I never get tired of watching "A Christmas Story" (USA, 1983), starring Peter Billingsley, who incidentally has grown up to be surprisingly good-looking, as well as a successful producer.
For me, the appeal of the movie came from several levels: I enjoyed the humor in it, which never seems dated, though it's based in my parents' childhood days. I also enjoyed hearing my father talk about Jean Shepherd, the narrator of the movie, and about the wonderful radio stories he used to tell. But most importantly, it's just good story-telling, which is sadly lacking in many saccharine holiday specials.
"You'll shoot your eye out!"