It's Career Day at P.S. 118 and instead of listening to lectures, the kids are to visit a workplace by taking a job from a basket. Then all types of different occupations walk into the classroom including a Mailman, Construction Worker, Firefighter, Police Officer, A Fisherman, A Meat Butcher, A Doctor, and much more! 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 alongside Ernie Potts and Harold gets to be a pilot. Arnold, however, gets paired up with the Jolly Olly Man, the local ice cream man who is "A stingy, mean-spirited jerk who hates kids 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 Arnold can't talk to the customers, or even accept money from them. Soon, 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 every day. 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 neat and clean, 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 playfully yells after him by taunting "I'm the Jolly Olly Man! I'm stayin' right here!".
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