The Comedy Option: Clueless
While 1995 may serve as an exotic time-capsule now, Clueless is in an especially specific window in time. Travel back to time when Alicia Silverstone was a leading lady, Brittany Murphy was still with us, cell phones in schools were a hilarious novelty that could never become the norm, and Stacy Dash looked exactly the same as she does today. Also: super young Paul Rudd! Party with some Haitians and enjoy.
The Drama Option: Brick
Director Rian Johnson had a hot last year with Looper, but his first teaming with Joseph Gordon-Levitt was for this most unique take on the high-school drama. Blending teenage concerns with a classic noir tone and structure, Brick is exactly the change of pace you're looking for.
The Horror Option: The Faculty
A body-snatchers tale for the teen-horror craze of the late-'90s, the film sets up a rather smartly-cast collection of the hot teen stars at the time (Josh Hartnett, Elijah Wood, Clea DuVall) against an all-star team of alien-infested teachers (Robert Patrick, Piper Laurie, Jon Stewart, Bebe Neuwirth), all infused with the kind of verve you'd expect from Robert Rodriguez. An underrated gem from that era.
The Indie Option: Pi
Sure, this movie doesn't have anything to do with school, per se. But what else are you going to school for if not to be able to understand this mathematically and philosophically dense film? Darren Aronofsky's breakthrough was one of the foremost indie sensations of the '90s, and it's more than worth a look to see where such a prolfic director got started.
The Classic Option: The Paper Chase
I should note that there are classic high-school films like The Breakfast Club and Heathers also available for streaming, but I'm going to assume you've seen those a billion times, and if you haven't, you should. Or you could check out this 1973 film about the rigors of Harvard Law School. John Houseman won an Oscar for his portrayal as an impossible-to-please professor, and the film was later adapted into a TV series.
The Wild Card: High School Musical
We won't tell anybody if you won't.