Crash and Wyatt go to extreme lengths to complete their community service hours in order to graduate to 8th grade. Running out of time, the two go to work for Roland who has been put in charge managing the annual "Portland Day" parade, but Crash's misguided efforts only sabotage their hard work.

Wyatt and Crash land a job at the local newsstand where Crash begins giving customers silly advice that somehow pays off. Crash becomes a local celebrity and even lands a book deal, while Mel tries to convince everyone that Crash doesn't know what he's talking about before things go too far.

Crash buys a trucker hat at a monster truck rally which he believes brings him good luck. When the hat goes missing Crash and Wyatt begin an investigation to solve the mystery.