How Can You Mend a Broken Heart-Al Green
And So It Goes-Billy Joel
The Guitar Man-Bread
Trouble-Coldplay
Raining in Baltimore-Counting Crows
Just a Song Before I Go-Crosby Stills Nash & Young
Space Oddity-David Bowie
Come Undone-Duran Duran
Wasted Time-The Eagles
One is the Loneliest Number-Three Dog Night (the versions by Filter and Aimee Mann are great also)
Iris-Goo Goo Dolls
I Grieve-Peter Gabriel
I Know-Jude
Fat Boy-Jewel
Bye Bye Blackbird-Joe Croce(I don't know who originally did it)
Look at Me-John Lennon
Kent-there are several on Isola(the only album I've heard by them)that I think are sad
Going to California-Led Zeppelin(there is a line-I wondered how tomorrow could ever follow today-that I love)there are more but I'm sure you all know them
Perfect Day-Lou Reed
Blue in Green-Miles Davis
The Needle And The Damage Is Done-Neil Young
Fruit Tree-Nick Drake
River Man-Nick Drake
Black Books-Nils Lofgren
My Lover's Prayer-Otis Redding
Wish you were here-Pink Floyd
Comfortably Numb-Pink Floyd There are many more, They are one of my favorite bands
Roads-Portishead
Sail to the Moon-Radiohead
Ok Computer might just be my favorite Radiohead album and there are several on it that I think are sad(or feel that way to me)
Dream-Roy Orbison
Remember-Harry Nilsson
Pearls-Sade
Hey Jupiter-Tori Amos