It’s a decent film that I wouldn’t mind seeing again, and I feel comfortable suggesting it to others. I’ve had some not-so-pleasant recollections of this movie over time, and I'm certainly not claiming it's exceptional, but despite its shortcomings, it remains remarkably strong. The notion that Drew Barrymore (even back in 1999) could convincingly portray a high school student is absurd. I’m not generally a fan of hers, however she really shines in this part, even though it’s obvious she's playing a grown woman as a teenager. What the movie explores—and what she conveys beautifully—is the feeling of being caught up in the difficult experiences of high school when you don’t belong to the popular group. The casting was pretty good; David Arquette, Molly Shannon, J.C. Reilly, Leelee Sobieski, and Cress Williams (Black Lightning) all deliver solid supporting performances, as do Jessica Alba, Mary Shelton, and Jordan Ladd in their antagonist roles. The way the story is structured—a narrative within a narrative where one character retreats into another story—is strangely self-aware on several occasions, but it manages to be intricate without being overly dense, still humorous, and genuinely meaningful. Although I don’t foresee watching this frequently, I have to thank my mother: it's worthwhile, even two decades later.

Source on TMDB