Good watch, could watch again, and can recommend.
Look, I have some fairly negative memories of this movie over the years, and I'm not saying it is the best, but for all its flaws, it holds up surprisingly well.
The idea of Drew Barrymore (even in 1999) being able to pass for a high school student is nonsense. I'm not that big a fan of hers, but she nails this role even if she's clearly an adult at high school, but what the movie is about, and what she expresses wonderfully is the emotion of being in the traumatic experience of high school when you're not part of the ruling class.
I feel like they casted well enough: David Arquette, Molly Shannon, J.C. Reilly, Leelee Sobieski, and Cress Williams (Black Lightning) all do great support roles, and Jessica Alba, Mary Shelton, Jordan Ladd, and all do great antagonist roles.
The writing of writing about a story, in a story of one character hiding herself in another story is oddly meta on a few levels, but it remains complex without being overly complicated, is still funny, and has plenty of substance.
While I don't imagine I'm going to watch this very often, I'll have to credit my mother: this is worth the watch, even after 20 years.