Wayside School Fan Fiction

Wayside School Fan Fiction
_____W A Y S I D E - S C H O O L - F A N - F I C T I O N_____

Monday, May 11, 2026

Knowledge K

This story is inspired by Kathy’s attitude toward her classmates in the twentieth chapter of Louis Sachar’s Sideways Stories from Wayside School, as well as throughout the rest of the book. Before we dive into the fan‑fiction, let’s take a look at Chapter 20, “Kathy.”


CHAPTER 20. KATHY — SUMMARY

Kathy doesn’t like anyone in her class; not even Mrs. Jewls, whom she blames for misleading her about a pet tomcat named Skunks. Mrs. Jewls had reassured Kathy that the cat wouldn’t run away if she took good care of him, but he fled anyway. Kathy especially dislikes Dameon, who tried to teach her how to play catch. She didn’t move when he tossed the ball to her, and it hit her. She also dislikes Allison, who offered her a cookie. Kathy kept the cookie in her desk for weeks, and when she finally took a bite, it tasted like dirt. And that is why she doesn’t like anybody.




It was “happy Friday.” When the last bell of the day rang, Kathy slipped on her backpack and hopped out the classroom door. She almost bumped straight into Dana, who was standing frozen at the top of the stairs.

“Did you just turn into stone?” Kathy snapped. “Move aside, Dana, or someone might push you down the stairs!”

Dana quickly stepped left, pressing her back against the wall.

“Thank you, Kathy,” she gasped. “Actually, I have a question for you.”

Kathy frowned. “For me? What question?”

“I’m in the acting club, and we need one more person for a play we want to put on stage,” Dana explained. “I was wondering if you’d like to join us.”

“Why should I join you?” Kathy sneered.

“Because you’re one of the best students in Mrs. Jewls’s class,” Dana said. “You know a lot, and you have a strong personality. We have the perfect role for you.”

Kathy snorted. “Out of curiosity, who else is in this acting club of yours?”

Dana thought for a moment. “Bebe, Leslie, Paul, and Myron. But Myron doesn’t act—he’s very good at directing.”

“I bet he is,” Kathy muttered, trying not to burst into laughter. “And Paul? Is he supposed to pull Leslie’s pigtails again?”

“That was an accident!” Dana protested. “So, what do you say? Could you come to school on Sunday? We’re going to discuss our parts, and Myron will give us the text we’re supposed to learn.”

Kathy shook her head. “I have better things to do,” she said with a laugh, already heading down the stairs. “Good luck finding someone else.”

A black car was waiting outside the school. Kathy opened the door and slid into the back seat.

“You’re late,” her mother said as she pulled away from the curb. “Is something wrong?”

“No problems,” Kathy replied. “Someone offered me a part in a class play or something.”

Her mother glanced at her in the rearview mirror. “Do you plan to join the acting club?”

“No way,” Kathy chuckled. “I don’t have time for kids’ play.”

Her mother checked the clock on the dashboard. “I hope we won’t be late.”

Luckily, they weren’t. Traffic was lighter than expected.

The car stopped in front of a tall gate. Kathy’s mother rolled down the window, showed a special badge to the guard, and he nodded.

“The producer is waiting for you,” he said as the gate opened. He waved at Kathy. “Hi, K.”

Kathy didn’t wave back.

This was WDY Prime, a small TV station known for its game shows. For several weeks, Kathy had been competing in a difficult contest. Even though she was the only child contestant, she had made it all the way to the finale. Her stage name was Knowledge K, and everyone knew she had a real chance of winning the grand prize: one million dollars.

Tonight was the finale.

“You look just like a princess!” the producer exclaimed when Kathy stepped out of her dressing room.

Kathy smiled and gave a small bow. She looked adorable in her silver dress, complete with a sparkling tiara.

“Thank you,” she said.

She didn’t like the producer—he reminded her too much of her grandpa. But she knew she had to act nicely if she wanted that million dollars.

It was a long, exhausting night. But in the end, Knowledge K was declared the winner. Her mother rushed onto the stage and hugged her tightly. Kathy had won a million dollars.

There was almost no traffic on the way home. Her mother grinned at her in the mirror.

“We should celebrate.”

“Of course,” Kathy said. “But first let’s call the agent. I want to see the house again tonight.”

“You still want to buy that mansion?” her mother exclaimed. “I thought you were joking.”

Kathy snorted. “When do I joke?”

The agent was thrilled to meet them, even on a Friday night. Kathy and her mother signed the papers, and the house became theirs. It looked like a small castle.

