10 Songs That Make You Sad - topic courtesy of Yano
1) Tears From Heaven - Eric Clapton (I stole this from Yano's own list, but seriously, this makes me cry).
2) Breakfast at Tiffany's - Deep Blue Something (this song reminds me of a specific a time in my life that just makes me sad).
3) (Don't Go Chasing) Waterfalls - TLC (see above reason for #2 - same time in my life)
4) Don't Drink the Water - Dave Matthews Band
5) Mrs. Otis Regrets - Ella Fitzgerald
6) Thy hand, Belinda/When I am Laid to Rest - Purcell (from Dido and Aeneas)
7) La mamma morta - Giordano (from Andrea Chenier) (this and the one above were both songs I sang as an opera major. I almost always cried when I sang then - they just wiped me out. The song La mamma morta I found when watching the movie Philadelphia - It's the one Tom Hanks' character is listening to when he's hooked up to the IV and walking around - I bawled watching the movie and I just knew I had to sing it.)
8) Everybody Hurts - REM
9) Cry Me a River - Harry Connick, Jr.
10) The Long and Winding Road - The Beatles