Artist: Lady Gaga feat. Space CowboyReleased: 2008
With "Christmas Tree" Lady Gaga brought forth a song that is less subtle than "Baby, It's Cold Outside" and more repetitive than "The Little Drummer Boy." The line "my Christmas tree's delicious" is a double entendre so lazy it might qualify as a single entendre. On the other hand she captures what the Christmas season is really all about: fucking.
Artist: New Kids on the BlockReleased: 1989
Technically this is "Xmas" song and not a Christmas song, but I think we can still put it on the list, especially when it opens with that great Sean Connery in the role of Santa Claus impression. If you're listening to the song, be prepared to hear the phrase "funky, funky xmas" a lot, but if it makes you feel better, The New Kids on the Block sound as tired of singing it as you are of hearing it.
Artist: Cyndi LauperReleased: 1998
"Bonga, bonga, bonga. Do the Christmas conga."
Artist: The Cheeky GirlsReleased: 2003
The Cheeky Girls are a heavily-accented Romanian-born British pop duo whose entire catalogue seems to be entirely about boys, girls, and/or being cheeky. Given that limited subject matter, it's incredible that they have released two different, terrible Christmas songs. "Have a Cheeky Christmas" is included on this list, even though it's arguably a better song than "Boys and Girls (Xmas Time Love)". The latter gets only a passing mention here because it has fuck-all to do with Christmas: a few Yuletide references followed by lots of extended shots of people in a swimming pool. Both look and sound like they were produced in 1989 and digitized from old tapes.
Artist: Sufjan StevensReleased: 2012
In 2012, in perhaps the greatest feat of self-indulgence ever witnessed by man, Sufjan Stevens released a 40-track collection of Christmas songs ending with this twelve-minute long tune. I have a pretty high tolerance for twee bullshit but I can't make it more than four minutes of this song without rolling my eyes. It sounds like something a doughy court minstrel would sing for medieval king moments before having his head cut off for the crime of "obnoxiousness."