The first Thin Man film takes place at Christmas time, and some years I'll watch that on Christmas Eve, and then the second film on New Year's Eve. The way the second movie picks up where the first one left off makes for a nice sort of connected experience.
I think you'll enjoy Preston Sturges' films, if you don't already know them. He had an incredible run between 1940 and 1948 during which time he wrote and directed 10 films, 8 of which are among the greatest comedies ever made. The Great Moment and Unfaithfully Yours are not quite up to par with the rest, but you can't go wrong with any of his films. I'd especially recommend The Lady Eve, Hail the Conquering Hero, and Christmas in July, but honestly, they're all amazing.
Other films you may like:
His Girl Friday
My Man Godfrey
It Happened One Night
The Philadelphia Story
Easy Living
Midnight
Bringing Up Baby
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