My favorites that I watch each year, in order:
Movies
1. Home Alone
2. Christmas Vacation
3. Home Alone 2
4. A Christmas Story
5. The Santa Clause
Shows:
1. A Garfield Christmas
2. Mickey's Christmas Carol
3. A Charlie Brown Christmas
Other honorable mentions: How the Grinch Stole Christmas, Polar Express and Frosty the Snowman.