Harold and Maude (1971)
This strikes me as a film that was kind of hipster-ish, four decades before hipsters were really a thing.
One of the weirdest things about getting through so many classic movies at this speed is the amount of stuff I recognise from when The Simpsons, Futurama, and Family Guy parodied it. Like there was a scene in this that Stewie did word for word, and I never got what it was referencing. It’s really odd getting parodies backwards.