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Songs about holidays?
We sang the hymn "Come, Ye Thankful People" on Thanksgiving, so that has been in my head. I heard Bing Crosby and David Bowie's "Little Drummer Boy" on the radio for the first time this holiday season, and the part David Bowie sings is in my head too.
http://www.youtube.com/watch?v=sQyuTCvhA4U
Straight No Chaser - Twelve Days of Christmas (watch past the first 15 seconds- it's not what you think!)
Bruce Springsteen's live version of "Santa Claus is Coming to Town". I love when he says, "Are you being good? That's not many...you're in trouble out there!":D
Trans Siberian Orchestra "Christmas Canon" is just hauntingly beautiful.
Christmas Rap, The Waitresses.
It's not Christmas without that song.