Kathy spent the next day buying furniture and decorating every room. She hired a gardener to trim the bushes and plant more roses. She also told him to find a tomcat for her, and he said he knew just the one.

“You know you can’t live here by yourself,” her mother reminded her. “You’re still a child.”

“I just won a million dollars,” Kathy replied. “I’ll spend my weekends here and pretend I’m a princess.”

When Kathy returned to the mansion on Sunday, the garden looked perfect. The roses smelled heavenly.

She went inside to check on the tomcat in his special room—but he was nowhere to be found.

She called the gardener, who arrived as fast as he could.

“Where’s Skunks?” she demanded.

“Who’s Skunks?” he asked.

“I named the cat Skunks,” Kathy said impatiently.

“Does he smell?” the gardener asked.

“I don’t know!” she yelled. “I can’t even find him!”

After searching under every bed and behind every curtain, they finally found the cat hiding in a closet behind several shoeboxes.

“Take him back,” Kathy muttered, scooping him up and shoving him into the gardener’s arms. “He’s stupid.”


When the gardener left, she tried watching TV but got bored. She wandered through the house, then drifted back into the garden.

Suddenly she remembered Dana and the acting club.

She took a taxi to Wayside School and told the driver to wait. She ran to the playground.

Dana and Jenny were jumping up and down on the basketball court while Myron watched from a bench. Bebe, Leslie, and Paul were playing on the monkey bars.

“What kind of acting club is this?” Kathy mumbled.

She considered telling Myron to let Stephen direct the play—he was a better class president, after all. Or maybe she should encourage Paul to pull Leslie’s pigtails again. Leslie had the best scream Kathy had ever heard.

“Looking for something?” a voice said behind her.

“Oh my gosh!” Kathy exclaimed, spinning around. It was Louis. “My heart almost jumped out of my chest. Why are you sneaking around like that, Louis?”

“It seemed to me that you were the one sneaking,” Louis chuckled. “Are you planning something evil?”

“Why would I plan something evil?” Kathy blurted out.

“Because that’s what people do when they don’t like their friends,” Louis said. “They start doing bad things.”

“If you must know, Dana invited me to act in their play,” Kathy replied.

“Are you going to accept?” Louis asked.

“No way,” Kathy muttered, turning away. “I don’t have time for this.”

How to Turn Your Life Around

This story is inspired by Leslie’s dilemma in the eighteenth chapter of Louis Sachar’s Sideways Stories from Wayside School. Before we dive into the fan‑fiction, let’s take a look at Chapter 18, “Leslie.”


CHAPTER 18. LESLIE — SUMMARY

Leslie is puzzled by her toes, which she believes serve no useful purpose. At recess, Louis jokingly suggests that she sell them to him for five cents apiece. At first, Leslie finds the idea ridiculous, but the next recess she approaches Louis to see whether he’s still interested in buying her toes. By then, however, the yard teacher has become more selective. He only wants to purchase her big toes and says she can keep the smaller ones. Leslie insists on selling them only as a complete set, so the deal falls through.




Leslie’s family always celebrated Thanksgiving at Grandpa Jeff’s place. Since Grandpa Jeff had once been a chef, everything he cooked tasted amazing.

But last Thanksgiving was different from all the others. It started with Aunt Claire, who loved talking about “making changes” and “turning her life around.”

The moment they stepped inside Grandpa Jeff’s house, everyone froze. Aunt Claire had chopped her hair short and dyed it such a bright red that it looked as if she’d emptied a whole bottle of ketchup over her head.

“Oh my goodness, Claire!” Leslie’s mom gasped. “I almost didn’t recognize you.”

“Same here,” Leslie’s dad laughed. “You look like you survived an explosion in the tomato factory!”

“At least you noticed me this year,” Aunt Claire replied.

“What do you mean?” Leslie’s mom asked.

“Last year you thought I hadn’t come to Thanksgiving, and I was sitting right in front of you,” Aunt Claire said.

Leslie’s mom frowned. “I’m sorry, but I don’t remember that.”

“It’s fine,” Aunt Claire chuckled. “My boss says the same thing. He told me I’m nice and hardworking, but people forget I exist. So this year I decided to turn my life around.”

“By dyeing your hair red?” Leslie’s dad asked.

“That too,” Aunt Claire said. “We’ll see if it works.”


Grandpa Jeff called everyone to the dining room. The decorations were warm and cheerful, and the food smelled heavenly.

“I like Claire’s new look,” he announced. “And this year, I want us to stop arguing about how different we are. Let’s focus on what makes each of us special, without picking a fight.”

“What do you mean?” Cousin Vic asked.

