The Best and Most Hilarious Sideways Stories

In Sideways Stories From Wayside School, there are thirty short stories full of wackiness. Let’s take a look at some of the best short stories among them.

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"Sideways Stories From Wayside School" on notebook paper.

When Wayside School was built, instead of being one story tall with thirty classrooms on that story, the school became thirty stories tall with one classroom on each story. That’s only the beginning of the weirdness of this school. Sideways Stories From Wayside School by Louis Sachar tells thirty stories about the different children and teachers in the classroom on the thirtieth story of this school. Each character has some weird personality traits and habits, but that is what makes them entertaining. Some characters may be exaggerated versions of people you know in real life. Some stories in this book really stood out to me and I want to highlight them. The following stories are some of the best ones from Wayside School.

Mrs. Gorf

One of the most fun parts of this book is the very beginning, when we meet the students’ original teacher, Mrs. Gorf, before the lovely Mrs. Jewls. We have all had one of those mean teachers. These are the teachers who always seem to have it out for the students and seem to thrive off of punishing them. That’s Mrs. Gorf, except she is a little more sinister than the average teacher.

Apple on a back background with a wonky white pattern.
IMAGE VIA BOOKSTR/RACHEL ROSENFIELD

Whenever a student acts out, Mrs. Gorf turns that student into an apple. Be warned, it’s not too difficult to cross Mrs. Gorf. Eventually, all the students turn into apples and plan to take Mrs. Gorf down. The next time she tries to use her powers, the students face a mirror of her, which turns her into an apple and saves all of the students. The story takes evil teachers to the extreme and perfectly introduces readers to the madness that occurs at Wayside School.

Maurecia

Who doesn’t love ice cream? While the answer may be that everyone loves ice cream, no one loves it more than Maurecia. Maurecia eats ice cream every day, a new flavor every time. However, at a certain point, Maurecia tries all of the flavors of ice cream, so ice cream is no longer interesting to her. It’s the worst fate that can fall upon a child. Mrs. Jewls decides to fix that by making new ice cream flavors for everyone.

Bowl of different types of ice cream on a orange-ish pink background.
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The first flavor is the Maurecia flavor. The flavor is supposed to be what Maurecia tastes when Maurecia tastes nothing. So, is this ice cream mouth-flavored? It’s best not to question it. Mrs. Jewls makes these flavors every day, one for every student. Everyone likes the Maurecia flavor, probably because her mouth is so used to ice cream, and Maurecia likes the Todd flavor and starts trying to taste him. The story shows what can happen when someone has a deep craving, the excitement of something new, and weirdly makes you think of your own ice cream taste.

Paul

Have you ever gotten distracted by the person sitting in front of you in class? Maybe their hair got in the way, and they couldn’t focus on the teacher. That is the case for Paul, who can not stop staring at the pigtails of Leslie, the girl in front of him. There is nothing particularly fancy or distracting about these pigtails; they are just so fascinating to Paul that he always feels a deep need to pull them roughly.

A girl with pigtails on a green background.
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The problem for Paul is that Leslie always screams when Paul pulls her pigtails. Who could have seen that coming? Whenever Leslie screams, Paul gets a strike on the board, and three strikes mean that Paul gets detention. Eventually, Paul comes up with a plan to pull each pigtail only once, so that he only gets two strikes and will not get detention. However, Leslie rats out Paul and screams even when he does not pull to get him in trouble. The lesson here is to respect people’s personal space and that pigtails can be a dangerous tool for a girl to own.

Sammy

The introduction of a new student is often an exciting time. It is a brand new person in your world starting off with a clean slate. Unfortunately, it was not such an exciting time when Sammy was the new student. He literally did not have a clean slate, as he smelled disgusting. Also, Sammy was wearing what looked like a million coats, and students could barely see his face. It only got weirder from there.

Person in a big coat on a dark gray background.
IMAGE VIA BOOKSTR/RACHEL ROSENFIELD

Since the students could not take the smell, Mrs. Jewls was left with no choice but to dispose of each coat. As she does this, Sammy insults everyone in the class and displays aggressive behavior. This new student is certainly not one that the other students like. It takes Mrs. Jewls a while to get rid of all of the coats, as Sammy is wearing so many. Once all of the coats are gone, all that is left is a dead rat. That’s right, Sammy has been a dead rat this whole time. The classroom has had a dead rat problem for a long time, and Sammy is just one of many that have been trying to get in. At the end of the day, you have to applaud Sammy the Rat’s creativity.

