In reality, I cover my ears when most Christmas songs are playing and people think that I'm the Grinch. But when good musicians make Christmas music then life is good. Here's what I think is wrong, and right, about Christmas music.
Too Much Santa - I don't mind Santa Claus. I know that many people think that it's evil to tell your kids about an altruistic saint who gives people presents, but I don't. (So far, exactly zero criminals have traced their evil ways to 'Santa Disillusionment.') But during the holidays I hear way too much Santa music on popular radio. While buying groceries I have to endure every single song about Santa, and sometimes different versions of the same song since there are only so many. The holiday season is bigger than Rudolph, but when you insist on removing religion and deeper meanings from the season you end up with nothing but playful children's songs on the radio. When those songs lack a bigger context then you have a pretty empty holiday.
The Worst of Pop Music - Studios don't put much effort into Christmas songs. Pop stars who have no career (or who's career is tanking) are sent into the studio to record cheesy versions of 'Frosty the Snowman' or 'Winter Wonderland.' The music is derivative. The singing is dull. The arrangements are not interesting. Nothing new is brought to the songs. Instead, they give us pop music's weakest attempt. Pop music is bad enough, but when these artists and their studios are not even trying to reach their normal state of mediocrity then we get some really bad music. I understand why non-Believers hate Christmas when I have to listen to this stuff. (I would put Mariah Carey's work in this category, but legions of women threaten to descend upon me with blunt weapons when I criticize 'All I Want for Christmas is You.')
Sufjan Stephens - Everyone's favorite indie star has made some of the best Christmas music that I've ever heard. According to rumor, he hated Christmas because of its commercialism, but found new meaning in the holiday and then began to love it like he was a child again. His Christmas work covers some traditional songs ('Joy to the World,' I Saw Three Ships,' etc.) with very good arrangements that are, in my mind, the new "definitive" versions of some of these songs. And the original songs he wrote for the album are great, too. It's very inspired music that comes from a man who truly loves the holiday. The album is called Songs for Christmas.
Yo-Yo Ma - The best Christmas music, as far as skill and composition is concerned, is most certainly found on Yo-Yo Ma: Songs for Joy and Peace. I don't own many albums with better musicians and better arrangements. This album brought together some of the finest musicians in the world (Yo-Yo Ma is the most famous cellist alive) and recorded them playing beautiful arrangements of traditional Christmas songs. I listen to it all year, because the music is just that good. The songs include old classics like 'Wexford Carol' and 'Wassail Song,' but it also has James Taylor doing 'Here Comes the Sun' and a musical arrangement of 'Happy Xmas (The War is Over).' I can't recommend a better album for the season. If I only got to have one Christmas album, it might be this one.
Vince Guaraldi - Guaraldi is the jazz genius behind the classic Merry Christmas Charlie Brown album. It's great. If you haven't heard it, try to find some recordings of 'Christmas is Coming' or 'What Child is This' and see if that doesn't put you in the holiday spirit. If you only remember the music as little kids singing boring songs, then you should really go back and check out the good stuff from Guaraldi's piano.
That's it. Of course, I could have mentioned certain individual recordings (Bing Crosby's recording of 'Do You Hear What I Hear' comes to mind), but I tried to stick with entire albums. What albums did I leave out?
Edit: Oops, I forgot one. In the comment section, Brian reminded me of Andrew Peterson's Behold the Lamb album. it's very good, and tells the biblical story of Jesus through many excellent songs. I saw the live performance and it was wonderful.