The 20 Most Heartbreaking Songs Of All Time!

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20. The Everly Brothers: "So Sad (To Watch Good Love Go Bad)",from It's Everly Time (Warner Brothers, 1960)
19 The Band: "It Makes No Difference," from Northern Lights - Southern Cross (Capitol, 1975)
18 Randy Crawford: "One Day I'll Fly Away," single (Warner Brothers, 1980)
17 Soft Cell: "Say Hello, Wave Goodbye," single (Some Bizzare, 1982)
16 Billie Holiday: "Don't Worry 'Bout Me," from Lady In Autumn (Verve, 1959)
15 Love: "Alone Again Or," from Forever Changes (Elektra, 1967)
14 The Pretenders: "I Go To Sleep," from Pretenders II (WEA, 1981)
13 Dusty Springfield: "I Just Don't Know What To Do With Myself," single (Phonogram, 1964)
12 Little Feat: "Long Distance Love," from The Last Record Album (Warner Brothers, 1975)
11 Smokey Robinson & the Miracles: "The Tracks Of My Tears," from Going To A Go-Go (Motown, 1965)
10 Bonnie Raitt: "I Can't Make You Love Me," from The Luck Of The Draw (Capitol, 1991)
9 Lorraine Ellison: "Stay With Me," single (Warner Brothers, 1966)
8 Abba: "Knowing Me, Knowing You," single (Epic, 1977)
7 Otis Redding: "I've Been Loving You Too Long," single (Volt, 1965)
6 Sinead O'Connor: "Nothing Compares 2 U," single (Chrysalis, 1990)
5 The Righteous Brothers: "You've Lost That Lovin' Feelin'," single (Philles, 1964)
4 Kate and Anna McGarrigle: "Heart Like A Wheel," from Kate and Anna McGarrigle (Warner Brothers, 1975)
3 Frank Sinatra: "I'm A Fool To Want You," from Where Are You? (Capitol, 1957
2 Roy Orbison: "It's Over," single (Monument, 1964)
1 George Jones:"He Stopped Loving Her Today," single (Epic, 1981)
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