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Content Warning: This section of the guide includes discussion of bullying.
Gregory’s story is in many ways about the triumph of his authentic self. Aside from his desire for love and companionship, Gregory is drawn to two things as an individual: art and nature. His love for art is communicated by both his actions and the text’s language. Gregory takes art supplies with him wherever he goes: that this is habitual is conveyed early in the story through the repeated use of the phrase “his tablet and paints and brushes” (6, 7, 11). He paints pictures and puts them on the walls of his first-ever bedroom, indicating that what makes it “his” is being adorned with his art.
Significantly, one of these paintings depicts a sunflower, which hints at his love for nature. Gregory’s appreciation for nature is shown in several ways. First, in his initial response to his new home, which he is disappointed to see is surrounded by concrete and is on a street without any trees. Then, when Gregory is upset by Uncle Max, he goes outdoors and feels calmer when he looks up at the sky. Finally, Gregory’s great excitement about Mr. Hiller’s drawings of plants on the school chalkboard comes from the union of his two loves: art and nature.
For much of the story, other people do not offer Gregory much appreciation for this authentic self. Max covers up Gregory’s paintings with car posters. When Gregory tries to share his appreciation for his outdoor refuge—the abandoned chalk factory—his mother tries to get him to choose a less dirty place to play. When Gregory decorates the walls of the burned-out building with his elaborate chalk garden, his peers mock him for it.
Gregory does not let others’ responses deter him, however. He insists that his garden is a “real” garden because it is a reflection of him, and he does not think that the other students’ more literal understanding of what a garden is should limit him. Ironically, Vance accuses Gregory of “bragging” (19, 50)—representing himself inauthentically—when in fact, Gregory is doing his best to be the most authentic version of himself he can be. In the end of the story, Vance and everyone else recognize this. Gregory is, ultimately, richly rewarded for staying true to himself when his parents, Uncle Max, his teachers, and his classmates finally see and appreciate what makes him so special.
One of Gregory’s core characteristics is his optimistic determination not to be defined by his circumstances. Both his home life and his school life are difficult, and he faces constant reversals of fortune. Instead of lashing out or feeling sorry for himself, however, he persists in working to better his situation.
Gregory’s home life is made difficult by his parents’ financial precarity. He has to move into a new home on his ninth birthday because of his father’s job loss. When Gregory sees his tiny new house surrounded by concrete on a street mainly inhabited by businesses and factories, he does not dwell on its disadvantages. Instead, he focuses on how exciting it is to finally have a room of his own, and—despite not having a birthday celebration—declares the day he gets his own room his “best birthday […] ever” (10).
Gregory’s first reversal of fortune is centered on this bedroom. It is only his for one night; the next day, Uncle Max moves into the room. Gregory is upset about losing his refuge, particularly since he does not get along with Uncle Max. He does not let this defeat him, however—he goes outside and finds a new place of his own in the burned-out building behind his house. The abandoned chalk factory is filthy and full of rubble. It is a place that most people would find unappealing, but Gregory immediately sets about cleaning it up and making himself seats from old bricks he finds lying around in the rubble.
Because his parents are stressed and busy, they are not always able to offer Gregory the support he needs during this trying time, such as taking him to school on his first day. Instead of being upset about this, Gregory confidently assures his mother that he can handle getting there and introducing himself on his own. Mother and Daddy are too distracted to come see the chalk factory that has become so special to Gregory, but he keeps trying to interest them and stays connected to them instead of becoming alienated.
Another significant reversal occurs when Gregory gets excited about planting a garden using plants from Mr. Hiller’s nursery. When Gregory learns that growing a garden at his house is impossible, he is initially upset. But then, Gregory turns this disadvantage into an opportunity for something even more special, creating a chalk garden in the abandoned factory. Even when other students from his school intensify their bullying by coming to the burned-out building and mocking his work, Gregory does not crumble. He is deeply hurt, but not discouraged from drawing his cherished chalk garden. Gregory never uses his circumstances as an excuse for self-defeating behavior or a lack of forward progress in his life. He is like the sunflowers he so admires, thriving despite adverse conditions and always turning his face toward the sun.
Gregory’s persistence and optimism are not the only forces responsible for the transformation of his life after he moves into his new home: A large part of his transformation is due to his love of art. Painting and drawing are Gregory’s main hobbies. He takes his art supplies with him wherever he goes, and the first thing he does in his new room is create two new paintings that he can tack to the walls to celebrate finally having a room of his own. Gregory’s art class is the only class specifically described in the narrative, emphasizing how important it is to him.
Art allows Gregory to express himself. He can use it to show his love for nature—as when he paints the sunflower and draws the chalk garden—and his longing for a larger home—as when he draws the castle in art class. His drawings are something he creates from his own imagination and passions, and he can control their details exactly as he chooses. In his small, depressing house where he has to deal with Uncle Max’s domineering and insensitive behavior, and where his parents do not have much time for him, Gregory lacks this kind of power. Art is an important outlet, allowing him to process his ideas and feelings through a creative act instead of through potentially more destructive routes.
The narrative reinforces how much art matters to other characters as well. Ivy is also a great lover of art. She is a shy child whose voice is barely “more than a whisper,” but when she creates art, she is able to “speak” loudly (23). Miss Perry and Miss Cartwright reinforce the importance of art when they buy art supplies for Ivy and make a fuss over her for winning the school’s art competition. Miss Cartwright claims that the entire school is proud of Ivy, making it clear that art is something widely valued at Dover Street School. Even Max makes a statement about the power of art when he uses his car posters to cover up Gregory’s paintings, implicitly saying with this gesture that his self-expression is more important than Gregory’s.
Like Ivy, Gregory has a voice that is not being properly heard. He feels a little neglected at home and isolated at school, as if no one really sees him and values him for who he is. In the end of the story, it is the communicative power of art that finally allows his family and community to “hear” Gregory. After everyone sees his extraordinary chalk garden, his life is transformed: He finally has his parents’ attention, Uncle Max respects him more, and he gains the companionship of friends that he has been craving for so long.



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