1. "Keep Me In Your Heart" by Warren Zevon
2. "Tears in Heaven" by Eric Clapton
3. "Nothing Compares 2 U" by Sinéad O'Conner
4. "Hallelujah" by Jeff Buckley
5. "Casimir Pulaski Day" by Sufjan Stevens
6. "I Can't Make You Love Me" by Bonnie Raitt
7. "Hurt" by Johnny Cash
8. "Brick" by Ben Folds Five
9. "The Boxer" by Simon and Garfunkel
10. "The Freshmen" - The Verve Pipe
Obviously this is just the tip of the iceberg as far as sad songs go, and there are many great sad songs that didn't make the list. Please add your own personal favorite sad songs in the comment section below.