Songs that Make You Sad Every Time you Hear Them

Hands down, Clapton's "Tears in Heaven." It didn't really affect me as a freshman in '91-'92 when it came out even though I knew it was about the death of his son. Once I had children of my own, it was a lot different.
 
These Little Things (Remind Me of You) - Ella Fitzgerald

It's Too Late - Carol King

Memories of You - Benny Goodman
 
While My Guitar Gently Weeps
I'll Be True To You
The Dance
anything from Townes
most anything from Ryan Adams
 
"Hallelujah" - Jeff Buckley
"Somewhere Over the Rainbow/What a Wonderful World" - Israel Kamakawiwo'ole
"Desperado" - Eagles
"Hurt" - Johnny Cash
 
wish you were here - pink floyd
tell lorrie i love her - keith whitley
 
Rex's Blues - Townes Van Zandt

A few months back I started a thread called "I am making a cd of heartbreaking songs." It may still be search-able. It had some great stuff.
 
Bonnie Raitt - "I can't make you love me."

Steven Curtis Chapman's song "Cinderella" is terribly sad to listen to with the tragic death of his youngest daughter.
 
Whenever I hear any SRV a little part of me is sad because his talent and genius will never be heard live again.
 
I'll further the above just a hair:

Amazing Grace on the bagpipes.

Life by the Drop
Good Riddance (Time of Your Life) - Green Day
 
"That's my job"---Conway Twitty
I cry like a ***** every time.

"There goes my life"--Kenny Chesney
makes me think about my daughters, and i do get misty.
 
The Gary Jules cover of "Mad World"
David Geddes "The Blind Man in the Bleachers" this is from '75, so most of you probably don't know it.
For some reason Bob Seger's "You're Still the Same" always puts me in a melancholy mood.
 

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