The 25 Most Exquisitely Sad Songs in the Whole World 25 - The River - Bruce Springsteen
24 - Nothing Compares 2 U - Sinead O'Connor
23 - No Surprises - Radiohead
22 - A Change is Gonna Come - Sam Cooke
21 - Space Oddity - David Bowie
20 - That's the Way I've Always Heard it Should Be - Carly Simon
19 - Lost Cause - Beck
18 - I've Gotta Get a Message to You - Bee Gees
17 - Back to Black - Amy Winehouse
16 - Shilo - Neil Diamond
15 - My Mom - Chocolate Genius
14 - Anyone Who Had a Heart - Dionna Warwick
13 - Naked as We Came - Iron & Wine
12 - In the Wee Small Hours of the Morning - Frank Sinatra
11 - Brick - Ben Folds Five
10 - In the Real World - Roy Orbison
9 - Concrete Angel - Martina McBride
8 - Dance With My Father - Luther Vandross
7 - Hallelujah - Jeff Buckley
6 - He Stopped Loving Her Today - George Jones
5 - I Know It's Over - The Smith
4 - Hurt - Johnny Cash
3 - Eleonar Rigby - The Beatles
2 - Gloomy Sunday - Billie Holiday
1 - Chicken Wire - Pernice Brothers