Inspired by the folks at All Songs Considered, and culled from a playlist ("Pardon Me, Didn't I Break Your Heart") I created for Mistress Allison's exclusive Midnight Ramble series, V-Day edition, I present to you the most heartbreaking breakup songs ever (at least those with decent videos on YouTube).
Coming in on my "Top Nine of Oh-Nine" list:
And for the grand finale, Michael Caine's rendition of Roy Orbison's "It's Over" from the movie Litttle Voice. He could have just up and retired after this - it's that amazing.
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