Way OT - favorite sad songs??

Tears in Heaven by Eric Clapton. A really depressing song, but a really good one nonetheless. 

"Pictures of You" by The Cure - memories of middle school angst for me. 

"Last night I dreamt that somebody loved me" by The Smiths

"Eleanor Rigby" by The Beatles

"Tears in Heaven" by Eric Clapton - written for his son who died at age 4

"Cinderella" by Steven Curtis Chapman - it's the backstory which makes it particularly tearful. originally written for his two young daughters as a reminder to cherish the fleeting moments with them. A few months later, his son was pulling into the driveway when one of those girls, 5 year old Maria Sue, got excited, ran into its path, and was killed. Maybe it just gets to me as a father of two daughters...

Supermarket Flowers by Ed Sheeran

Once upon a time by Frank Sinatra

Just off the top of my head:

"All That's Gone" by Tom McRae.  If you like to wallow in the lost promise of your youth, this is your jam.

"Ashes Everywhere" by Joseph Arthur.  If you like to suffer over loved ones who've died (specifically by suicide), this is your jam.

"Words Fail" and "So Big/So Small" from Dear Evan Hansen.  Really need to be taken in the context of the whole show, which is absolutely heart-shattering.

"I Know It's Over" by The Smiths.  Classic wallowing to an almost pathetic degree.

"Out to Get You" by James.  Sleepy paranoia.

"Happy Birthday, Johnny" by St. Vincent.  Wayward friends lost.

"If You Miss Me" by Trip Shakespeare.  For falling asleep.

"It won't be like this for long" by Darius Rucker.  The Mrs. played this song for me after our daughter was born and to this day (9 years later) I still can't listen to it without crying like a fat kid being told there's no more ice cream.

Weyes Blood - "In the Beginning"

Richard Buckner - "Hindsight"

Haley Heynderickx - "The Bug Collector"

Eels - "Railroad Man"

Mercury Rev - "Holes"

Phosphorescent - "Song for Zula" or "C'est la Vie #2"

Stop and Stare - OneRepublic

Also Day N Nite by Kid Cudi, but that's a diff type of song depending on what you define as sad

I always remember the full length theme from Cheers being really depressing, same with M.A.S.H.

"Marie," Randy Newman

"Fiddler's Green," The Tragically Hip

"Don't Forget Me," Harry Nilsson 

"Ocean Breathes Salty," Modest Mouse

"Summer's Gone," Kinks

“Majesty” by Madrugada, especially the live version at Tralfamadore. 

“The Fire Thief” by Hem.

“Forest Fire” by Lloyd Cole and the Commotions.

“I’ll Fall With Your Knife” by Peter Murphy. 

“Hymn To Her” by The Pretenders. 

“Concrete Angel” the acoustic version by Christina Novelli. 

“Her Song” by Hungry Lucy. 

“Bleeder” by Emiliana Torrini. 

When September Ends by Green Day has become a new favorite for me

Landslide by Fleetwood Mac always gets me

Just about anything by Journey or Air Supply qualifies

Pretty much any songs from the Once album by Glen Hansard 

Weary Kind from the movie Crazy Heart is good.

Very specific but The Wreck of The Edmund Fitzgerald is pretty sad.  "Does anyone know where the love of God goes when the waves turn the minutes to hours"

Love this question.

I feel a little out place, with so many references to Pearl Jam and Ben Folds Five etc, but for my money the saddest songs:  

1. Billie Holiday  - Gloomy Sunday (This song will tear at your soul - Nobody sang sad songs like Billie and this is her saddest). 

2. Pink Floyd - I Wish You Were Here. 

Wake Up - Mad Season

Say Hello to Heaven - Temple of the Dog 

Whale and Wasp - Alice in Chains 

Scarborough Fair - Simon and Garfunkel

Could Have Lied - Red Hot Chili Peppers

Angie - The Rolling Stones  

"Why" by Rascal Flatts.  Obligatory trigger warning: it's about suicide, but it is a beautiful song.

I nominate Tom Waits here as well, if you prefer to take your pathos with a hearty dose of bathos. "A solider's things" (poignant, never directly dealing with the subject); "Tom Taubert's Blues," (song for the dumped, a fifth of Bushmills deep in Copenhagen); "Time" (that you love, sadness cloaked in ambiguity); "World Keeps Turning" (to all the girls I loved before); "Where the Train Goes Slow" (on redemption and the lure of the low road). 

One of my favorite artists, Jason Isbell, is the current king of sad songs.

Elephant

If We Were Vampires 

There are several others too.

Since you like Elliot Smith, I'd check this cover out:

"What Sarah said" by death cab for cutie makes me bawl, like snot bubbles and everything.

Also "oh my God" - jars of clay

Nutshell or Down in a Hole by Alice In Chains 

Depending on age...

Akon - Lonely

or 

Bobby Vinton - Mr. Lonely

Adagio for Strings by Samuel Barber

It's on the Platoon soundtrack.

"songs that she sang in the shower"

"elephant"

- jason isbell. i rode the album Southeastern hard while getting sober from alcohol/dealing with crippling depression

"I can't make you love me" by Bonnie Raitt

"Take it down" John Hiatt

Down in it

NIN

30 Seconds to Mars - Alibi

Epic slow buildup to last verses with Jared Leto just belting out "I fell apart"

Ohne Dich (Without You) - Rammstein 

194 comments filled with sad songs?

I don't think I could come up with even one, and I'm already dead.

BPONE rules, apparently.

Dude, DO NOT LISTEN TO SAD SONGS.

Sad songs are not gonna help one iota. Why dwell in misery and unhealthy idealism?

Rough patch?

Death metal is always best.

I recommend Slayer, Raining Blood.

Also check out Prong, Snap your fingers, Snap your neck,  and our teutonic friends Rammstein: https://youtu.be/1kB64dLWJ6s

Always a great pick me up!!