Now, I think anytime after Thanksgiving is fair game to break out the holiday tunes (and I don't mean to be Christmas exclusive, I'm a big fan of the Hanukkah Song by Adam Sandler as well).
There are the old classics, and I have always been a Bing Crosby fan, and can go for some Sinatra as well. But Bing singing White Christmas always puts me in the holiday spirit, I love that deep, rumbly voice. Ah, Bing, take me for a sleigh ride, I'm there. (ever seen Holiday Inn? With the exception of one notably un-PC scene, it's a gem). My dad plays these songs on the stereo while we open presents on Christmas morning.
But before that, when we decorate our tree, there are three classic albums we always put on the old record player to get in the spirit. First, my beloved Charlie Brown Christmas. The record is a recording of the entire special, every line and song. I have the whole thing memorized. "I have been extra good this year, so I have a long list of presents that I want. Please note the size and color of each item and send as many as possible. If it seems too difficult, make it easy on yourself, just send money. How about tens and twenties?" -Sally. 
So first we go through that whole record, and then move on to Sesame Street Christmas, complete with a Bert and Ernie version of The Gift of the Magi, Oscar's "I Hate Christmas," and "The Night Before Christmas on Sesame Street." I recommend this album to everyone, it's amazing. 
The third of the tree trimming trilogy is Disney Christmas. Ours is an older version, that features a very young Molly Ringwald singing "The First Noel" and of course the hilariously awesome Chip and Dale (and Donald) rendition of "Christmas Don't be Late." Every time I listen to this, and get to the part when Donald gets mad and quacks up, I lose it. Man, I love that duck sometimes. And then you have the more modern classics, things like "Rocking Around the Christmas Tree," and Bruce Springsteen's "Santa Claus is Coming to Town" (if you don't know this, you should, because it's just done in such a ridiculous manner. It's a blue collar Christmas). I also enjoy the ridiculousness of the faux aged rocker Billy Mack (from Love Actually) singing "Christmas is All Around."
Also, because it should become a holiday staple, the Peter Griffin Christmas Album. Listen and love, my friends. So turn on your radio or tune into Pandora or pull out the old Christmas albums, and let's start getting into the holiday spirit!
