Chemo limo by Regina Spektor is mine.

Beautiful song, but it can be too sad for me sometimes if I'm in a more empathetic mind frame

White Sparrows by Billy Talent always gets to me when I listen to it

They gave her one more day

To say the words I couldn't say

I'm crying in pain, crying in pain

And I'm not looking for answers

No, I'm not looking for answers

But dear God, why did you choose her?

White sparrows fell from heaven and carried her away

Black arrows cut the strings of my heart, I kneel and pray

There's the absolute classic: Halpelujah by Leonard Cohen which is just a beautiful song about the end of love

But my personal favorite is: I Will Follow You Into the Dark by Death Cab for Cutie, really the whole Plans album is amazing and wrecks me still.

Bright Eyes - When Winter Ends.
https://youtu.be/5-B7va1HaF0

Freaking amazing song.

Roads by Portishead.

Great song, but in my personal opinion, Smashing Pumpkins cover is better, even though I don't like them as a band.

Ahh shit. I read the rest of this thread, and an honorable mention is Tom Waits - Long Way Home.
https://youtu.be/hdyscH9TsnA

Gets me every time:

https://www.youtube.com/watch?v=ZzdF77CoLE0

I got some news on you from a friend
you’re in Charlotte again
teaching Spanish at high school

he said you’re going by Joy
you cut your hair like a boy
& you don’t talk to your old friends

I found a picture from before the fight
we’re in natural light
& you’re sitting on my lap
like everything’s alright

I’ve walked around with you on my mind
the names we used at the time
you know I’ve changed myself since then

I’ve thought on things that we said
what if we’d had the kid
I guess he’d be 15

I found a picture from before the fight
we’re in natural light
& you’re sitting on my lap
like everything’s alright

Thats cheating.

Blonde Redhead, "For the Damaged"

"Somewhere Out There " from American Tail

Oldie but Goldie & the saddest song I've ever heard: Gilbert O'Sullivan - Alone Again (Naturally)

The Living Years - Mike + The Mechanics

As I get older, it gets harder to listen to it.

Jolene as covered by Jack White. Dolly Parton singing it is also great, but to me it comes off as just another country song about infidelity. When Jack White covers it, it seems to take on a whole other perspective, but I guess that also depends on the listener too and what they project onto it.

Mad World - specifically the Gary Jules version. Even Tears For Fears like what he did with it.

Amanda Palmer's The Bed Song (YT link)

Lately I get got by Rise Against's People Live Here (YT link)

The National - About Today

Radiohead - Pyramid Song

Sufjan Stevens - Carrie & Lowell (album)

Adam's Song by Blink 182

Your heart is a muscle the size of your fist by Ramshackle Glory

Haunted by Deep Purple.
https://m.youtube.com/watch?v=bigkSWMEUQ0

“Hanging on in quiet desperation is the English way…”

“And I don't care what you're called
Tell me later, if at all
I can wait a long, long time
Before I hear another love song”

The different renditions tell slightly different stories IMO. There's also a very fine bardcore version by Hildegard von Blingin' that changes it to the story of a regretful immortal by only altering maybe 20% of the lines. I like all three versions for different reasons.

• Big Rude Jake -- The Diner
• Reverend Beat-Man -- Today Is A Beautiful Day
• The Dead Brothers -- Everything's Dead
• Steam Powered Giraffe - Honeybee
• The Violent Femmes -- Johnny
• Dwight Yokum -- I Sang Dixie
• Leonard Cohen -- Joan of Arc
• The Cranberries -- Zombie
• The Tragically Hip -- 38 Years Old
• Blue Rodeo -- Bad Timing
• Blue Rodeo - Hasn't Hit Me Yet

Goddamn it, OP, you've destroyed me. Thank you for listening to my mix tape.

"Last Kiss" the Pearl Jam version

And honorable mention to:

"The Last Remaining Light" by Audioslave

Marrow by 36 Crazyfists

Deference for Darkness - Halo 3 ODST Soundtrack

Emmylou Harris wrote two of my tearjerker songs. Both amazing and so sad.

Red Dirt Girl, and Boulder to Birmingham.

I Am The Antichrist To You by Kishi Bashi.
My first time listening to it was in the Rick and Morty Episode with Planetina. I loved it and looked it up afterwards. Love the video too, still gets me a little sad every time.

That is such a great cover.