Cristina - Things Fall Apart
We'll start off with somewhat of a bummer Xmas song, but one I absolutely adore. I got into Cristina (just Cristina, no Aguilera or Applegate) about eleven years ago via the "Mutant Disco" compilation that ZE Records put out. She immediately stood out to me as a very unique and witty 80s pop chanteuse who should've been bigger than Madonna if the world was fair. This song is about holiday angst, loneliness, and social misfits and the lyrics juxtapose nicely with the more upbeat instrumentation.
Run-D.M.C - Christmas in Hollis
Okay, this one is a little more popular. I loved Run-D.M.C. as a little kid, but somehow missed the boat on this one until I was in my teens, watching Beavis and Butthead when this video came on. Just a lot of fun from some legends of hip hop.
The Waitresses - Christmas Wrapping
Another good band who released on the ZE Records label. They're best known for "I Know What Boys Like", but this is also a solid classic. Nice and upbeat.
Takako Minekawa - X'mas Wish
She would go on to be a very unique and experimental synth-pop musician on her later albums, part of the Shibuya-kei scene of the '90s / early '00s, and later making music with Dustin Wong, but Takako Minekawa's first couple albums were pretty pop (and very fun in their own way). This track is off of an early EP, and even though it's not very demonstrative of her general sound, I always found it lovely.
The Pretenders - 2000 Miles
This one gives me the warm fuzzies when I hear it. I heard it when I was younger, but it most reminds me of Christmas 2012, living in LA, and had been jobless and feeling down. After four hard years of underemployment (thanks recession!) things perked up when JET Program called and offered me a job teaching English in Japan, which I accepted. This was the turnaround my life had been so needing and I heard this song a lot during that time, so I sort of associate it with a time of renewal.
Kurtis Blow - Christmas Rappin'
Another hip hop Christmas classic. I got into his music thanks to Grand Theft Auto Vice City, and heard this one not long after. Been a favorite since.
Ryuichi Sakamoto - Merry Christmas Mr Lawrence
I love Ryuichi Sakamoto (and YMO of course), and David Bowie, and was pleased to see the "Merry Christmas Mr Lawrence" starring both of them, thanks to my college roommate Yohei. Sakamoto composed a beautiful song with a melody that always sticks in my mind. He's a master at that sort of thing.
Well anyway, Happy Holidays to everyone. I'm sure as soon as I post this, I'll remember several more Xmas faves, but hey, here's a good start. Have a good new year!