The Shop around the Corner (1940)
I list this among my top holiday movies, but you’ll enjoy it any time of year. James Stewart and Margaret Sullavan delightfully embody employees at a Budapest gift shop circa 1940; they can barely tolerate each other but have unknowingly carried on a romantic pen pal correspondence. Supporting actors also do memorable work. This charming comedy has sweetness, wit, warmth, a bit of sassiness, and extremely likeable characters. I adore this film.
Other versions include In the Good Old Summertime (1949) and You’ve Got Mail (1998). Also check out Slate’s comparison of The Shop around the Corner to Stewart’s other Christmas classic, It’s a Wonderful Life.