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Eazy-E — “Merry Muthaphuckkin' Xmas”
You know, let me be honest here: I usually wind up skipping this song if it comes on when I'm by myself. There are some funny moments, of course, but it's way too long and, well, sort of not that Christmasy. Regardless, leave it on your playlist just in case. It goes over well at parties.
The Pogues — “Fairytale of New York”
If you don't know, now you know. But you already knew. I love you guys. Every single one of you.
John Prine — “Christmas in Prison”
I'm not sure what kind of person you'd have to be to hear the lines, "It's christmas in prison/There'll be music tonight/I'll probably get homesick/I love you. goodnight" and not be totally crushed. Though I do know I would not want to hang out with you.
Alvin and the Chipmunks — “The Chipmunk Song (Christmas Don’t Be Late)”
Get the kid a fucking hula-hoop for christ's sake, you know? (This is another album I've had in my possession since roughly the time I was born. Shit just cannot be fucked with.)
Otis Redding — “Merry Christmas Baby”
Honestly, I think I included this one because I'm really into the organ part, and because it's fairly lighthearted, at least compared to his version of "White Christmas," which I sometimes physically cannot bear to listen to. No one has ever wanted another person's days to be merry and Christmases to be white as badly as Otis Redding did. Holy shit.