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Okkervil River — “Listening to Otis Redding at Home During Christmas”
A song about Christmas music doing exactly what Christmas music is supposed to do? Yes, please, especially with the perfectly placed Otis Redding homage snuck in there at the end.
Otis Redding — “White Christmas”
Ugh, ok, fine. I wasn't going to include it, but at this point there's no use hiding. Just go ahead and give yourself over to it completely. (You have more to drink, right?)
Wham — “Last Christmas”
It might feel like something of an amateur move, including this on your playlist, but don't worry: as long as you stick with the original and not one of the millions of terrible covers that have been pushed on us in recent years, there is no shame.
Brenda Lee — “Rocking Around the Christmas Tree”
If I had to cut this list down to 10 songs, "Rocking Around the Christmas Tree" would still be on it. The sax solo, the instrumental breaks, and of course Brenda Lee's vocals, recorded, almost unbelievably, when she was only 13 years old.
The Ramones — “Merry Christmas (I Don’t Want to Fight Tonight)”
In the video for this song, there's a couple fighting before the song starts, and the woman says, in the thickest New York accent, "We were supposed to visit my parents in Mineola!" This song would still be really awesome even if my high school wasn't in Mineola and my parents didn't live in the next town over, but it certainly helps.