“Once upon a time I was falling in love / But now I’m only falling apart / And there’s nothing I can do / A total eclipse of the heart”

This song is about the all-consuming, and destructive love that is taking all the good out of her life. This can be seen in the lyrics: “Once upon a time I was falling in love, but now I’m only falling apart/There’s nothing I can do, a total eclipse of the heart.”

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The song was inspired by the novel “Wuthering Heights” where the relationship between Catherine and Heathcliff shared an intense, passionate love for each other. It was toxic and destructive.

23. Phil Collins – Another Day In Paradise

“She calls out to the man on the street / ‘Sir, can you help me? / It’s cold and I’ve nowhere to sleep / Is there somewhere you can tell me?’”

The lyrics of this song talk about the social problem of homelessness. He is telling the story of a random man on the street who ignores the suffering of a homeless woman. He acts as though he can’t hear her and crosses the street to avoid the sight.

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The lyrics then plead for people not to ignore the troubles of the homeless. The whole point of the song: for us, it’s just another day in paradise, but for them, this isn’t the same.

22. Queen – Love Of My Life

“Love of my life, don’t leave me / You’ve stolen my love, you now desert me / Love of my life, can’t you see?”

This song is about a man who’s been abandoned by his lover. It describes how he feels as though it does him more harm than it does his lover.

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And he pleads, “Bring it back home to me because you don’t know what it means to me.” Since Freddie’s death in 1991, Brian May does the live vocals when he performs the song. Often at Queen shows, the audience sings a part of the song and May gets pretty emotional.

The next song is by a pop singer, but the song is truly sad.

21. Brad Paisley and Alison Krauss – Whiskey Lullaby

“We found her with her face down in the pillow / Clinging to his picture for dear life
We laid her next to him beneath the willow / While the angels sang a whiskey lullaby”

The duet is about a man and a woman who were married and then he went to war. But when he came back, she was with another man. So he kills himself, drinking himself to death, and left her a note to say that he still loves her.

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The wife then mourns his loss. She is ridden with guilt, thinking it’s her fault and eventually kills herself as well, drinking herself to death while holding his picture. How depressing!

Bonnie Raitt is next. Try to guess which song it is.

20. Bonnie Raitt – I Can’t Make You Love Me

“‘Cause I can’t make you love me if you don’t / You can’t make your heart feel something it won’t / Here in the dark, in these final hours / I will lay down my heart and I’ll feel the power”

The song is about a woman who knows her husband has lost interest and she wants one more night with him.

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Instead of lying to herself or trying to work things out, she confronts the reality and looks for closure with that final night together. In the morning, she plans on leaving. The song was covered by many artists, including Prince, Boyz II Men, Adele, and George Michael.

19. Counting Crows – Round Here

“I can’t see nothing, nothing round here (oh) / Won’t you catch me if I’m falling? / Won’t you catch me if I’m falling? / Won’t you catch me ’cause I’m falling down on you.”

Lead singer Adam Duritz said the song is about him. “The song begins with a guy walking out the front door of his house and leaving behind this woman. But the more he begins to leave people behind in his life, the more he feels like he’s leaving himself behind as well, and the less substantial he feels about himself.”

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“That’s sort of what the song’s about: even as he disappears from the lives of people, he’s disappearing more and more from his own life.”

The next song is one of the singer’s best-known hits.

18. Jewel – Foolish Games

“Well in case you failed to notice / In case you failed to see / This is my heart bleeding before you / This is me down on my knees”

This is a song about the frustration of unrequited love. Her inspiration for the song was a guy Jewel fell for when she was 16. She actually wrote about him in her diary, which ended up becoming a relationship on its own, as she said, “dramatically involved in on paper.”

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Her diary accounts turned into a poem, and a year later she turned it into a song. Who would have thought that teenage diary pages can turn into hit singles?

17. Johnny Cash – Hurt

“What have I become / My sweetest friend / Everyone I know / Goes away in the end”

Six months after Cash released his final album, his wife, June Carter Cash, died. And four months later, he passed away. The song is Cash’s rendition of Nine Inch Nails’ “Hurt.”

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“I hurt myself today/ to see if I still feel,” … “What have I become, my sweetest friend?/ Everyone I know goes away in the end.” The original song has been interpreted as a suicide note. In Cash’s case, it was more of a death-bed memoir.