DeeDee

Every child wants to have a nice and shiny toy. After all, it is what will lead to the most fun, so a child may do anything to get that toy. At Wayside School, that toy is the green ball, and DeeDee wants it more than anything. There are three types of balls at recess. There is the green ball, which can bounce as high as the sky. There is the red ball, which is still a fairly decent bouncer. Then there is the yellow ball, which can barely bounce at all. Since DeeDe has to run all the way from the thirtieth floor to the playground for recess, she is always stuck with the boring yellow ball. DeeDee wants to change that.

Green ball on a sky background
IMAGE VIA BOOKSTR/RACHEL ROSENFIELD

DeeDee keeps doing whatever it may take to get to that ball first, but nothing seems to work. After all, thirty floors is a lot. The children in this class should be high-class athletes at the end of the school year, honestly. DeeDee is not giving up despite the setbacks. One day, she comes up with a brilliant plan. She is going to disguise herself as a dead rat so that Mrs. Jewls will think she is one and throw her outside early. In this world, that plan makes sense, and it works. DeeDee gets to be outside earlier and she finally gets to play with the coveted green ball. She proves that if you set your mind to your dreams, they can come true even if that dream involves being a believable dead rodent.

Kathy

If there is one thing to know about elementary school students, it is that they can be really stubborn. That is because they think they know everything. That is certainly the case for a student named Kathy, who hates everything. That’ss not an exaggeration; Kathy truly hates everything around her and everyone she meets. She liked Sammy, but as previously mentioned, he was a dead rat.

Angry girl on red background.
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Usually, Kathy’s hatred comes from incidents that she causes. She hates Mrs. Jewls because she was wrong about Kathy’s cat not running away. However, Kathy locked the cat in a closet for three weeks, so it makes sense that he ran away once freed. She hates a girl named Allison because she does not like a cookie that Allison made. Kathy did eat the cookie three weeks after it was baked, but that logic does not work on Kathy. The story ends with the narrator surmising that if Kathy met you, she would probably hate you, too. The cynicism can be relatable, so who are we to fault Kathy for calling out the world as she sees it?

Three Erics

Since names often follow trends of popularity, you are bound to have multiple children with the same name in your class. Perhaps you were that child who had to share a name with someone in your class, leaving you with a fate of lacking individuality. That is the fate of the Three Erics. It is the only story in the book that follows multiple children, which further emphasizes the point that the Three Erics can not be their own person. There is Eric Bacon, Eric Fry, and Eric Ovens. The other students in the class do not take the time to differentiate them, leading to assumptions that all Erics have the same traits.

Three young boys on a yellow background.
IMAGE VIA BOOKSTR/RACHEL ROSENFIELD

For example, Fry and Ovens are overweight, but Bacon is really skinny. However, since the other two Erics are overweight, the other students treat Bacon like he is overweight. Bacon and Ovens are bad at sports, but Fry is fantastic. However, everyone acts like he is bad too. Finally, Bacon and Fry are mean, but Ovens is really nice. As you can expect by this point, the students act like Ovens is mean too. It is a challenging experience for the three Erics, but nevertheless, that is the life when your parents pick a really common name.

Louis

We end the story with our friendly janitor, Louis. Louis appears frequently in other stories of the book, but now it is time to hear his story. The only thing is that his story is not about himself; it is about more students. He comes to Mrs. Jewls’ class to say hello to the students and tell them a story about another school of students. The stories are wilder than anything the thirtieth-floor students have ever experienced.

A drawing of a man reading to three students on a blue to yellow to orange-ish red background.
IMAGE VIA BOOKSTR/RACHEL ROSENFIELD

In the story that Louis tells, the students have never gone on outrageous adventures. Their ice cream is always normal, dead rats don’t appear disguised, and students never become apples. This story is shocking to Mrs. Jewls’ students and they are terrified. Mrs. Jewls chides Louis for telling a fairytale as these students that he talks about could certainly not be real. This last chapter serves as a meta-story, as it appears that their Louis could be our Louis, Louis Sachar. After all, the events of Wayside School are so weird that they could never be true. Right?

The wackiness of this collection of short stories is why it has been a classic for over forty years. Children everywhere have dived deep into these stories because they love imagining what it would be like to live in this weird reality and go to school on the thirtieth floor. It is a world with just the right amount of ridiculousness to make the stories exciting yet with some lessons relatable and useful. It takes a true talent like Sachar to weave that world. Also, if you can not get enough of the students from this book, you can read more about them in Wayside School is Falling Down, Wayside School Gets a Little Stranger, and Wayside School Beneath the Cloud of Doom. Trust me, it only gets more outrageous from here.


If you want to learn some more lessons from Louis Sachar, click here.

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