On an annual camp out with some friends the weekend before Tommy Dawkins' senior year he is attacked by a wolf. Little does he know that the wolf that attacked him is in reality a werewolf and that night is going to change his life forever.
Once every 70 years, a window of transference opens that offers Tommy a chance to pass his curse to another person. Merton volunteers, but that same day a bookmobile shows up in Pleasantville and people start disappearing.
When a character from a 1950s educational film gets sick of the rules he decides to leave the movie for Pleasantville. While in Pleasantville Butch decides to find someone to bring back with him and he decides Stacy is the perfect girl for him.
An exotic new foreign exchange student, Carole LeFevre, begins attending Pleasantville High. Tommy thinks that she has a certain Je ne sais quoi but he fails to realize quite how much they have in common. Stacey finds herself jealous of Carole and Tommy's chemistry.
A college sorority has their eyes on set on Stacy and Tommy could not be happier until she starts acting like a real "witch". Merton is convinced that they are sorority cyborgs but he's a bit off the mark.
Mertons old nemesis, Alistair Black, comes to Pleasantville, not only taking over Merton as president of the Gothic Fantasy Guild, but also casting a spell on Merton, rendering him invisible. Meanwhile, Tommy has to deal with a psychiatrist.
A florist sets Merton up on a date with her niece. However, the florist does not have a niece, and when Merton unknowingly goes out with the florist, she sucks the life out of him, turning him into an old man.
Tommy decides to donate blood, but he and Merton must retrieve it from the blood bank after learning that his werewolf curse can be transferred by blood, and contend with a group of vampires who raid blood banks.
Tommy breaks the high score on an arcade game that mysteriously freezes as he reaches the next level. This serves to release the games antagonist, Dirk Strykem, who has decided to destroy Tommy and Merton.