Great list, Matt.
Every year, I make a 2 discs of holiday music. One which is acceptable to play at my mom's party, and another I keep in the car. If anyone is interested in them, PM me and I can upload it and send you a link.
A great Christmas album from last year came from (another!) artist who left us too early. But if you all haven't heard the holiday album from Sharon Jones & The Dap-Kings, you're missing out on some Christmas soul.