Leslie shifted uncomfortably. Cousin Vic was her cousin, but he was also a grownup, which felt weird. But he was always nice to her and bought her the best presents.

“I mean,” Grandpa Jeff said, “I don’t want to hear that city life is better than country life, or which kind of weather you hate. Tell me what you like and how you plan to make your life better.”

Cousin Vic nodded while swallowing a meatball. “That makes sense.”

“Okay, I’ll start,” said Mr. Franklin Biddlecombe, Grandpa Jeff’s best friend. He wasn’t family, but everyone loved having him around. “May I?”

“Go ahead, Frank,” Grandpa Jeff urged.

“My home had become extremely cluttered,” Mr. Franklin Biddlecombe began. “So I decided to get rid of everything.”

“Everything?” Aunt Claire squeaked.

“Well, everything I didn’t use,” he clarified. “I sold my old magazine collection, tossed all the junk mail, and donated the clothes that didn’t fit, were out of style, or hadn’t been worn in a year.”

“That was most of your wardrobe!” Grandpa Jeff laughed.

“Exactly,” Mr. Franklin Biddlecombe said. “Then I emptied my garage: old paint, broken tools, dusty holiday decorations, cardboard boxes. Now I can finally park my car inside.”

Grandpa Jeff patted him on the back. “Nice. I should probably do the same.”

“That’s a great idea,” Cousin Vic said. “I started something similar a couple of months ago.”

“You emptied your garage too?” Grandpa Jeff asked.

“I don’t have a garage,” Vic replied. “But I used to be a bit overweight.”

“I noticed you look thinner,” Aunt Claire said.

“I joined a special military program,” Vic explained. “Two weeks in an army camp: regular meals, healthy food, lots of training.”

“You really turned your life around,” Grandpa Jeff said.

“You have no idea,” Vic chuckled. “When I got home, I got rid of my washing machine and dishwasher. Now my place is spotless, and I wash everything by hand.”

“That’s a bit extreme,” Aunt Claire said.

“I feel like a new man,” Vic insisted. “If you want to turn your life around, you have to make real changes.”

“True,” Aunt Claire agreed.

Later that evening, when Leslie and her parents got home, she made up her mind. She was going to turn her life around too. She wasn’t going to dye her hair red. Her pigtails were perfect. And she liked the way she looked.

But her toes were another story.

She had never known what to do with them. Her toenails were impossible to cut, and she hated trimming them. The spaces between her toes collected dirt and always smelled funny.

If she was going to turn her life around, she knew exactly where to start.

Sunday, May 10, 2026

The Blackboard Problem

This story is inspired by John’s problem in the seventeenth chapter of Louis Sachar’s Sideways Stories from Wayside School. Before we dive into the fanfiction, lets take a look at Chapter 17, John.

 

CHAPTER 17. JOHN — SUMMARY

John can only read books when they’re upside down. Since books aren’t printed that way, he has to flip them over himself. But Mrs. Jewls points out that he can’t turn the blackboard upside down. So, if John wants to read what she writes, he’ll have to learn to stand on his head. After several clumsy attempts, John finally manages it with the help of a few classmates. However, when one of them steps away to fetch a book, John loses his balance and falls flat on his face. When he recovers, he’s surprised to discover that he can now read the blackboard just like everyone else.




At first, everything seemed perfectly normal. John was one of the most active students in Mrs. Jewls’s class. He joined every activity, gave excellent answers, read better than almost everyone else, and always did his homework on time.

One day, Mrs. Jewls was solving a difficult math problem on the blackboard. It was a long line of tricky fractions, and the whole class was scrambling to  copy it down. That’s when she noticed something strange.

She stopped from writing and stared at John. He wasn’t copying from the blackboard at all. He was copying from Joe’s notebook—Joe, who was sitting behind him.

“Wait a minute, class,” Mrs. Jewls said. “John, what are you doing?”

John looked up. “I’m copying the problem from the blackboard.”

“No, you aren’t,” she said. “You’re copying it from Joe.”

John hesitated. “Sometimes I copy from Joe,” he admitted. “But mostly I copy from the blackboard.”

“Why do you need to copy from Joe at all?” Mrs. Jewls asked.

“Because I can’t always see the blackboard very well,” John explained. “But I can see Joe’s notebook better.”

“How can you see Joe’s notebook better?” Mrs. Jewls demanded. “It’s upside down.”

John shrugged. “I don’t know.”

Mrs. Jewls picked up a book and handed it to him. “Read a page for me.”

John’s eyes widened. “What page?”

“Any page.”

John opened the book slowly. His hands were shaking.

