It's the first day of 7th grade at Curtis Junior High for Max Keeble (ALEX D. LINZ) and his best friends, Megan (ZENA GREY) and Robe (JOSH PECK). Having survived the summer of being pursued by the vindictive Evil Ice Cream Man (JAMIE KENNEDY), Max is hoping for a fresh start, particularly upon spotting the girl of his dreams, Jenna (BROOKE ANNE SMITH), who he knows from his paper route.
Yet, he discovers that middle school life isn't going to be much different than before. For starters, the school's two bullies -- Troy McGinty (NOEL FISHER), who's announced he's going to beat up one kid each day, and Dobbs (ORLANDO BROWN), who takes money from kids in the guise of investing it for them - have already picked on him.
To make matters worse, the fanatical school principal, Mr. Jindraike (LARRY MILLER) - who's after the job of Superintendent Knebworth (CLIFTON DAVIS) - reprimanded him for being thrown into a trash dumpster. Thus, when Max's parents, Lily (NORA DUNN) and Don (ROBERT CARRADINE), announce that they must move to Chicago by the end of the week for his dad's job, one would think that would be the last straw for Max.
Instead, the resourceful youngster decides that if he's moving and thus won't face the repercussions of his actions, he'll get even with those who've wronged him in the past. From that point on, and with the aide of Robe and Megan, Max begins his course of retribution, only to discover that not all plans are foolproof.