This is partially inspired by @UsedJavelin's thread about Seven Samurai.
I watched a lot of the Western "film canon" when I was younger, and lately I've just been craving some good "artistic" movie content. But I don't trust the :reddit-logo: crowd nor the letterboxd nerds for serious recommendations, so I turn the question to my comrades
Modern Times [USA, 1936]
Bicycle Thieves [Italy, 1948]
Court Jester [USA, 1955]
Spartacus [TERF-Island, 1960]
Dr. Strangelove [TERF-Island, 1963]
Batman [USA, 1966] (Perhaps not the best movie, but hilarious)
In the Name of the Italian People [Italy, 1971] (obscure, but good)
Monty Python and the Holy Grail [TERF-Island, 1975] (IMO the life of Brian hasn't aged that well otoh)
Blues Brothers [USA, 1980]
Wings of Desire [West Germany, 1987] (this one is kinda obscure, but a comrade recommended it to me and I loved it)
The 1989 Batman is worth watching. It's one of the OG Capeshit movies but it's a lot more fun that the super-serious modern Batman.
Tim Burton plays Batman as black humor. The movie is full of fun absurdity, self-seriousness to the point of humor, great visual design. It's very different from modern capeshit. The sequel is also very good.
Another OG capeshit movie to check out is Blade. Wesley Snipes is a stone cold badass as the half-vampire vampire hunter Blade. The success of Blade is largely responsible for the resurrection of the comic book movie genre.
The best part is that Prince - yes, Prince! - does the soundtrack. The good 80s Prince no less. There were several hits and good music videos off that one.