I hate most Christmas music, but I had to make a playlist for a holiday party at work this year and I bought some pretty good stuff off of iTunes, including Jimi Hendrix doing the Little Drummer Boy and the McKenzie Brothers' Twelve Days of Christmas (which I didn't play at the party). That War is Over jam is pretty good, I think. Woody Guthrie does a good Hanukkah song. There's also some song that gets a lot of download action and remixing called Ocho Kandelikas that's a chahannukkkkkkkah song in spanish. There's Beck's Hanukay rap song The Little Drum Machine Boy and that's kinda cool if you wanna pretend it's still 1994, which I like to do sometimes. There's also this reggae song called "Irie Christmas" which I like. Eek-A-Mouse doing a musical version of "The Night Before Christmas" leaves something to be desired, but I bought it anyway.
Non-professionals singing Christmas Carols live is almost always sound punishment.