Even after having seen it many times, there’s nothing that makes me laugh like seeing Chaplin struggle on the high wire while being tormented by monkeys, or being chased by a mean donkey, or trying to learn how to be funny in “clown class”.
The OP took mine. The Philadelphia Story was just so funny and remains so for me even now. And Casablanca is an iconic movie, setting its own place in history.
My criteria amounts to what films I could pop in the machine and watch any time, and enjoy, no matter how many times I’d seen them before. And those would be “Dr. Strangelove” and “Casablanca.”
I recently watched ‘A Soldier in the Rain’, with Jackie Gleason at his funniest and a young Steve McQueen. It was great. I love the ‘Thinman’ movies, too.
A drama I like is ‘The Children’s Hour’.
I love all vintage movies. All that have been mentioned are good ones.
Lots of Billy Wilder films making it into people’s choices…Double Indemnity, Sunset Boulevard, Some Like It Hot, The Apartment. You guys definitely have excellent taste.