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Repton School

From 1929, when he was 13, Dahl attended Repton School in Derbyshire. Dahl disliked the hazing and described an environment of ritual cruelty and status domination, with younger boys having to act as personal servants for older boys, frequently subject to terrible beatings. His biographer Donald Sturrock described these violent experiences in Dahl's early life. Dahl expresses some of these darker experiences in his writings, which is also marked by his hatred of cruelty and corporal punishment.

According to Dahl's autobiography, Boy: Tales of Childhood, a friend named Michael was viciously caned by headmaster Geoffrey Fisher. Writing in that same book, Dahl reflected: "All through my school life I was appalled by the fact that masters and senior boys were allowed literally to wound other boys, and sometimes quite severely... I couldn't get over it. I never have got over it." Fisher was later appointed Archbishop of Canterbury, and he crowned Queen Elizabeth II in 1953. However, according to Dahl's biographer Jeremy Treglown, the caning took place in May 1933, a year after Fisher had left Repton; the headmaster was in fact J. T. Christie, Fisher's successor as headmaster. Dahl said the incident caused him to "have doubts about religion and even about God". He viewed the brutality of the caning as being the result of the headmaster's enmity towards children, an attitude Dahl would later attribute to the Grand High Witch in his dark fantasy The Witches, with the novel's main antagonist exclaiming that "children are rrreee-volting!".

Dahl was never seen as a particularly talented writer in his school years, with one of his English teachers writing in his school report, "I have never met anybody who so persistently writes words meaning the exact opposite of what is intended." He was exceptionally tall, reaching 6 feet 6 inches (1.98 m) in adult life. Dahl played sports including cricket, football and golf, and was made captain of the squash team. As well as having a passion for literature, he developed an interest in photography and often carried a camera with him.

During his years at Repton, the Cadbury chocolate company occasionally sent boxes of new chocolates to the school to be tested by the pupils. Dahl dreamt of inventing a new chocolate bar that would win the praise of Mr Cadbury himself; this inspired him in writing his third children's book, Charlie and the Chocolate Factory, and to refer to chocolate in other children's books.

Throughout his childhood and adolescent years, Dahl spent most of his summer holidays with his mother's family in Norway. He wrote about many happy memories from those visits in Boy: Tales of Childhood, such as when he replaced the tobacco in his half-sister's fiancé's pipe with goat droppings. He noted only one unhappy memory of his holidays in Norway: at around the age of eight, he had to have his adenoids removed by a doctor. His childhood and first job selling kerosene in Midsomer Norton and surrounding villages in Somerset are subjects in Boy: Tales of Childhood.