Sure I enjoy the Christmas classics like "Walking in a Winter Wonderland" and "Let it Snow" but I wouldn't even count those as my favorite holiday songs.
I even really enjoy Mariah Carey's "All I Want For Christmas". It's kind of funny to think that "new" or "original" holiday music just doesn't come out anymore and be successful. Of course many artists do cover albums or re-makes but when is the last time you've really heard something original that's stayed popular? I'd count N'Sync's "Merry Christmas, Happy Holidays" but I'm not sure everyone would agree with me.
Along the same lines of "original" music, the songs I really like at Christmas are the terrible, cheesy holiday songs that kind make your ears hurt. Like "Dominic the Donkey" and "Grandma Got Runover by a Reindeer" (although that is super red-neck) but I think the best holiday cheesy music is classic Adam Sandler.
Seems fitting with today being the first day of Chanukah, I mainly love the celebrity call-outs but it's funny, catchy, and sure to be around for years.