It's Career Day at P.S. 118 and everyone seems to be getting paired up with somebody fun. Gerald gets to be a firefighter, Helga gets to be cop, Phoebe gets to be a construction worker, and Harold gets to be a pilot. Arnold gets paired up with the Jolly Olly Man, the local ice cream man who is "A stingy, mean spirited jerk who hates children and is constantly teetering on the brink of insanity."
Arnold's Career Day is off to a horrible start. First, Willie makes him sit in the freezer, then he says can't talk to the customers, or even accept money from the customers. Sooner, Willie's boss, who happens to be his father, arrives and says that if he doesn't sell his whole stock by 6:00, he will lose his job. Arnold learns about Willie's perspective and how much he hates working everyday. Arnold agrees to help him sell his whole stock, but only if Willie gives him a passing grade for Career Day.
Arnold teaches Willie to remember to treat his customers with respect, have a positive attitude, to keep his truck clean and neat, and that every customer matters.
Soon Arnold and Willie are down to half a freezer full. Arnold has an idea to go back to the school and wait for all the other kids and their partners for Career Day. Sure enough everyone wants some ice-cream and they sell out their whole stock just in time.
Willie keeps his job and gives Arnold a big fat F, as a joke. Arnold actually gets an A and learns that even the worst situations can turn out to be the best opportunities to help others. Willie's father then drives by and disapprovingly glares at Willie before driving off. Willie then yells after him and taunting "I'm the Jolly Olly Man! I'm stayin' right here!"
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