Rudolph The Red-Nosed Reindeer: A Christmas classic, sure Elf and Home Alone are super funny and popular, but Rudolph is a real keeper.
Home Alone 2: Lost in New York: While I really like the first one, this one never gets old, and has a much more difficult situation for kevin. It's sad that they couldn't make another.
The Nightmare Before Christmas: I just love the movies that Tim Burton directs along with Edward Scissorhands, Frankinweenie, and Corpse Bride.
How the Grinch Stole Christmas: Beautiful animation, narration and music. Still holds up decades later. Something children.