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What is the saddest song you've ever heard?

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I have a strange affinity for sad songs. What is the saddest song you've ever heard?

I'll  start... Elephant by Jason Isbell makes me teary-eyed every time. It's just so brilliantly beautiful, visceral, and sad. 


Honorable Mentions:

  • Jamie by Zach Bryan and Charles Wesley Godwin. 
  • Travelling Soldier by the Dixie Chicks
  • Above the Clouds of Pompei by Bears Den
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"Doubt Comes In" from the musical Hadestown left me sobbing in the theatre when I first saw it performed. I consider it to be the saddest song I have ever heard, because, while I listen to many heartwrenching songs, almost all of the others end with at least a hint of hope.

Honourable Mentions

"Road to Hell (Reprise)" from Hadestown

"Home" from Beetlejuice

"The World Was Wide Enough" from Hamilton

"Cosmic Love" by Florence + the Machine

"Lua" by Bright Eyes

"Breathe" by Kooman & Dimond

(I tried to balance out musical theatre with "normal" songs, so I ended up with a lot)

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Can't pick just one, so I'll link a few of my favourites! Also, this status update might interest you.


"this is me trying" by Taylor Swift




"I Dreamed a Dream" from Les Misérables (can never pick which version I like best though)


"Breathe" from In The Heights




"The Logical Song" by Supertramp (might be too upbeat to be a proper sad song, but idk it makes me sad and that's what matters)




"my tears ricochet" by Taylor Swift




"It's Quiet Uptown" from Hamilton



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Ooh this is something I find interesting. Here are mine.

The Sixth Station

Elgar Cello Concerto in E minor (Though this sounds more like anguish than sadness)

Mei is Missing

Mad World (The Gary Jules one especially)

I also think that there are  some good compilations of sadder music on YouTube. I've found a few nice things there.

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"Molly Ban" from The Chieftains

"The Willow Maid" from Erutan

"Moorlough Shore" from Celtic Woman

Most songs done by Ella Roberts

"Arwen's Vigil" from the Piano Guys

"Love and Honour" from Celtic Woman

"Mise Eire" from Celtic Woman (definitely gotta look up the translation and history for this one to get the full effect)

You might notice that I like Irish music... ;)

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Without repeating some great songs mentioned above. . . additions:

  • "Cat's in the Cradle" Harry Chapin (1974) | Ugly Kid Joe (1993) See Below
  • "Last Kiss" J Frank Wilson and the Cavaliers (1964)
  • "The Sacred Bird" - Miss Saigon
  • "Tonight is the Night I Fell Asleep at the Wheel" Barenaked Ladies (2000) - especially the ambiguous ending (see below)

AM Radio was full of tearjerker songs in the 1970s, but Harry Chapin's 1974 hit "Cat's in the Cradle" is the king of them all. As everyone who ever attended summer camp knows, it's about a father who is too busy to spend time with his son. At the end, the grown-up son is too busy for his elderly father. It began as a poem by Chapin's wife, Sandy; her first husband's father was a New York politician and they had a strained relationship. Chapin died in a car accident in 1981 and he never got to see his own children grown up, making the song somehow even sadder. 

This hits close to home, since my father also died before we got passed out "strained-too-busy" relationship.

* * * * *

Re: Tonight. . . BNL has said in interviews they purposely chose the phrase "You were the last thing on my mind" to the audience could decide if the "singer' meant "I last thought of you as I died" - or - "I was dying and you were the furthest thing from my mind." Also:


Ed Robertson says that this song refers to Ed's brother Doug. Doug died in 1993 after crashing his motorcycle, and this song is apparently based on Ed's curiosity about what his brother was thinking about during his last moments.



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(sorry if there are repetitions)

"Pretty Funny" from Dogfight

"We Raise Our Cups" from Hadestown

"Once There Were Dragons" from HTTYD

"Words Fail" Dear Evan Hansen

"Something I Could Never Be" Wrabel

"Achilles Come Down" I listen to the Annapantsu version

"Who I'd Be" Shrek

"I'll Be Here" Ordinary Days

"No Voice" Bare

"In Case You Don't Live Forever" Ben Platt

Ummm sorry that's a lot...in musical theatre, they say that when the emotion is too strong to speak, you sing, so...

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Mr. Tanner - Harry Chapin

Cat's in the Cradle - Harry Chapin

Eleanor Rigby - The Beetles

But by far the saddest is The Shortest Story (Harry Chapin again). Lyrics in the spoiler:

I am born today
The Sun burns a promise
In my eye
Mama strikes me
And I draw a breath and cry
Above me a cloud
Slowly tumbles through the sky
I am glad, to be alive
It is my seventh day
I taste the hunger
And I cry
My Brother and sister
Cling to Mama's side
She squeezes her breast
But it has nothing to provide
Someone weeps, I fall asleep
It is twenty days today
Mama does not hold me
I open my mouth
But I am to weak to cry
Above me a bird slowly crawls across the sky
Why is there nothing
Now to do but die?

Yep, that's the whole song.

Edited by NerdyAarakocra
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