7. "Santa Baby" by Madonna (1990), recorded first by Eartha Kitt in 1953
The hyper-sexed Madonna is a caricature of herself here, sounding like a greasy spoon waitress shaking her tail feather for tips. Ditzing it up to get what you want is acceptable to a point (according to the Mad Men ethos). But even Betty Boop thinks this rendition is too cartoonish.
6. "The Chipmunk Song (Christmas Don't Be Late)" by The Chipmunks/David Seville (1958)
This song, along with "Grandma Got Run over By a Reindeer" and "All I Want for Christmas is My Two Front Teeth," should be confined to school pageants—and only school pageants in which real, live chipmunks demonstrate the ability to carry a tune. Alvin and the boys sing, "Want a plane that loops the loop/Me, I want a hula hoop/We can hardly stand the wait/Please Christmas, don't be late." Yes, Christmas, don't be late. Otherwise the Chipmunks might send Faith Hill out to find you.
5. "The Hanukkah Song" by Adam Sandler (1996)
Respect is due when a song comes along that is so funny, irreverent and outside the norm that it becomes a holiday staple. That said, the "Chanukah Song" contains cultural punch lines—O.J. Simpson, in particular—that seem more dated with each passing year. Few film comedies hold up to countless viewings, and Sandler's song isn't exactly the musical equivalent of Monty Python and the Holy Grail.