We have a radio station in the Bay Area (96.5 KOIT) that plays holiday songs earlier and earlier each year. They used to play Christmas songs only on Thanksgiving Day and Christmas Day. Then one year, starting from Thanksgiving Eve all day the way through December 25, it was Christmas songs 24/7. Last year they started on the weekend before Thanksgiving. I actually tune in whenever I'm in my car or in the office.
My favorites:
Nat King Cole: The Christmas Song
The Ray Conniff Singers: Twelve Days of Christmas, What Child Is This
Bing Crosby: White Christmas
The Drifters: White Christmas
Dean Martin: Winter Wonderland
Percy Faith & His Orchestra: We Need a Little Christmas
Elvis Presley: Blue Christmas
Brenda Lee: Rockin' Around the Christmas Tree
Elmo & Patty: Grandma Got Run Over By a Reindeer
Perry Como: Home for the Holidays
The Eagles: Please Come Home for Christmas
Jose Feliciano: Feliz Navidad
Boston Pops Orchestra: Sleigh Ride
Burl Ives: A Holly Jolly Christmas
Bobby Helms: Jingle Bell Rock
Andy Williams: It's the Most Wonderful Time of the Year
Josh Groban: Oh, Holy Night
Celine Dion: Oh, Holy Night
John Williams (Home Alone Theme): Somewhere in My Memory
I dislike the some of the more modern/contemporary holidays songs, especially R&B renditions or anything by Mariah Carey.