I'm a big fan of Kevin Williamson's 90's screenplays, even when his denouements are impossibly convoluted (the ending of "Scream 2"). The problem with his directorial debut is that he is so clearly held back by a PG-13 rating and the then-recent Columbine shooting that, simply put, the film has no bite. Turns out Williamson without the self-referential snark and a few dead bodies is no fun at all.
Shitty direction and another cringe-worthy, goody-goody performance by Katie Holmes (really hot sex scene though), saved solely by Helen Mirren as the deliciously cunty teacher/villain. She JUST makes the whole thing work as an watchable, nostalgic time waster.