PoppaGator--John Denver recorded "Christmas is Coming, the Goose is Getting Fat" as a round with the Muppets. Miss Piggy gets a bit too much into her part. Still cracks me up.

The Cherry Tree Carol--great proto-feminist storyline
O Come, O Come, Emmanuel--sing it for Advent in plainsong mode
Lo, How a Rose (NOT the modernized version, which scans like a lump of bread dough kicked down a flight of stairs)--a quiet, beautiful song for a Christmas Eve service
The Hills are Bare at Bethlehem--explores the metaphor of hope born in winter with minimal schmaltz (Fun Fact: we celebrate Christmas in winter, but Jesus was born at lambing time; He died and rose around lambing time too, so we had to spread the feasts around the calendar a bit, and besides people need a midwinter feast in northern latitudes, witness Saturnalia and Yule.)
Away in a Manger--always chokes me up
The Holly and the Ivy--another proto-feminist traditional carol
Last song for Christmas eve: Silent Night, softly, with candles
First song for Christmas morning: Joy To the World, with all the stops pulled out!

Feminism aside, Joseph tends to get short shrift. He made a huge leap of faith, after all, and was good to Mary even when he thought she had slept around on him--he could have humiliated her publicly but chose not to. Anybody know any good carols about Joseph?