Xennials is a thing. People born between like 80-86 who are technically Millenials, but grew up with a lot of Gen X shit. That's me to a T (born in 85, graduated HS in 03). All my baby sitters (mostly older cousins) as a kid were Gen X and so I was exposed to all their shit. I watched Star Wars, Indiana Jones, and the Goonies on repeat. The first music that I felt belonged to me was Nirvana, Oasis, Sublime, and Beck. I have very clear memories of a time where there was no internet access for regular people (I don't think I had even heard of the internet until 4th grade), and cell phones were non-existent. But I am, on paper, a Millenial.
I was a freshman in HS when American Pie came out, and I definitely think it informs the way I remember that era more than Superbad (a movie I fucking love), which came out when I was graduating college.
I suspect this phenomena is more prevalent in people who grew up in small towns (as I did), as pre-internet it really did take literal years for cultural trends to catch up.
Varsity Blues and 10 Things I Hate About You were definitely major "high school" movies for me when I was in high school.