1. "We Three Kings" (1857)
    Three magi from the east travel to Jerusalem bearing gifts and guided by a...mysterious light in the sky. Just google "wise men UFO" for plenty of weird and fun reading on the subject.
  2. "It Came Upon A Midnight Clear" (1849)
    A better depiction of the overpowering celestial music played by the angels announcing the birth of Christ than say, "Hark the Herald Angels Sing," which always struck me as humorous because of my mishearing "Herald" for "Harold" as a child. My favorite version is the one my grandma sings from her pew, a little sharp, reedy, and with conviction.
  3. "Grandma Got Run Over By A Reindeer" (1979)
    Speaking of grandma. A demented song in both content and melody, this one tells the story of a confused old woman, drunk and wandering, who's accidentally murdered by an indifferent magician in the sky, leaving her family to spend Christmas in mourning, save for the widower, who apparently is all ¯\_(ツ)_/¯
  4. "The Friendly Beasts" (English lyrics circa the 1920s)
    Talking animals.
  5. "Solar System Simon, Santa's Supersonic Sun" (1968)
    Francis Smith's hillbilly rave up about Santa Claus' son, who'll take up the mantle of Saint Nick once he expires. Only his duty is not merely earthbound: he visits all the inhabited planets in the galaxy, in just one day. Recently revealed to me by Christmas weirdo Andy Cirzan on the great Sound Opinions podcast. Visit www.soundopinions.org/Christmas to hear his excellent mixtape, "The Holiday Hangout at Hillbilly Holler."
  6. "Cherry Tree Carol" (early 15th century)
    In which the baby Jesus shuts up a grumbling Joseph by exerting command over nature from within Mary's womb. Spooky and beautiful. My favorite recording is by the Seeger Sisters on 1957's American Folk Songs For Christmas; Mark Lanegan does a haunting and worthwhile version, too.