“You make me nervous when you watch me like that,” he said, dropping the book onto his desk. “Could you go back to the blackboard? I think I’ll feel more comfortable.”


“You read books upside down, don’t you?” Mrs. Jewls said.

John sighed, then nodded. “Yes.”

“How long have you been reading like this?”

“Since I was little. I’ve always read this way.”

“I suppose you also write upside down,” the teacher said. “How can anyone read your work?”

John shrugged again. “I just turn the paper upside down,” he muttered.

“Right,” Mrs. Jewls said. “Do your parents know about this?”

“Yes, they do.”

Mrs. Jewls glanced at the clock. “All right, class. You may go to lunch five minutes early today. We’ll meet again after recess.”

The children cheered and rushed out—everyone except John. He walked slowly behind them, hoping Mrs. Jewls wouldn’t force him to read right-side up from now on.

As soon as the room was empty, Mrs. Jewls called John’s father.

“I need to speak with you as soon as possible,” she said. “But I can’t leave the school now.”

“If the mountain won’t come to you, you must go to the mountain,” the man replied. “I’ll be there in five minutes.”

Mrs. Jewls met him on the first floor, in the administration office.

“It’s about the way John reads and writes, isn’t it?” he said.

“Indeed,” she replied. “When did you first realize he reads upside down?”

“Long before he could read,” John’s father said. “His mother noticed something unusual. John loved drawing, but he would sketch a boat and call it a house. Then he’d draw a cup and say it was a hat.”

“Interesting,” Mrs. Jewls murmured.

“It became obvious when he wrote an M and insisted it was a W, or scribbled a 9 and said it was a 6,” the man continued. “Now he’s great at puzzles because he can see pieces in any position. And he beats everyone at Monopoly because he can read the board upside down.”

“Do you know why he’s different from the other children?” Mrs. Jewls asked.

John’s father shook his head. “No idea. His vision is perfect.”

“I thought so,” Mrs. Jewls said. “That means it must be his brain—and we can’t mess with a child’s brain.”

“Absolutely not.”

“The problem is he can’t read the blackboard,” she declared. “I’d like your permission to try some new methods. Nothing that will affect his brain.”

John’s father thought for a moment. “I don’t see why not. As long as it doesn’t involve messing with his brain.”

“Not at all,” Mrs. Jewls promised.

“Good,” he said, standing. “I must return to the office. We’ll keep in touch.”

As the man left, Mrs. Jewls considered John’s problem. 

We can’t turn the blackboard upside down, she reasoned. If the mountain won’t come to you, you must go to the mountain. That means John will have to learn to stand on his head.

She hurried up the stairs to the thirtieth story, excited that she had found a solution.

Saturday, May 2, 2026

Minimalism

This story is inspired by Rondi’s situation in the thirteenth chapter of Louis Sachar’s Sideways Stories from Wayside School. Before we dive into the fan‑fiction, let’s take a look at Chapter 13, “Rondi.”


CHAPTER 13. RONDI — SUMMARY

Rondi is missing her two front teeth, and suddenly everyone thinks those missing teeth are the cutest things in the world. She can’t understand why. After all, something that doesn’t exist can’t be cute or beautiful. Her classmates start teasing her by complimenting outfits she didn’t wear and laughing at jokes she never told. When she finally tries to tell a real joke, no one pays attention. At recess, she runs outside only to be stopped by Louis, who wants to see her adorable front teeth. She screams and punches him in the stomach. 



It was a late autumn, foggy morning. When Mrs. Jewls entered the classroom, she looked tired and a little gloomy. She squinted at the cloudy sky outside the window and the gray buildings fading into the mist.

“Why didn’t you turn on all the lights this morning?” she asked Stephen.

Stephen blinked. “I did! I turned on every single one.”

“You’re right,” Mrs. Jewls muttered, glancing around. “But the room still looks boring and sad. How can we work in an environment like this?”

“We can’t,” Terrence agreed. “Shall we call it a day and come back tomorrow? Maybe the weather will improve.”

Mrs. Jewls wagged her finger at him. “Nice try. No, I mean, can’t we do something to make the classroom look better?”

Todd scratched his head. “I don’t know. Should we clean it again?”

“The classroom is clean,” Mrs. Jewls said. “Cleanliness isn’t the problem. The problem is that it doesn’t look enjoyable, does it?”

“That’s why I prefer the kickball field,” Todd said. “It looks like you can do anything you want out there.”

“Okay, class,” Mrs. Jewls announced. “I need a volunteer to decorate the classroom so we can actually enjoy being here. That way I can teach better, and you can have fun while you learn.”

Todd’s and Terrence’s hands shot up at the same time.

