We've all been through heartache and pain, and music often helps us articulate our deepest emotions in ways that we can’t express in other ways. We connect with a melody and its lyrics to release and express our deepest sorrows and anguish. But which songs evoke an especially deep sadness? In this blog post, we’ll take a closer look at some of the most heartbreaking songs ever written—from classic hits from Johnny Cash’s “Hurt” to Adele's “Someone Like You”. 

1. You Are My Sunshine

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One user posted, “'You Are My Sunshine' often gets mislabeled as a children’s song, but if you read the full lyrics, you’ll realize how dark of a song it is. Also, ‘Bookends' by Simon & Garfunkel. It’s a personal choice, but it always gets me.”

Another added “Even just the chorus of you are my sunshine was enough to make me cry when I was a kid (and now). In the same vein as my darling clementine. Though one day I was messing around and singing ‘opposite' songs and. Well, ‘You Are My Moonshine' is a very different song.”

One user also commented, “Was hoping someone would say you are my sunshine. It's so sad.”

“God, my mum used to sing this to me as a kid and even now as an adult I cry buckets if I hear it…never knew why and mum even used to say to me ‘It's a happy song, why does it make you cry?' and now I know it's not just me!!!” one user exclaimed. 

2. Cat's in the Cradle

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One Redditor shared, “Cat's in the Cradle. Edit: I see this is bringing up lots of comments and emotions in some people. I would like to share this advice with those of you who had parents that weren't the greatest and this song hurts: Use it to motivate you to be better. If you have kids, be the parent you wish you had.” 

Another user added, “Trivia: This song is written and performed by Harry Chapin, however it seems many many people think that it was sung by Cat Stevens. Probably due to the word ‘Cat' and also because Cat Steven's released an album called “Cat's Cradle”. Cat Stevens NEVER performed this song. (Well I mean in public, maybe he played it at home for fun.)”

3. Fast car by Tracy Chapman

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One user shared, “Fast car by Tracy Chapman.”

Another replied, “Nothing gets the mundanity of how the poverty cycle destroys someone. Someone who had dreams but had life and the struggles slowly made them impossible. It's the hope that kills you.”

“My God, this one breaks my heart every time. All she wants is a chance to get away….and be someone,” a third user replied. 

4. Hurt

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Another user responded, “Johnny Cash’s cover of Hurt…” 

One user also commented, “94% of people have never heard the original. 5% believe he wrote it.”

Another exclaimed, “I still like Trent Reznors version better.”

A Redditor seconded, “As unpopular as that is… so do I.” 

One user added, “Thank you!!! I heard the Cash cover and was like…'meh'… I do not get why it’s so popular. I grew up listening to the live/concert version by Reznor and it’s SO MUCH better…” 

“I think a lot of it is because of when he sang it ‘toward the end', the history he had with drugs, and just knowing that his singing was full of emotion and understanding because of those experiences. But mostly because it was different…an old formerly insanely popular artist covering a much newer band's music,” one Redditor concluded. 

5. Tears in Heaven

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One user commented, “Tears in heaven, once you know the backstory, its hard to dispute.”

Another replied, “My mom was a huge Clapton fan. The day the news story came out about his son she cried. She'd change the channel when the song came on the radio. I have a hard time with it, too.”

A third user also shared, “Yeah. I can’t listen to that one either. The story behind it is just too tragic.” 

6. Nutshell – Alice In Chains

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One user posted, “Nutshell – Alice In Chains.”

Another added, “Alice in Chains can get you on the emotional side. I'll also say Black Gives Way to Blue is up there on the sadness scale. The cover version Chris Cornell's daughter does in tribute is heartbreaking.”

7. 4th of July

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A user posted, “4th of July—I for one always tear up while listening to this song, the beat mixed with the words just makes it incredibly sad but it’s also one of my favorite songs.”

Another user asked, “Sufjan Stevens? I think there's a bunch of songs with this title. Aimee Mann's song by the same name comes to mind, too—one of my favorites of hers. But yeah, Stevens is a brilliant tearjerker.”

The original poster responded, “Yes by Sufjan Stevens, I’m sorry it took me a while to get back to you. I’ll listen to the song by Aimee Mann, it sounds very interesting.”

8. Alone Again

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An online user shared, “Alone Again Naturally by Gilbert O’Sullivan—I know he said it’s not autobiographical but the verse where he sings about his father’s death and his mother’s reaction always struck me as desperately sad.” 

9. Floating in the Forth

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One user posted, “Floating in the Forth by Frightened Rabbit. RIP Scott.”

Another added, “So many of Scott’s songs make me cry.”

A third user responded, “He had a knack for it. Especially his Owl John stuff. A Good Reason to Grow Old is devastating, especially now.”

One user commented, “That is my choice as well. I can't listen to Frank Turner's song about Scott either.” 

10. He Stopped Loving Her Today

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One Redditor shared, “I can’t believe no one has mentioned this one yet: He stopped loving her today—George Jones.” 

Another added, “My stepdad never got over my mom. Through the years he would call her and try to get her back. Way after all my brothers and sisters were grown and had kids of their own, he still called. They were both married to other people, he still called. Yes their spouses knew. Everyone was friendly. It was a running joke. He would call to discuss something that was going on with one of the kids but just had to interject something about maybe coming to see him sometime. He was diagnosed with cancer and it progressed at lightning speed. In his final few days he was admitted to the hospital. He just kept hanging on.

“The consensus among the medical staff was that he was waiting on someone. With everyone’s blessing, my sister called my mom and asked her to come to the hospital. When she arrived he she leaned in and said, ‘Hello Harry.' He woke up and managed to sit up. My mom hugged him and told him that she had always loved him. She thanked him for giving her all these beautiful children. She kissed him on the lips and said goodbye. She walked out of the room in tears, of course. He died before she could get to the parking lot. They played that song at his funeral.”

One user empathized and replied, “That’s truly heartbreaking. I’m sorry for your loss.” 

Original Reddit thread here.

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