I'm a sucker for comedies from the 1930s and I should probably admit that some of my friends don't quite get that but... with that warning... here's a little about one of my favorites.
Holiday is a quirky slightly-romantic comedy with a serious side. It strikes the Chesternerds in our family as being rather Chestertonian as it's filled with fun paradoxes and looking at things up-side-down.
Johnny Case is a hard working man who meets Julia, the apparent girl of his dreams, at a ski resort. Back in New York City, he looks up the address Julia wrote on the back of envelope for him. Arriving at a palatial estate, he concludes that his girlfriend works at this house, and knocks at the back door, where he is let in by the embarrassed butler, who is without his jacket and was expecting a visitor at the front door, thank you very much. We of course discover that Julia is a wealthy heiress from a family filled with and interested in "important people".
I won't tell you the conclusion, but it's a fun story that shows the wrong-headedness of the snooty rich (particularly by showing how a member of the family who is perfectly normal and level-headed is, in this context, the black sheep of the family). Though the story is at times a little complex (and it touches upon some sad issues - particularly a brother who is trapped by family fortune and expectations and finds way too much solace in alcohol), my children really enjoyed the truthiness of the story and the many laugh-out-moments.
(photo from IMDB)