The Whipping Boy by Sid Fleischman is a fast‑paced, humorous historical fiction novel set in the late eighteenth century. The story follows Prince Horace, better known as Prince Brat, whose constant mischief goes unpunished due to royal custom. Instead, Jemmy, a poor orphan boy, serves as the prince’s whipping boy, receiving the punishment meant for Horace.
Bored with palace life, Prince Brat forces Jemmy to run away with him in search of adventure. Their escape quickly turns dangerous when two cutthroats capture the boys, hoping to ransom the prince. As the pair face trouble in the countryside, Jemmy’s street smarts and the prince’s growing humility begin to shift their relationship. What starts as an unfair arrangement becomes an unexpected friendship forged through danger, courage, and quick thinking.
This Newbery Medal–winning novel is perfect for upper elementary readers and works beautifully for lessons on character development, theme, historical context, and problem‑solving.
⭐ Book Details
- Publication Date: April 1986
- Reading Level: Lexile 570L • Guided Reading Level R
- Interest Level: Grades 3–8 (Ages 8–12)
- Awards: 1987 Newbery Medal
- Length: 96 pages (approx. 29,280 words)
- Estimated Reading Time: About 1 hour and 57 minutes
- Genre: Historical Fiction
- Setting: Countryside surrounding a royal castle in the late eighteenth century
- Themes: Responsibility, Adventure, Boredom, Friendship, Social Class
- Point of View: Mostly third person
- Memorable Quote: “Was it clothes that made a prince, Jemmy wondered, just as rags made a street boy?”
- First Line: “On a night when the moon gazed down like an evil eye, the young prince appeared in Jemmy’s chamber.”
The Whipping Boy Activities
The Whipping Boy Book Unit Samples
This sample contains vocabulary practice, a comprehension quiz, and a constructed response question for Chapters 1-2.
Teaching Idea #1 ~ Anchor Charts
The day before beginning The Whipping Boy, I displayed the following anchor charts in the classroom. These stayed up for the duration of the novel. As students read, we added character traits. Once we had read approximately half the book, the characters’ main problems were added. At the end of the novel, the solutions to these problems were also added.
Teaching Idea #2 ~ Newbery Medal Winner
The Whipping Boy won the Newbery Medal in 1987. Have students research to learn about the Newbery Medal.
Facts:
- The Newbery Medal was established on June 22, 1921.
- The Medal is given annually by the American Library Association.
- The award goes to an American children’s book published the previous year.
- The runners-up are called honor books.
- Winners are selected by a committee of the Association for Library Service for Children.
- Winners receive $10,000. Finalists receive $1000.
- Winners are announced in the fall.
Things to Do:
- Have students research to determine which authors have won multiple times.
- Create a class list of Newbery-winning books students have read.
Teaching Idea #3 ~ Book Covers
Have students compare different book covers to determine which best represents the story. This webpage shows six different covers for comparison.
Teaching Idea #4 ~ The Whipping Boy – Full Movie on YouTube
In 1994, The Whipping Boy was turned into a full-length, 1 hour and 43 minutes, movie. This is one film you don’t have to worry about. It’s G-rating makes it perfect for classroom viewing. With more than a hundred ratings, the movie has an 81% likability score.
Comparing the book to the movie is a great learning activity for students. In this instance, the movie follows the major elements of the story. The film adds several new characters making it an interesting comparison. Look for Annie Rose, Blind George, and Queen Mum in the movie.
Teaching Idea #5 ~ On the Web
On the RIF website, you’ll find memory games, crossword puzzles, and word searches. These interactive activities are great fun for students and greatly improve vocabulary skills.
You’ll find great discussion questions, vocabulary exercises, and character traits at the Appalachian State website. The book is divided into three sections with activities for each. Click the links below to go to each section.
See the product that inspired this post.
The Whipping Boy Novel Study includes vocabulary practice, comprehension questions, constructed response writing, and skill practice.
