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Leonardo, the Terrible Monster

by Mo Willems


This story explores questions about the nature of fear and the relationship between responsibility and desire.

Leonardo, the Terrible Monster is the story of Leonardo, a monster unable to scare people. When he is unable to scare the biggest “scaredy-cat” in town, he is able to realize that being a friend to someone is more important than being a monster, and that friends accept you for all you have to offer.

Read aloud video by AHEV Library

Guidelines for Philosophical Discussion

The most dominant philosophical issue in Leonardo the Terrible Monster is philosophy of mind, regarding the nature of fear and the relationship between responsibility and desire. However, the book also raises issues dealing with metaphysics and social/political philosophy. In the story, Leonardo deals with the inability to scare someone, and in a society of monsters, Leonardo finds himself socially confused–he just doesn’t have the “know-how’ to instill fear into others. This raises the question as to why Leonardo lacks the ability to preform like the rest of his society and what the possible outcomes of not fitting in could be.

Metaphysics is brought into the story of Leonardo by having him change his goals midway through the story. He decides not to scare people, and in doing so, it could be said that he is stripped of what makes him a monster. This prompts the children to discuss the characteristics of being a monster, the loss of essential qualities, and if it is possible to lose what it means to be monster altogether. By doing this, the children could be left discussing what are and are not the key characteristics of being and come to a greater understanding of what it is to be something.

In addition, the topic of social and political philosophy is raised in Leonardo the Terrible Monster with the interactions between Leonardo and his society of monsters. Leonardo is singled out as being the only Monster unable to frighten people, and he is thereby forced to make the decision about his status in society. Initially, he attempts to simply make himself scary, changing his tactics and methods to fit in with his society. This fails and Leonardo is left feeling outcast. This is another situation children should be able to relate to–feeling alone. With this in mind, children should be able to discuss what it means to fit into a crowd. What’s more, in the story Leonardo is able to realize that he does not require the acceptance of his peers, and children will be able to discuss if the need for fitting into society is truly necessary to attain happiness, or if happiness is acquired by acceptance of individuality.

Regarding philosophy of mind, you might introduce the topic of fear. Fear is something everyone can relate to, but it is doubtful that children would have debated the actual existence of fear, i.e. what makes something scary to one person and not others? Throughout the story, fear is dealt with in a very comical sense using monsters with 1,642 teeth and other weird things. Since Leonardo is the only monster who lacks the ability to frighten anyone, it allows children to discuss what is and is not integral to being scary. This ideally allows them to consider all aspects of fear. It is to be hoped that by the end of the discussion, the children will be able to come to a conclusion about the very nature of fear–determining and understanding that fear cannot be universal to everyone and that fear in itself is an individual experience.

Furthermore, philosophy of mind can again be brought into the conversation with discussion about the nature of responsibility and desire. After Leonardo realizes he is unable to fit in with his peers, he is forced to consider his responsibility as a monster and his desire to have a friend. This topic relates to children and the responsibilities they have by getting them to discuss what a monster would feel he “must” do and how it could be acceptable for him to attain happiness even if he did not fulfill his responsibilities as a monster. In addition, children should be able to discuss instances when their responsibilities did not match what they truly desired to do and then be able to discuss which one is more important. With luck, children will be able to come to the understanding that responsibilities are not “set in stone,” and they do not always trump the desires of an individual.

Questions for Philosophical Discussion

Before Reading

  1. What face do you make when you are scared?
  2. What are you afraid of? Why are you afraid of these things?
  3. What makes these things scary?

During Reading

  1. How would you feel if you learned you weren’t scary?
  2. What would you do to scare someone?
  3. Why does Leonardo want to scare Sam?
  4. Should Leonardo want to scare Sam?

Responsibility and Desire

  1. What are some things you are supposed to do?
  2. What are things you want to do?
  3. What is the difference between the two? Which is more important?
  4. Is it wrong to do something you want to do rather than something you’re supposed to do? What makes it wrong?


  1. Have you ever scared anyone? Would you ever intentionally scare someone?
  2. Can being scared be a good thing?
  3. Was Sam afraid of the things he was talking about?
  4. Are people afraid of different things? If so, why?
  5. Can everyone be afraid of the same thing? Why or why not?


  1. Why did Leonardo want to scare people so badly?
  2. Have you ever felt like you didn’t fit in? Why?
  3. Why does Leonardo decide to be friends with Sam?
  4. How did Leonardo feel after he became friends with Sam?
  5. Did Leonardo ever really need to fit in with the other monsters?


  1. Is Leonardo a monster?
  2. What makes a monster a monster?
  3. Does Leonardo fit the description of a monster?
  4. Is he still a monster if he doesn’t fit the description? Why or why not?
  5. (Depending on the response from the children) When does Leonardo stop being a monster? What changed about him?

Original questions and guidelines for philosophical discussion by Nicholas Juselius and Jarmila Lilly. Edited June 2020 by The Janet Prindle Institute for Ethics.

Find tips for leading a philosophical discussion on our Resources page.

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Back to All Books Illustrated book cover for Leonardo the Terrible depicting the top half of a monster's face. He has a round head with fuzzy brown fur, turquoise eyes, and two small horns. He looks worried. Download & Print Email Book Module

About the Prindle Institute

As one of the largest collegiate ethics institutes in the country, the Prindle Institute for Ethics’ uniquely robust national outreach mission serves DePauw students, faculty and staff; academics and scholars throughout the United States and in the international community; life-long learners; and the Greencastle community in a variety of ways. In 2019, the Prindle Institute partrnered with Thomas Wartenberg and became the digital home of his Teaching Children Philosophy discussion guides.

Further Resources

Some of the books on this site may contain characterizations or illustrations that are culturally insensitive or inaccurate. We encourage educators to visit the Association for Library Service to Children’s resource guide for talking to children about issues of race and culture in literature. They also have a guide for navigating tough conversations.  PBS Kids’ set of resources for talking to young children about race and racism might also be useful for educators.

Philosophy often deals with big questions like the existence of a higher power or death. Find tips for leading a philosophical discussion on our resources page.

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