I divided mine up because there are so many ways you can categorize a classic
In terms of the critical darlings, the ones that the film school types will dissect in the future, I think you have a decent number. These are ones I *think* will fit into this area, mostly taken from Oscar nominees, definitely not exhaustive. Definitely the hardest to tell, because best picture winners, or even nominees, can be a product of the times and doesn't always mean lasting impact, even in the critical circles.
- Traffic
- Gangs of New York
- Million Dollar Baby
- Brokeback Mountain
- No Country for Old Men
- There Will Be Blood
- Lincoln
- 12 Years a Slave
- Whiplash
- Darkest Hour
- Dunkirk
- Jojo Rabbit
Then there are the crowd favorites, the blockbusters, comedies, animated, genre ones that are too often ignored by the Oscars. These are the ones you dust off the DVD for (or pull out of streaming) every so often just to reexperience.
- Spider-man 2
- Several of the Marvel movies, including Infinity War/Endgame, but also Iron Man, Thor: Ragnorak, Guardians of the Galaxy, maybe a few more
- Pirates of the Caribbean
- Dark Knight
- The Incredibles (and probably a few other Pixar films, they had a massive hotstreak in the early 2000s)
- Tropic Thunder
- 40 Year Old Virgin
- Knocked Up
And then, some I feel really fit into both categories:
- Gladiator
- LotR
- Inglorious Basterds
- Django Unchained
- Crouching Tiger, Hidden Dragon
- Avatar
- Dune
- Once Upon a Time in Hollywood
- Fury Road
- Wolf of Wall Street
- Everything Everywhere All At Once
This list certainly isn't exhaustive, but I definitely feel like there are a lot more than people may think offhand. Maybe it's just easier for things to get lost in the constant deluge of streaming options we have now, as opposed to having to depend on your trusty VHS/DVD collection.