

Watching through chronologically as you are will give Asteroid City the strongest punch. It’s one of my favs of his (and one of his funniest), but it’s so deeply in conversation with the rest of his body of work that it would be a lot harder to get on its wavelength without at least a few of them under your belt.
The Hustler is an excellent Paul Newman film about billiards.
Blow-Up is a bizarre anxiety drenched film about a photographer who may have captured evidence of a crime in the background of a photo.
Grand Prix is a neat film about formula 1 racing, with some of the best action photography ever.
If queer film is your jam, the work of Kenneth Anger is always worth checking out, Scorpio Rising being my favorite of those I’ve seen
If you like sci-fi and experimental shorts, Chris Marker’s La Jetee is pretty cool, and is what 12 Monkeys was based on.
As for super ambitious metanarrative experiments, Symbiopsychotaciplasm: Take One is incredible.