Best Breakup Songs of All Time

Sad songs say so much.

Videos by American Songwriter

Here’s our superior list of classic breakup songs:

1. Delia’s Gone – Johnny Cash
2. Ain’t That A Shame – Fats Domino
3. Cryin’ – Aerosmith
4. Torn – Natalie Imbruglia
5. Lost Cause – Beck
6. Free Bird – Lynyrd Skynyrd
7. You’ll Think Of Me – Keith Urban
8. What it Takes – Aerosmith
9. Gimme Back My Dog – Slobberbone
10. The Winner Takes All – ABBA
11. In The Wee Small Hours of the Morning – Frank Sinatra
12. Troy – Sinead O’Connor
13. Intentional Heartache – Dwight Yoakam
14. It Ain’t Me Babe – Bob Dylan
15. I Must Be High – Wilco
16. Overs – Simon and Garfunkel
17. Since I Been Loving You – Led Zeppelin
18. Give Back the Key To My Heart – Uncle Tupelo
19. The Way You Used to Smile – The Research
20. I Will Survive – Gloria Gaynor

Grand Prize Winner:
Sacrifice – Sinead O’Connor


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  1. Great list! However, I think “Troy” should be the grand prize winner. From the moment the song starts out, very quietly, and then building to a crescendo, the raw emotion is there all the way through.

    PS: Sounds like you have a cool mom and dad!!!

  2. for anybody interested, they should check where there is a fabulous oct O8 live version, with full kitchen sink orchestra, of ‘troy’. its was the first time in twenty years she had sung it and it is still spine tingling.

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