Roald Dahl ("Boy")
Roald Dahl, nicknamed "Boy," is the author and protagonist of the novel. The child of Norwegian immigrants living in Wales and England, Dahl is viewed by the authorities as a troublemaker at the schools he attends. Although his father considers English schools to be the best in the world, Dahl lives in constant fear of being disciplined with vicious canings from school officials. Instead of continuing with education by going to university, Dahl takes a job at Shell Oil. Later in life, Dahl will become one of the world's most widely read children's authors.
Harald Dahl
The author's father, Harald, is a Norwegian shipbroker who makes a comfortable living for his family after starting a shipbroker company in Wales. In the wake of his daughter's death, Harald falls ill and dies of pneumonia several weeks later.
Sofie Dahl
Dahl's mother, Sofie, is a Norwegian woman who moves to Wales after meeting her husband, Harald. When her daughter and husband die with weeks of each other, Sofie decides to stay in the UK because she hopes to fulfill her husband's wish that his children attend English schools, which he believed to be the best in the world.
Mrs. Pratchett
Mrs. Pratchett is the despicable and grubby owner of the candy shop near Dahl's elementary school. As revenge for her unpleasantness toward him and his friends, Dahl devises a plan to put a dead mouse in her gobstoppers jar. Afterward, she goes to the boys' school and talks the Headmaster into punishing the boys by hitting them with a cane.
Mr. Coombes
Mr. Coombes is the Headmaster of the elementary school Dahl attends as a young boy. He disciplines Dahl and other misbehaving boys with brutal canings.
Matron
The Matron is a nurse responsible for overseeing the boys' health and well-being while they live at boarding school. An imposing, large-chested woman, the Matron strikes fear into Dahl's heart because she is looking for any excuse to send pupils for a caning from the Headmaster. At one point, she confiscates the keys to the tuck boxes, leaving Dahl famished for six weeks.
Captain Hardcastle
Captain Hardcastle is one of the teachers Dahl most fears while at boarding school. He has bright orange hair and an orange mustache that curls up at the ends. When he overhears Dahl ask another boy for a writing nib, Hardcastle accuses him of cheating on his essay and sends him to the Headmaster for a caning.
The Headmaster of Repton Prep School
The Headmaster at Repton is a short clergyman known for the vicious beatings he doles out to boys at the school. Dahl considers it hypocritical that the man preaches mercy and forgiveness in the chapel while carrying on with such brutal punishments. Dahl finds it even more ironic when the man eventually becomes Archbishop of Canterbury, meaning he crowns Queen Elizabeth II in an event half the world watches on TV.
Thwaites
Thwaites is a childhood friend of Roald Dahl. Because Thwaites's father is a doctor, Thwaites impresses his friends with facts purportedly learned from his father. Thwaites eggs on Dahl to prank Mrs. Pratchett with a dead mouse, later accusing Dahl of murder when he suspects Pratchett had a heart attack upon finding the mouse.
Dahl's Elder Sister
Referred to by Dahl as his "ancient" sister, Dahl's eldest sibling is approximately a decade older than Dahl. She is the biological child of Harald and Marie, Harald's first wife, although she is raised most of her life by Dahl's biological mother. She drives the family car into a hedge on the day they receive it, causing an accident that nearly takes Dahl's nose off his face. She also becomes engaged to a young English doctor whom the rest of her family decide to prank after he spoils their summer vacation.
Dahl's Sister's Fiancé
Dahl's sister's fiancé is a young English doctor. He accompanies the family on their summer holiday to Norway. When his presence irritates the family, Dahl stuffs his pipe with goat droppings and the entire family watches eagerly as he coughs and splutters, claiming someone has poisoned him.