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The 20 Most Heartbreaking Songs Of All Time!


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A lot of too cool for the room no one knows picks. If we're including lesser known songs, how can this list not have any Jackson Browne - "Late for the Sky", "Sky Blue and Black"? And where is "All By Myself"?

Note this sentence though...

5 The Righteous Brothers: "You've Lost That Lovin' Feelin'," single (Philles, 1964) "You never close your eyes anymore when I kiss your lips": it's got to be the second greatest opening line of any breakup song ever. (The greatest is surely from Raspberries’ ballad "Starting Over": "I used to be so f***ing optimistic til you said goodbye".)

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How about a song that isn't about love torn asunder, but instead is about opprotunities missed. In some ways pondering what could have been is more painful then reflecting on the what you have lost. Harry Chapin's, "Cat's in the Cradle" has got to be in the Top 20. No happy ending on this one. In the right mood, it tears me up. Spend time with your kids, people.

Another vote for the first line in "Starting Over." You gotta love it...or hate it, depending on which side of the glass half empty/half full argument you are on.


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