“I raised my hand first!” Terrence shouted.

“No, you didn’t,” Todd said, even though he hadn’t looked at Terrence at all.

“Maybe you two can work together,” Mrs. Jewls decided. “And Louis can help you. He has access to the workshop behind the school.”

When school let out, Todd and Terrence were ready. They weren’t thrilled to work together, but they had no choice.

“Okay, boys,” Louis said, patting them on the back. “What’s your design idea?”

Todd and Terrence stared at each other.

“What does ‘design’ mean?” Terrence asked.

“I mean, what’s your plan for how the room should look?” Louis explained.

“I thought you were going to tell us how it should look,” Terrence muttered.

“Guys, use your creativity,” Louis urged. “What do you like?”

“Dinosaurs,” Todd said.

“Pyramids,” Terrence said.

“Pyramids?” Louis and Todd exclaimed.

“Pyramids are big and strong,” Terrence declared. “And they look perfect.”

“We’re not turning our classroom into a pyramid,” Todd grumbled.

“At least I have a design idea,” Terrence said. “What do you have? Dinosaurs?”

They worked all afternoon. By the time they left, Louis had helped them build several tall columns and a huge chair at Mrs. Jewls’s desk, something that looked like a pharaoh’s throne.

Mrs. Jewls nearly screamed when she walked in the next morning.

“Oh my gosh!” she gasped. “Did ancient Egyptians invade our school?”

Todd shrugged. “Terrence insisted. He thinks pyramids look perfect.”

“They looked perfect,” Mrs. Jewls agreed, “but I don’t feel like teaching in here anymore.”

“Shall we call it a day and come back tomorrow?” Terrence suggested. “Maybe you’ll get used to it.”

“No,” Mrs. Jewls said. “I need someone else to come up with a better design. Who can think of something more appropriate?”

Joy’s and Maurecia’s hands shot up.

“You two are best friends,” Mrs. Jewls said. “I’m sure you’ll create something better, with Louis’s help of course.”

After classes, Louis arrived again.

“I hope you have a clear design plan,” he said. “What do you girls like?”

“I love flowing lines,” Joy said.

“And I like natural shapes,” Maurecia added.

Louis nodded. “Art Nouveau, then.”

The girls exchanged confused looks.

“Let’s use plants and flowers,” Louis explained.

The girls smiled. They placed big pots of green plants and colorful flowers around the room. They draped long vines over the columns Todd and Terrence had built. By the time they finished, the classroom looked like a friendly jungle, or a very wild garden.

Mrs. Jewls was stunned the next morning. At first she wasn’t sure where she was. Then she nearly tripped over backpacks and outstretched legs as she tried to reach her desk. It took her fifteen minutes to get to the front of the room.

“This is not going to work,” she sighed.

Terrence raised his hand. “Can I say something?”

“No, Terrence,” Mrs. Jewls said. “We are not calling it a day and coming back tomorrow. I need someone to create a different design or I’ll never be able to teach in here again.”

“Hurray!” Terrence cheered.

Everyone glared at him.

“Any volunteers?” Mrs. Jewls asked.

No one raised a hand.

She rubbed her chin. “All right, Stephen. You’re class president. I want you to work with Louis and fix this room. We can’t work like this.”

“But I’m not good at interior design,” Stephen protested.

“Then I’ll have to appoint someone else class president,” Mrs. Jewls said.

Stephen hoped inspiration would strike before Louis arrived, but it didn’t. He had no idea what to do.

“What’s your plan?” Louis asked when he walked in.

Stephen looked around at the chaos. “First, let’s get all these plants and flowers out. It’s getting stuffy in here.”

They carried everything to the school garden.

“What now?” Louis asked.

“The columns and the giant throne have to go,” Stephen said. “They make the room feel like a tomb.”

They hauled everything to a storage room in the basement. Then they wiped the blackboard and cleaned the classroom carefully.

“Are we finished?” Louis asked.

Stephen scratched his head. “I think so. We’re left with the blackboard, the desks, and the chairs. What do you call this style?”

“Minimalism,” Louis said.

“Perfect,” Stephen replied. “Minimalism it is. Let’s go home.”

When Mrs. Jewls entered the classroom the next morning, she smiled brightly.

“It’s amazing, Stephen!” she exclaimed. “Now I can finally teach.”

All the students agreed. They could finally learn too.

All except Terrence.

“The room looks exactly the same as it did at the beginning,” he said, but nobody listened.


Knowledge K

This story is inspired by Kathy’s attitude toward her classmates in the twentieth chapter of Louis Sachar’s Sideways Stories from Wayside Sc...