Hilarious Short Stories To Teach in Middle and High School

It usually occurs that every new academic session, at least one freshman would ask me why our reading texts in 9th grade English werewere so frustrating. A check at our curriculum reaffirmed that they did have a point. Books like “Romeo and Juliet,” and Mice and Men..Short tales like “Lamb to the Slaughter,”- these stories and more told of death and despair. No doubt these books are great, but I have come to think of adding different texts to the ones already available. Stories of despair seem easy to find, while fun-cracking ones are tricky to trace.     

Having these in mind, we have a list of short stories that can bring amusement to your lesson. 

  1. Charles by Shirley Jackson

Authored by the same woman who wrote the eerie short tale, “The Lottery,” this story is capable of making students of all ages chuckle. The story of the inferior kindergarten student ever, as shared by a student in the same class as his mother at the close of every school day, students will fall in love with this Charles’ exciting book.   

In class: Quite great for lessons on irony, your students can discuss if Jackson’s funny short story shows situational, verbal, or dramatic irony. I’ve deployed this same story to show how an author can make use of dialogue as a means of building characterization.

  1. Thank you, M’am by Langston Hughes

Like “Charles,” this is also a classic, renowned story. An older woman housed a young man under her roof after he had tried stealing her purse. All the time spent together, the elderly would teach this young man a valuable lesson about life—an ideal book for upper-elementary and middle schoolers.     

In class: This amusing short story is rich with lessons on diction, theme, dialogue, and characterization. Additionally, it would be a good text for Socratic seminars. Students could easily generate questions about the actions of the characters. They also could consider how they would have reacted to the same circumstances. 

  1. Lord Oakhurst’s Curse by O. Henry

Many students will have read “The Gift of the Magi,” but this story by the same author is not as popular. While Lord Oakhurst lay on his deathbed going through his final moments, with his wife grieving by his side (if that’s true), a doctor comes in to help. Your students will be caught by surprise by all of this book.     

In class: In the book’s foreground, there is an indirect characterization as students can discuss if Lord Oakhurst’s wife is really sad, as seen in the story. The story also employs flashbacks, making it awesome for introducing or reviewing that concept. 

  1. Maddened by Mystery or The Defective Detective by Stephen Leacock

This story characterizes the classic detective cliche and shames it badly. Mistaken identities and an absurd reveal make this story a funny one to share with your students.    

In class: I wish I still had the chance to teach the mystery unit I taught for years so that I could put this joyful story into the mix. A great piece to introduce satire. This story condemns virtually all concepts of an average detective story in a funny fashion. 

  1. Machiavelli in Kindergarten by Peter Schooff

This one is for older students; this story got me laughing uncontrollably. It was written as a series of caring emails from a kindergarten educator to the parents of little Niccolò Machiavelli. The news of his ambitions to remove his teacher and replace her with the school janitor are abnormal.  

In class: I doubt The Prince is still adopted in many English or political science classes. It will be a great accompanying text if it’s still the case. It would also serve as a combined text for nonfiction studies about Machiavelli. Just as the word “Machiavellian” often appears in news reports, it could also be employed as a vocabulary unit. Finally, the educator could use it to tell students that storytellers can write stories in various formats. Tell your students to try to imagine an email exchange between their preferred characters and a teacher or neighbor and see how it might look. The outcome might be funny. 

  1. Joy by Anton Chekhov

In this exciting short story, the main character surprisingly found fame and ran home excitedly to inform his family. Your students will admire how his surprised family reacted to the news. The protagonist’s eventful new stardom will also generate discussion among your students.      

In class: This book is best for characterizing tragic heroes. Chekhov’s work is a blistering commentary on the thoughts of what being famous means. Your students will have plenty of time to compare the protagonist and the several YouTube or TikTokers of today. 

  1. A Dish Best Served Cold by Tristan Jimerson

Are you familiar with The Moth? This organization aims to promote storytelling’s art and craft and honor and celebrate the diversity and commonality of human experience. They are blessed with open-mic storytelling nights in various cities all over the country, where people get up to tell stories based on a prepared theme. You’d see many of them on the Moth’s website and YouTube channel. 

This story is about a man whose identity was stolen by a Domino’s Pizza employee. His plans for revenge will hook you and your students with laughter.     

In the class: Many of these stories feature strong language and are adult-themed, so be determined to preview the story before sharing it with your classroom. The idea of sharing verbal storytelling with students of all age groups is awesome. It makes it beautiful for reluctant readers or assessment options. 

  1. The Catbird Seat by James Thurber

This story is about a sad man who dreamed of improving his life. His method of accomplishing this is hilarious and shocking.     

In Class: Intimating students to challenging text can be difficult, so it’s great to have a few short stories to brace students for what is ahead. Students can ask questions about parts that are not clear to them and work in hand to develop comprehension. 

  1. “I’m a Short Afternoon Walk, and You’re Putting too Much Pressure on Me” by Emily Delaney

I enjoy introducing my class to examples of writings happening in our world today. While many stories on this list are dated to the early 1900s, this one was written in 2020 and featured in McSweeney’s Internet Tendency. This site consists of humorous works on various timely topics.   

Although many of them aren’t fit for the school, some others, like this one, are ideal examples of how people are still going about writing and creating today. This personified piece, “afternoon walk,” tells the person taking it that the walker can’t just be everything.  

In class: Perfect for older middle school and high school students. This would be a mentor text for me. Think about the creative writing pieces students could develop if told to personify something in their lives.  

  1. My Financial Career by Stephen Leacock

I don’t particularly appreciate ordering food via phone. It’s not whether it’s healthy or not if I’m ordering it on behalf of one or twenty people. I wouldn’t say I like it. I became gutted and could misbehave. So is this story about a man who is usually nervous in the bank. Leacock’s description of the main actor clumsily finding his way through creating a bank account got me laughing.    

In class: Getting past characters that students can familiarize themselves with is tricky. I love it when I ask students to write about situations that make them troubled. After reading this story, they could write their descriptions, feelings, and images. 

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