1. Judy Garland, ''Have Yourself a Merry Little Christmas'' (1944 soundtrack version)
If you think this is a cheerful song, you (a) have been listening to the wrong versions and (b) must have missed our article on the history of this perennial. (Get up to speed here.) The ballad was penned for a particularly sad scene in Meet Me in St. Louis where Judy Garland tries to convince her tearful little sister Margaret O'Brien that it's okay they're about to move away from their beloved home and friends. Of course, Garland does such a poor job of uplift here that the musical number ends with O'Brien running off and destroying a snowman. That's our kind of sacrilege!
Image Credit: Everett Collection
Bah, Humbug: The 100 Greatest Down-and-Out-on- Christmas Songs
Had enough of traditional holiday cheer? OK, Little Bummer Boy, here's our gift to you: A playlist of holiday jeer, featuring Prince's ''Another Lonely Christmas,'' William S. Burroughs' ''A Junkie's Christmas,'' and more cool lumps of audio coal
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