Our next artist may not come as a surprise as most of her music is sad.

16. Adele – Someone Like You

“Never mind I’ll find someone like you / I wish nothing but the best for you too
Don’t forget me I beg, I’ll remember you said / Sometimes it lasts in love but sometimes it hurts instead”

Almost all of Adele’s songs are full of heartbreak. After she first performed the song, she said: “I was really emotional by the end because I’m quite overwhelmed by everything anyway, and then I had a vision of my ex, of him watching me at home and he’s going to be laughing at me because he knows I’m crying because of him, with him thinking, ‘Yep, she’s still wrapped around my finger.’”

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When asked how she felt inspired for the song, she said: “I was trying to remember how it was I felt at the beginning of a relationship,” she said. “Because as bad as a break up can be, as bitter and horrible and messy as it can be, that feeling when you first fall for someone is the best feeling on earth, and I am addicted to that feeling.”

15. Mariah Carey – My All

“I’d give my all to have / Just one more night with you / I’d risk my life to feel / Your body next to mine”

Mariah considered this period in time to be a “redefining moment for herself,” and she expressed how the mixed emotions she felt then helped develop this song.

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Carey said that her visit to Puerto Rico inspired her to write the song. She said “When I came back, the melody was in my head. It was at a melancholy point in my life and the song reflects the yearning that was going on inside of me. It was like being in a situation but you want to break free and you can’t, so you’re confined yet you’re releasing those emotions through the lyrics and the actual act of singing. That’s why think a lot of people felt very strongly about that song because the emotion is clear when you listen to it.

14. Skeeter Davis – It’s the End of the World

“Why does my heart go on beating? / Why do these eyes of mine cry? / Don’t they know it’s the end of the world? / It ended when you said goodbye”

“The End of the World” is a sad song about a romantic breakup. Dee, the lyricist, took inspiration from her father’s death to set the mood for the song.

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You might know the cover version by the Carpenters which was released I 1975.

The next song is from Donnie Darko. Can you guess which one?

13. Gary Jules – Mad World

“And I find it kinda funny, I find it kinda sad / The dreams in which I’m dying are the best I’ve ever had”

This is actually a remake of the 1982 Tears For Fears original. And then Gary Jules and Michael Andrews covered it for the movie soundtrack for Donnie Darko in 2001.

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“Mad World” builds a very dark scene of normal situations, like birthday parties and school classes. The entire piece puts you in a very deep trance.

Pink Floyd is next on the list. Have you heard the song?

12. Pink Floyd – Wish You Were Here

“How I wish How I wish you were here / We’re just two lost souls Swimming in a fish bowl”

The song is about that feeling of detachment that people feel throughout their lives.

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Roger Waters wrote the song about coping with the world by withdrawing physically, mentally, and emotionally. Waters stated that the inspiration was the band’s founding member, Syd Barrett, and dealing with his schizophrenia.

11. Amy Winehouse – Back to Black

“We only said goodbye with words / I died a hundred times / You go back to her
And I go back to / I go back to us”

Amy’s music was always full of soul and sadness. And this one was about a painful breakup. Her song sums it all up in one line: “I died a hundred times.”

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Sadly, Amy died of alcohol poisoning in 2011, at the young age of 27.

Next up: a sad as ever country song. You probably heard of it.

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

“The silence of a falling star / Lights up a purple sky / And as I wonder where you are / I’m so lonesome I could cry”

Three years before he died, Hank Williams wrote this song as a self-expressive piece about failing marriage to his wife Audrey Sheppard.

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The fame of this song is unsurprising as many can relate to his pain. It’s been covered by many artists, from Elvis Presley to Johnny Cash.

9. Alice in Chains – Nutshell

“And yet I find / Repeating in my head / If I can’t be my own / I’d feel better dead”

After singer Layne Staley died tragically at a young age, this song took a whole new meaning. Listening to the song knowing of his death, lyrics like “I’d feel better dead” can send a chill down your spine.

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The next song involves a war vet. Bonus points if you guess the song. It’s by John…

8. The Smiths – I Know It’s Over

“But not for such as you and I, my love / Oh Mother, I can feel the soil falling over my head”

This song is about a dying man reflecting on his wasted and lonely life. This song was written one evening and the band members explained: “We recorded it around about teatime, but England being England it was dark and wet outside.”

