Oliver Cross, who's used to being the most popular student at Stansfield Academy, has to deal with a new roomate, transfer student Chris Hilton, who instantly becomes a favorite of all the guys who always looked up to Oliver. Oliver starts to resent Chris suddenly being the object of everyone's attention. Meanwhile, Stansfield goes coed, with one of the new female students being Dinah McGee, grand-daughter of the headmaster.
Cross loses his deejay job at Radio Stansfield for threatening to go on air with a negative story about Coach Stokes' past that Mr. Rogers believes is false.
Chris looks forward to a visit from his parents, who are in South Africa filming a documentary. X, anxious about pleasing his father (El Jefe), asks Chris and Cross to help him become a star student in exchange for X helping them to clean their room, otherwise known as ""the Jungle.""
Chris and Cross are moved from ""the Jungle"" after being blamed for a recent rash of pranks at Stansfield Academy. They go on a mission to find the real ""Creeper"" and clear their name.
Cross is asked by Mr. Rogers to show Neena, a girl interested in attending Stansfield, around the school for a few days. He soon faces competiton from Chris as they go to extremes vying for the girl's affection.
Cross takes it to heart when Dinah tells him off after falling for another one of his scams. In an effort to show her he's not such a bad guy, Cross invites Dinah's boyfriend to Stansfield's Saturday night dance, not knowing the two had broken up and Dinah didn't want to see him.
Writing an essay on revolutions becomes an adventure for the students when the teacher offers tickets to a U2 concert to the student with the highest graded paper.
Mr. Rogers is quarantined with Mookie in ""the jungle"" after contracting chicken pox from Mookie. Chris and Dinah attempt to use the time to retrieve a damaged bust that's trapped in Rogers' office with a guard dog.
Punished after another prank, Chris and Cross have the run of Stansfield Academy to themselves while the rest of the students are on an overnight field trip, but they run into more trouble when they're joined by a couple of bikers and their girlfriends.
While trying to get Mr. Rogers to upgrade Stansfield's telephone system, Chris and Cross discover that X has been kidnapped and devise a plan to rescue him.
Cross forms a band in hopes of winning a talent contest after substitute teacher Andrew Randle inspires him to follow his passion.
The guys encourage Chris to run for student body president against a candidate Dinah supports. As they promote their candidates, Dinah and Cross discover a new level of their relationship with each other.