I hit the jackpot today.
First up: Herb Alpert and the Tijuana Brass, "Sleigh Ride." (Argh... it's not on YouTube. Well, "Spanish Flea" is as good, just not Christmas-y)
This fast-paced brass version of "Sleigh Ride" was always played at the K-Mart in my hometown during the Christmas season. It brings me way back to when that store had a full-service cafeteria / dining room in the back - as a kid it was such a big deal to get to eat there. I remember hearing the song over the store intercom when my sister and I went to K-Mart on our own to buy presents... if we're ever together, and those trumpets start playing over the radio or wherever, we both crack up.
Then, John Denver and the Muppets, "12 Days of Christmas."
A classic, in my book. The YouTube version linked to above is a bit different than the version I have on CD (yes, that's right, I have it on CD); the CD version includes Beaker and Dr. Bunsen Honeydew singing a verse, which is the best part.
When I was in college, there was a period of time when my sister, one of my older brothers and I all were in Madison at the same time. One December night we all piled in someone's car to go see the big drive-through holiday lighting display in a city park. We had a Christmas-music station playing on the radio, and this song got stuck in the rotation. I think it played three times in a row, in its entirety. Awesome.