For laughs, winces and surprising emotional weight try The Office Christmas Special. It was described by Johann as “a beautiful, bittersweet, and downright painful final send-off to the UK version of The Office. To enjoy the Christmas special it’ll be fine if you haven’t watched the first two seasons (even though you must have been living under a rock). But everything about this powerful ending to the show plays with the investment an audience has made with each of the characters “whether out of sympathy or pity.”
For nostalgia, warmth and wry observations it would be hard to do better than A Christmas Story, which I described as a film that “charms because it pokes fun at children’s capability for silliness yet also respects their capacity for earnestness (e.g., It *is* a breach of etiquette to go straight to a triple dog dare without an intervening triple dare). Though sweetly nostalgic about childhood in some ways, the film does not overly romanticize it: A Peter and the Wolf-esque subplot features a fearsome bully named Scut Farkas.”
And for a darker yet ultimately uplifting Christmas story, there’s always Dickens’ masterpiece about Ebeneezer Scrooge. Two markedly different but top notch adaptations are described here.