Drake tries to make Josh cool by telling him to try out for the football team. Instead, Josh gets "murdered" and he ends up being equipment manager, which isn't cool. Later, when the one of the player gets sick by Josh's brownies, the coach depends on Josh to play center. So now Drake must help Josh become cool and at the same time not actually play.

Drake finds out Josh is great at pool or billiards as Josh calls it. Drake bets some kids, and takes advantage of Josh's pool skills and starts hustling people, by taking their money, shoes and other clothing/personal items. Now Josh has made the ultimate bet, and Drake's stuffed in the corner pocket.

Drake meets a smart girl from school named Michelle that he really likes. Now, Drake is not the smartest kid in school, so he gets Josh to teach him things to impress Michelle. But things go too far when he accidentally says yes to an offer of joining the Academic Team. Meanwhile, Josh has had enough with Megan's pranks and tries to get back at her.