It is loosely based on the Wayside School books by Louis Sachar, and several elements differ between the two works.

At Wayside, every floor appears to have lockers, stairs, classrooms, doors, and light fixtures.

To add to the school's Escher-esque style, all of the features of the floors—doors, lockers, stairs, etc.—are placed in very unusual ways, as seen in the Escher artwork, Relativity.

Mush but was later evicted from the school due to his obnoxious demeanour; Mr. Blunderbuss (voiced by Dwayne Hill), the adventurous fourteenth-floor teacher who often goes on hunting safaris throughout worldwide jungles; and Miss Zarves, the nonexistent teacher on the nonexistent nineteenth floor.

However, due to his failure to cope with the school's unorthodox system of learning, Mrs. Jewls writes his name on the chalkboard and puts a check mark next to it, warning him that if another outburst will result in him getting sent home on the kindergarten bus.

Meanwhile, due to faulty wiring, a trash compactor installed on the 30th floor activates whenever Principal Kidswatter uses the PA system.

After discovering Wayside's blueprints in his "welcome binder", Todd tries to explain that the classroom is in fact a trash compactor, but is dismissed and sent home again.

Meanwhile, Myron makes a speech on the PA, causing the trash compactor to activate once again, only this time the class notice it and start to panic.

Todd sneaks back into Wayside and tries to find a way to free his class, while Louis stops Myron from continuing his speech, deactivating the trash compactor.

"Mad Hot": Principal Kidswatter challenges another school for the annual Wayside dance competition.

Todd decides he would do anything to prove that he will not be her boyfriend, so he eats Mush's mushroom surprise, that makes him fall in love with Mrs. Jewls.

"Music Lessons": Myron discovers a strange nose flute called the Strumplefloozle, and uses it to control his friends.

Later Myron finds out that Louis did indeed graduate, as he found his real folder when he was in Mr. Kidswatter's filing cabinet.

When Dana bumps Jenny's bike onto the ramp, it comes back, only with the seat signed by Mrs. Zarves.

One day, Myron receives a note saying Kidswatter is to be challenged to a game of Parkour with the chef.

Miss Mush suddenly asks Myron, Dana, Maurecia and Todd about their future careers.

Telling Maurecia, Dana, and Myron about the fake myths, Todd, with a snorkel over his mouth, dives in a can of beans, and comes out, speaking in a muffled voice.

So, Todd, Myron, Dana and Maurecia try to help crying John get right-side up, just like the kids who are parallel and are upside down.

In the end, Mrs. Jewls tells John, without the help from Todd, Maurecia, Dana, and Myron, that being upside down is not a bad thing.

Leading to an hour-long television special pilot titled Wayside: The Movie that aired in 2005.

[7] In 2018, the entire show and the pilot were released on Keep It Weird's YouTube channel, in wide-screen 16:9 for the first time.

David Cornelius of DVD Talk described it as "a clever, often hilarious little show that demands a larger audience", praising the series' scripts and dialogue as "delight[ed] in mixing absurd humour with fond grade school memories".

[8] Adam Arsenau of DVD Verdict stated "The most satisfying part of Wayside is how the show feels perfectly balanced—it has enough wacky antics and bizarre events to satisfy young audiences, enough logical fallacies and defiant attitudes to amuse middle-aged kids, and enough clever and sardonic wit to please adults fortunate enough to find themselves in front of a television set while the show is playing", concluding that Wayside was "the perfect cartoon adventure for families of all ages".

Alyse Wax of Blogcritics negatively compared the animated series to the books that inspired it, stating that "the series 'doesn't have the magic that the books had', and noting that while the books provided 'wacky, silly, with odd, funny, almost-realistic-but-not-quite characters', viewers get no such character development from the animation, and expanded that while the show is shared from an adult perspective, it is not meant to be enjoyed by parents and kids" watching it together, being "geared towards younger kids".

[11] Joanna Weiss of Boston Globe offered that while viewers familiar with the character development in the book series will see that the animated series "understandably, dispenses with the nuance in favour of kid-friendly slapstick and goofy conceptual jokes", the children and parents who have not previously encountered the books "won't know what they're missing".

[12] Michael P. Dougherty II of Fulve Drive-In gave a negative assessment of the series, describing it as "a disgrace to the novels" and believed it "totally strips away any intelligence or meaning they had".

[14] In 2008, Wayside received a nomination for "Best TV Series for Children" at the 2008 Cartoons on the Bay award ceremony.

[16] Maurecia's personality also diverges from that of the series—in the books, she is a normal girl with a love for ice cream who is never mentioned nor depicted to wear roller skates and is almost always featured with her best friend Joy, who never appears in the series.