Crandall Smythe (voiced by James Avery) is Oscar Proud's rival who holds a grudge against him for beating him in the Spelling Bee when he believes that he cheated back then in 1977. One day when Oscar runs into Crandall in the lobby of the Wizard Kelly Theater, he taunts him and calls him a loser and mocks him for his loss, causing Crandall to quit his job as a janitor and makes his son Timothy quit to so that he can get him into the Spelling Bee contest and beat Penny Proud as a way to get back at Oscar for his insults.
Next day, he and his son where in the Wizard Kids Learning Center telling Oscar that he was no longer working at the theater. When the clerk mentioned that he had only one brain power increaser left, he and Oscar fought recklessly over the toy and broke it!
On the night of the spelling bee, he was hoping that his son would win but when security caught Timothy cheating by Oscar's call, he was disqualified leaving Crandall shocked with dishonesty. After Penny won the Spelling Bee, he congradulates her and admitted to Oscar that he has a real winner on his side because of his son cheating. But when Penny says she cheated, Crandall, Oscar and Mr. Chang start fighting over the trophy like crazies.