13 Of The Saddest Songs Ever Recorded, And People’s Stories About How They Affected Them

Have you ever heard a song that’s so incredibly sad, that it actually made you cry? I mean, if you’re human, it’s probably safe to say you have…


Well, when Reddit user u/_sogapeu_ posed the simple question, “What’s the saddest song you have ever heard?” to the r/music community, they came back with some really heartfelt and, honestly, quite moving responses. Here are the top voted results:

Note: This post contains songs that have some graphic lyrics about death, drug use, and lynching.

1.“Real Death” by Mount Eerie

Harmony Gerber/WireImage

“That whole album, A Crow Looked at Me, it’s about life shortly after Phil Elverum’s (aka Mount Eerie) wife died. Heartbreaking shit.”


Listen to the song here:

2.“The Drugs Don’t Work” by the Verve

The Verve
Gie Knaeps/Getty Images

“Came on the radio while I was driving to my father’s funeral after he died from cancer…spoiled a good song for me. And then, driving home afterward, and ‘Everybody Hurts’ by REM came on…what are the chances eh…switched the radio off and drove home in silence…”

—Franky Fistalot

Listen to the song here:

3.“Strange Fruit” by Billie Holiday

Billie Holiday

“I don’t think there’s any song that is in this thread or could possibly be in this thread that is sadder and more devastating than ‘Strange Fruit.’ Once I saw an old recording of it being sung by Holiday while I was in a hotel while traveling, I told my friends waiting for me at the hotel bar that I was just gonna stay in and try and sleep.”


Listen to the song here:

4.“I’m So Glad Mom Can’t See Me Now” by Leon Rausch

A guitar

“I walked by an old man experiencing homelessness, playing that song once, like it seemed to be his own. I don’t remember the entire song, but it really got me when he sang, ‘I’m glad my mom can’ Don’t see me now.’”


Listen to the song here:

5.“Sam Stone” by John Prine

John Prine

“‘There’s a hole in daddy’s arm where all the money goes.’ That line hits hard.”


Listen to the song here:

6.“Time in a Bottle” by Jim Croce

Jim Croce
Abc Photo Archives / Disney General Entertainment Content via Getty Images

“Came looking for this song. Thinking about Jim and him leaving behind his little boy. I still like the song and appreciate it, but it makes me sad every time I hear it.”


Listen to the song here:

7.“Fast Car” by Tracy Chapman

Tracy Chapman
William Campbell/Getty Images

“I always liked the guitar part that repeats through the song, but I only recently really listened to the lyrics. Most people can’t escape their past.”


“I always liked the line, ‘I had a feeling that I belonged.’ Just makes me think this poor girl never once felt special or even included. Ah shit, I’m going to cry.”


Listen to the song here:

8th.“Fourth of July” by Sufjan Stevens

Sufjan Stevens

“The first time I listened to this song, I bawled. We had just found out my mom’s cancer had metastasized. Now, it’s been two months since her passing, and I’ve listened to it once in that time. It was too painful . That song hurts too much.”


Listen to the song here:

9.“Elephant” by Jason Isbell

Jason Isbell
Barry Crowbar/Getty Images

“He’s got such a unique and special way of making you understand the heartbreak of losing someone you love.”


“This is an excellent answer. He’s one of the best songwriters of our time.”


Listen to the song here:

10“Nutshell” by Alice in Chains

Alice in Chains
Tim Mosenfelder/Getty Images

“They have plenty of incredibly sad songs.”


“Came here to say this. Cannot bring myself to listen to this song without ugly crying. Held my brother’s hand and listened to this song as we said goodbye.”


Listen to the song here:

11.“Vincent” by Don McLean

Don McLean
Radio Times / Radio Times via Getty Images

“‘American Pie’ deservedly gets all the attention, but this song, a tribute to Vincent van Gogh, is just as good.”

Listen to the song here:

12.“Fire and Rain” by James Taylor

Michael Putland/Getty Images

“It’s a song about a friend that died by suicide and James fighting his addiction.”


“Here is a quote from Taylor that I found while reading up on this topic. I think it really hits the nail on the head in regards to addiction, at least in my personal experience: ‘One thing that addiction does is, it freezes you You don’t develop, you don’t learn the skills by trial and error of having experiences and learning from them and finding out what it is you want and how to go about getting it, by relating with other people. circuit all of that stuff and just go for the button that says this feels good over and over again.'”


Listen to the song here:

13.Finally, “Black” by Pearl Jam

Pearl Jam

“‘I know someday you’ll have a beautiful life, / I know you’ll be a star in somebody else’s sky, / but why…why…why can’t it be, oh, can’t it be mine.’ The way Eddie Vedder’s voice cracks when he’s singing ‘why’…ouch.”


“Man, what a song! I think the MTV Unplugged version is my favorite where he’s crying out, ‘We…we belong together!’ at the end. Gets me every time.”


Listen to the song here:

Note: Some responses have been edited for length and/or clarity.

What about you? What’s a sad song that always makes you cry? Tell us in the comments below, and IDK, maybe there’ll be a part two!

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