# What's the saddest song on your playlist?

**URL:** <https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858>\
**Category:** Cafe Society\
**Created:** [December 16, 2016, 3:47pm UTC](https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858 "2016-12-16T15:47:19Z")\
**Posts on this page:** 4\
**Page:** 4

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**Author:** ![ivylass](https://avatars.discourse-cdn.com/v4/letter/i/9de053/32.png) [@ivylass](https://boards.straightdope.com/u/ivylass)\
**Post date:** [December 19, 2016, 7:30pm UTC](https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858/61 "2016-12-19T19:30:37Z")

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I don’t have any particularly sad songs, but Ivylad [has one](https://www.youtube.com/watch?v=70Ikj1hZDnw) I refuse to listen to, just like when I flip the channels when the Humane Society ads come on.

Partial lyrics:

_Well I fly that plane called the Angel Flight  
Come on brother you’re with me tonight  
Between Heaven and earth you’re never alone  
On the Angel Flight  
Come on brother I’m taking you home_

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**Author:** ![NDP](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/ndp/32/55_2.png) [@NDP](https://boards.straightdope.com/u/NDP)\
**Post date:** [December 19, 2016, 8:11pm UTC](https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858/62 "2016-12-19T20:11:22Z")

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It’s a tie between these two:

[“To Love is to Bury”](https://www.youtube.com/watch?v=I4hKmQpcT1k) - Cowboy Junkies

[“How Can You Mend a Broken Heart”](https://www.youtube.com/watch?v=UgAFcvIw8J4)- Al Green version

They’re both great songs but not the best things to listen to if things aren’t going very well.

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**Author:** ![Finagle](https://avatars.discourse-cdn.com/v4/letter/f/b19c9b/32.png) [@Finagle](https://boards.straightdope.com/u/Finagle)\
**Post date:** [December 19, 2016, 8:24pm UTC](https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858/63 "2016-12-19T20:24:39Z")

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I listen to a lot of folk/acoustic singer/songwriter music which means my playlist is is just one continuous joyfest.

Bill Morrissey’s “Standing Eight” album was done after his divorce. So it’s got some rollicking songs on it. [These Cold Fingers](https://www.youtube.com/watch?v=vWEmslNBrUs) is guaranteed to put a smile on your face. Not.

Lucinda Williams: [Sweet Old World](https://www.youtube.com/watch?v=qWJCu3d6EX0) is a song to friend or relative who committed suicide.

Justin Hayward’s [Forever Autumn](https://www.youtube.com/watch?v=hsCdlX-5UjE) is pretty damned melancholy.

I usually bring up Leonard Cohen’s “Dress Rehearsal Rag” in this kind of thread, but that’s not so much sad as just damned depressing.

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**Author:** ![stillownedbysetters](https://avatars.discourse-cdn.com/v4/letter/s/41988e/32.png) [@stillownedbysetters](https://boards.straightdope.com/u/stillownedbysetters)\
**Post date:** [December 19, 2016, 8:57pm UTC](https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858/64 "2016-12-19T20:57:57Z")

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**Words** by Skylar Grey

She did a straight (as in not the hip hop mix/sample version that is better known) girl-and-her-piano version of this song that brings back the sometimes problematic relationship I had with my now-deceased mother.

Grey herself has said she wrote the lyrics about her deceased grandfather.

The chorus is haunting.

It’s so loud inside my head  
With words that I  
Should have said  
And as I drown in my regrets  
I can’t take back  
The words I never said

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