My top five (I just went through programming three hours of Christmas music into my iPod, much to the chagrin of my girlfriend). But for me, the carols are more about the specific version (usually one I remember from my childhood), as opposed to the carol in general.
O Tannenbaum -- Vince Gueraldi version
Holly Jolly Christmas -- Burl Ives singing
Holly and the Ivy -- preferably instrumental version, George Winston has a nice version
Baby It's Cold Outside -- either the original by Bing & Doris Day, or the version from Elf, which is also excellent
What's This?--from the Nightmare Before Christmas. It really is fantastic and deserves to be played and performed far more than it currently is.
Runners up are the Chet Atkins version of Let it Snow and Chris Isaak's Blue Christmas.
It's not really a Christmas carol, but I also love the Nutcrucker Suite.
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