The big sports game is coming up and pranks against each team starts. Will steals the other teams statue and they retaliate by stealing Carlton, the team good luck charm. Phillip has the home alarm system upgraded and it causes problems.
Will goes with Phillip and Carlton to buy a new car. When Carlton wants Phillip to buy a car that Will thinks is dull, Will convinces Phillip to get a convertible. The owner of the lot offers Will a job and Will accepts. It isn't long that Will is the best salesman on the lot and he's being considered for an executive position so he drops out of school.
Phillip's former girlfriend Janice visits, and Vivian is jealous and annoyed. Will likes Janice's daughter Wendy and flirts with her. However, Janice flirts with Will. Phillip finds out that Will and Janice slept together.
Will, in an attempt to impress Lisa, makes a photo of Jay Leno by night and sells the picture to an editor. However, Will doesn't know the editor works for a sleazy gossip magazine and ends up being sued for libel by Jay Leno.