Chris convinces his father to accompany him to the father-son competition at the annual newspaper boy picnic.

Sharon's sister, Charleen, comes to visit and she is taken with Chris' charm, much to Sharon's chagrin.

Chris tries to raise money to help save a playground, so he tries to set a world record by having the most things piled on top of him.

The newspaper fires all the paper boys and replaces them with the Paperboy 2000, a paper delivering robotic vehicle, so Chris challenges it in a paper delivering contest.

There's a new waitress at the local diner, and Chris wants to take her out, but he needs to drive a car for the date. His problem is he never got a license.

Chris becomes a house sitter in an old Victorian house that appears to be haunted.

While delivering papers in the bad side of town, Chris meets a group of young hoodlums and he decides to ""take back the streets"" by helping the kids.

Much to Sharon's dismay, Chris auditions for and gets the lead part in a local community theatre production of Andrew Todd Keller's musical Zoo Animals on Wheels.

Chris finds proof that makes him think he is adopted, so he sets off to find his natural parents, an Amish couple.

Chris goes to work for the police in a sting operation after he buys a counterfeit watch, the Chrono-Sync 2000.

At the family reunion Chris is still struggling to get out from under the shadow of his cousin.

Chris wins a weekend with his favorite talk show host, a contest the host first regrets he agreed to, but later Chris regrets he entered, when the host decides to stay.

After destroying her kitchen, Chris becomes Sharon's slave to work off the $2000 in damage and she also breaks his will.

During one day, Chris meets his soulmate, marries her and goes through an entire relationship with her.

Chris and Larry join Mr. Peterson on a camping trip, when Mr. Peterson manages to lose them, the hungry boys eat some berries that cause them to hallucinate.

Chris becomes a construction worker with the men who are renovating his parents kitchen. When they tell him one of their trade secrets, Chris has a problem with their dishonesty.

Chris loses his wallet in the big city, and the big city give him the key to the city and other perks to make him feel better.

When Chris was 12 he got a job as a paperboy so he could buy a submarine from the back of a comic book. Four to six hundred weeks later when the kit arrives, Chris and his father put it together; however when they embark on the sub's maiden voyage (in Chris's bathtub) they become trapped.

Chris and Larry ignore an Indian curse and wind up switching places.

Chris has a near death experience and is endowed with prescience and he sees a vision of Sharon being murdered.