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Elvis Presley — “Blue Christmas”
I think this is probably an unpopular opinion among people who know a lot more about Elvis than I do, but this has always been my favorite vocal performance of his: he sounds like he has the weight of the world on his shoulders, and the female backup singers somehow manage to make the whole thing sound even sadder.
The Partridge Family — “My Christmas Card to You”
I don't know, you guys. I was born in 1978 and this record has been in my family for as long as I can remember. It is unbelievably good from start to finish (save for the single most boring version of "Frosty the Snowman" you've ever heard in your life), but "My Christmas Card to You" is included here because it's the only original song on the record.
Marah — “New York is a Christmas Kind of Town”
No one really likes Marah, I don't think (or not anymore, anyway), but the Springsteen-loving Philly band released a predictably but also enjoyable rowdy Christmas album a few years back, and this is a definite standout, with lines like "Every subway stop is a Jingle Bell hop, every taxicab is a sleigh. Every icy wind is a long-lost friend to greet you on your way."
The Waitresses — “Christmas Wrapping”
The best thing about this song is how the narrator makes it clear right from the start that Christmas is actually her favorite holiday, so her continuing to insist that she's going to skip it this year is immediately sad rather than grouchy, which of course makes the happy ending even more satisfying. But maybe not as satisfying as those horns. Crazy.
They Might Be Giants — “Santa’s Beard”
Because what says Christmas more than a song about your wife cheating on you with Santa Claus? The line "I don't like that fat guy around" should not be quite as touching as it is here.