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“It was very beautiful and it reflected how I felt for a large part of my life, and particularly during that period. But I didn’t see a despondency in that, there’s an acceptance of melancholia being a part of life, that’s why I don’t think it’s depressing.”

7. Pearl Jam – Black

“I know someday you’ll have a beautiful life / I know you’ll be a star / In somebody else’s sky”

Pearl Jam wrote this sad tale of lost love. Eddie Vedder wrote the lyrics while he traveled to Seattle. “I know someday you’ll have a beautiful life/ I know you’ll be a star in somebody else’s sky” are the lyrics fan love to sing along to.

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Eddie Vedder said of the meaning: “The song is about letting go. It’s very rare for a relationship to withstand the Earth’s gravitational pull and where it’s going to take people and how they’re going to grow. I’ve heard it said that you can’t really have a true love unless it was a love unrequited. It’s a harsh one because then your truest one is the one you can’t have forever.”

6. George Jones – He Stopped Loving Her Today

“They placed a wreath upon his door / And soon they’ll carry him away / He stopped loving her today”

Another really sad country song is Jones’ 1980 hit about a guy whose friend holds onto his lost love until the day he dies. His love for her never died, until the day that he died himself, which is the day he stopped loving her.

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This was Jones’ comeback song dealing with the law and his addiction. The song won Single of the Year at the CMA awards and took a Grammy for Best Male Country Vocal Performance.

5. Nirvana – ‘Something in the Way’

“Underneath the bridge / The tarp has sprung a leak / And the animals I’ve trapped / Have all become my pets / And I’m living off of grass / And the drippings from the ceiling / But it’s okay to eat fish / ‘Cause they don’t have any feelings”

Nirvana didn’t have just one sad song, they had many. But this one could be the saddest. It recounts Kurt Cobain’s period when he slept under a bridge in Aberdeen, Washington.

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Cobain recorded the track solo and acoustic and he sounds truly vulnerable.

Remember Harry Chapin? He’s #4 on the list.

4. Harry Chapin – Cat’s in the Cradle

“I’ve long since retired and my son’s moved away / I called him up just the other day / I said, I’d like to see you if you don’t mind / He said, I’d love to, dad, if I could find the time”

The epically sad hit single is about a father who is too busy to spend time with his son. And at the end of the song, the tables turn.

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The grown-up son is too busy for his elderly father. The song actually started out as a poem by Chapin’s wife, Sandy whose first husband’s father was a New York politician and they had a strained relationship. To make the song even sadder, Chapin died in a car accident in 1981 and he never got to see his own children grown up. You can grab the tissues now.

3. R.E.M. – Everybody Hurts

“If you’re on your own / In this life / The days and nights are long / When you think you’ve had too much of this life to hang on”

This is one of those songs that you put on the top of your break-up playlist. It’s just simply a tear-jerker.

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Most of this song was written by drummer Bill Berry. He said it was to be an anti-suicide song. Berry wanted people to know that they didn’t have to give up. He quit the band in 1997 and the whole band almost broke up but decided to continue as a trio. Berry then became a farmer.

2. Whitney Houston – I Will Always You

“So good-bye / Please don’t cry / We both know I’m not what you / You need
And I… / Will always love you”

The lyrics are sad because she will always him, yet she knows they aren’t good for each other and they need to go their separate ways. A lot of the time, people misinterpret it as a song about people who will be together forever. But it’s not.

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This song, as you probably know, was in the movie The Bodyguard, which Houston starred in with Kevin Costner.

Drumroll…the saddest song is…

1. Eric Clapton – Tears in Heaven

“Would you hold my hand, If I saw you in heaven? / Would you help me stand If I saw you in heaven? / I’ll find my way through night and day ‘Cause I know I just can’t stay here in heaven”.

Eric Clapton’s son Conor was four years old when he tragically fell to his death from the 53th floor of a New York building in 1991. Clapton and songwriter Will Jennings wrote this in memory of the child.

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By 2004, Clapton didn’t want to perform the song at his shows anymore and he dropped it.

So there you go – the saddest songs ever. We decided to make a playlist of all the listed songs for your easy access. Because we care. Enjoy!