You're talking about something a bit different, but I think movies from 1990 to 2010, give or take a few, generally have enough similarity in style, language, mannerisms, sense of humor, clothing, etc, to keep them "new" enough when seen the first time. There's something very 90s about Karate Kid and Point Break, which will clearly differentiate it from something a little newer in the 2000s, but it's a less steep difference compared to the 80s or the 2010s.

I think culture changed very minimally in those 20 years, and it's reflected in film. Even with drastic changes like the innovations in tech, the culture didn't change too much.

On the topic though, yeah, each generation will experience that effect relating to movies they saw in their youth.