Sideways Stories from Wayside School

Sideways Stories for Wayside School


Sideways Stories from Wayside School 

In adapting Louis Sachar’s Wayside Schools novels for the theater, John Olive faced a huge challenge, what to leave out! This two act play captures the zaniness of Wayside School for the stage. The quirky, quick humor is appealing to children of all ages!

The Wayside School was supposed to be one story high, with 30 classrooms side by side; instead, it was built sideways, with 30 one-classroom stories. As befits such a strange school, these tales are a bit strange too. Maybe that accounts for the wacky goings-on in Mrs. Jewls’ class.

17 Characters: 10 Females – 7 Males

Run time: One Hour, 45 minutes


Sideways Stories from Wayside School  – Character list description

  • Gorf, the Meanest Teacher

Mrs. Gorf, the teacher on the thirtieth floor, has a reputation as the meanest teacher at Wayside School. She says if the students are bad or if they answer a problem incorrectly, she will turn them into apples. She turns four students into apples first, then eight more… When the children start to get Mr. Louis, to help, Mrs. Gorf tells them she will change them back into apples. Jenny holds up a mirror and Mrs. Gorf turns herself into an apple instead, leaving the students without a teacher. Louis comes upstairs, hungry, and eats the only apple in the room, which was really Mrs. Gorf.

  • Louis, the Yard Teacher – The Laid Back, Grown Up, Surfer Dude

Louis, the yard teacher, is  a reoccurring role throughout the show. He gets suspicious when the children do not show up for recess and goes up to Mrs. Gorf’s classroom. When he sees the apples, he decides Mrs. Gorf must be a good teacher because she gets so many apples. The next day, a dozen more children are turned into apples, and Louis goes up to Mrs. Gorf’s room again. Seeing twenty-four apples, he decides Mrs. Gorf is the best teacher in the world.

  • Jewls, the Sweetest Teacher – LEAD

The sweet and kind teacher follows the meanness of Mrs. Gorf.  Mrs. Jewls, who has been told she would be teaching “horribly cute children.” The students are also afraid because they have been told Mrs. Jewls is a “terribly nice teacher.” Mrs. Jewls walks in and decides all of the children must be monkeys because they were too cute to be children. The children try to tell her they are not monkeys, but Mrs. Jewls responds by saying they are simply too cute to be actual children. Finally, Mrs. Jewls believes them and starts teaching. Todd breaks the no talking rule and has his name written on the board under DISCIPLINE.

  • Dameon – Student, Reoccurring Character, “Counter”

Joe can’t count the number of hairs on his head. When he tries to count, his numbers are all out of order. Mrs. Jewls resolves to teach Joe how to count correctly. Time and again, the same thing happens. She has him mimic her as she counts to ten, then she sets six erasers on the desk for him to count. He counts in the correct order but fails to get the correct total. The other kids make fun of him for not being able to count. Mrs. Jewls tells Joe that it will just come to him one day, and he will be able to count. The following day, Joe knows how to count and knows how many hairs are on his head.

  • Myron – Student – Reoccurring Character, Stuck to seat with Gum, Class “Big Mouth”, “Pig tail puller”

Myron has the second biggest mouth in the class. Someone puts the wad of gum in his chair, and Myron gets stuck. Mrs. Jewls sends for some ice water from Mrs. Mush, who undercooks or overcooks everything. When she comes back, Mrs. Jewls pours the water over Jason, but Jason is still stuck. Someone asks if she would have to go home early if she could get Jason unstuck. She kisses him on the nose, and he falls to the floor. Joy erases her name.

  • Bebe – Student, Reoccurring Character, “Artist”

Bebe Gunn is the fastest draw in the class. Calvin is Bebe’s assistant, in that he puts her paper down and hands her the crayons. When Mrs. Jewls questions Calvin about not drawing any pictures himself, he responds by saying it would take him the whole period to draw just one picture, whereas Bebe can draw many that period when Calvin helps her. Mrs. Jewls says that a person could spend his whole life drawing just one picture of a cat and if that one picture is better than the two million Bebe could do, then that person has produced more art. Bebe is saddened by this and goes home to draw a picture of a cat, claiming she doubts she will be finished with even one whisker by the following day.


  • Leslie – Student, Reoccurring role, “Pig tailed girl”

Leslie has two pigtails that go all the way to her waist. Louis then offers her a dollar apiece for each of her pigtails. She asks him if he is crazy. Little does she know that her pig tails are taunting Myron.

  • Sammy, Student, Cameo Role

Sammy is the new kid in school. He comes in during a very rainy day, practically buried underneath multiple raincoats. He is very rude to the rest of the students, who comment that he smells terrible. Mrs. Jewls takes off Sammy’s first raincoat. The smell gets worse. She takes off Sammy’s second raincoat. The smell is overpowering. Sammy calls them all a bunch of pigs. His name is written on the board under DISCIPLINE. Mrs. Jewls removes the third raincoat and throws it out the window. This continues until Sammy is only two inches tall. With every raincoat removed, the smell gets worse and Sammy gets ruder. When the final raincoat is removed, all that is left is a dead rat. Dead rats were always trying to sneak into Mrs. Jewl’s classroom.


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