Lonely Boy, Andrew Gold
Bill Withers - Grandma’s Hands; a quite enjoyable song nonetheless.
Bill Withers - Ain’t No Sunshine; is just great.
“Willing to Wait” by Sebadoh.
Biggie Smalls - Suicidal Thoughts; yes, rappers can be deep (plus you get to hear a pre-famous P. Diddy).
Tupac - Papa’z Song; you can’t have a Biggie song without giving a shout to Tupac.
Tracy Chapman - Fast Car; glimpses of intergenerational poverty and quick fixes.
Yeah, Cat’s Cradle for me too.
I Never Will Marry. I first heard Linda Ronstadt’s version, but I know there are others. Some personal significance, which I was beginning to realize at age 20.
This was one I came in to mention. I had never seen the video before today though and I’m glad I hadn’t. The song alone is so much better than with the cheesy video.
Tears in Heaven by Clapton was very sad when he played it during Unplugged. I think it was the first time he ever played it live from what I heard. Eric Clapton - Tears In Heaven - Unplugged - alternate take - YouTube
This live version of If You’re Readin This was very good by Tim McGraw. Very sad tune. Tim McGraw If You're Reading This - YouTube
Cat’s Cradle, for sure. Ye gods.
This song always makes me cry - Death Cab for Cutie Someday You Will be Loved.
Damn Aussies and Kiwis:
“White Wine in the Sun” Tim Minchin
“Better Be Home Soon” Neil Finn’s live ARIA performance, in tribute to the late Paul Hester
“Hurt,” no matter who sings it.
“Don’t let the sun go down on me” by Elton John makes me sad, though I am not sure why.
“Vibrate” by Rufus Wainwright—beautiful song about loneliness. Sad.
Neil Young’s (with Buffalo Springfield) ode to a lost love is the saddest love song I’ve heard.
*I tried so hard to stand
As I stumbled
and fell to the ground.
So hard to laugh as I fumbled
And reached for the love I found,
Knowin’ it was gone.
If I never lived without you,
Now you know I’d die.
If I never said I loved you,
Now you know I’d try,
Babe, now you know I’d try.
Babe, now you know I’d try,
Babe.
Forever Autumn - Justin Hayward
If I Could Change Your Mind - The Alan Parsons Project.
Tom Waits. Oh gods, Tom Waits. ‘Cold Cold Ground’, ‘Georgia Lee’… I can barely even listen to ‘Green Grass’. Each of those has at least one line that just punches you straight in the solar plexus.
Radiohead, ‘Exit Music’.
‘Hurt,’ the Johnny Cash version.
This one was saddest because it came from a movie that was supposed to be fun.
Toy Story 2: When Somebody Loved Me. Sarah McLachlan
Made more sad when one realizes that the toys in the movies are the symbols or the avatars of the parents.
There’s something about it that’s different from most sad love songs. It’s unquestionably over, and the guy is just…sad.
Game over, man:
“I will wait for you”, - Connie Francis, from Futurama
If this doesn’t make you blink back a tear or two there must be something wrong with your heart:
Maybe less sad, than harrowing - Lou Reed’s The Kids from the album Berlin ( possibly the least happy record ever made ).
Mine are all pop:
Traces (Dennis Yost)
Now You’re Gone (Boz Scaggs)
Keep Me From Blowing Away (Linda Ronstadt)
For No One (Beatles)
Caroline, No (Brian Wilson)