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Bob Dylan - "Girl from the North Country"
Bob Dylan has written hundreds of sad songs that could satisfy this
hastily compiled list - he's a master at evoking any emotion but he's
especially ingenious at tugging at sorrowful heartstrings - still,
"North Country" remains at the top of my list of Dylan songs to
soundtrack my crying into pillows at night. It finds him seeing to the
well-being of his once true love as he hopes that she will simply
remember his name. I can relate, as none of my ex-girlfriends have ever
referred to me by name - but simply as, "Hey asshole."
See Also: "Boots of Spanish Leather" - They're pretty much the same song.
Otis Redding - "Tennessee Waltz"
Originally written as a country song by Pee Wee King and made popular
by Roy Acuff in 1950, Otis Redding claimed it as his own on his 1996
album "Dictionary of Soul" as he belted out its verses in that
anguished, beautifully flawed deep soul voice that soared out of
Memphis and to the top of the charts before it came crashing back down
in a passenger plane over Wisconsin. The song recalls a night of
dancing to the Tennessee Waltz before an old acquaintance came along to
steal his baby away. "I introduced him to my baby, while, while they
kept on playing. That friend stole my sweetheart away from me." Otis
bleeds the verses as if on the verge of tears, proving that
cockblockers have been a thorn in the side of good-intentioned
gentlemen for generations.
Radiohead - "Creep"
You remember just as well as I do when you were in the eighth grade you
would sing this song into your bathroom mirror and cry and cry. As
hilariously pathetic as it is to look back on this humiliating time in
your life, when you saw your best friend walk hand-in-hand to the bus
with the girl you thought was the love of your life, it was like the
holocaust thrown into the great plague. Well, if you're reading this,
congratulations; you got through it, and I believe you owe thanks to
Thom Yorke, his lazy eye and the girls (just about all of them) who
turned him down and inspired this masterpiece of gloom and rejection.