Top 10 books about boarding school

From Evelyn Waugh to Molesworth, novels set in these places of privilege are microcosmic studies of oppression and rebellion

Boarding school stories for children make up an entire genre, and have their lifelong devotees – but as in, say, the work of PG Wodehouse, the environment of these books is largely consequence-free. Whatever happens, the slate can usually be wiped clean at the end for the next caper.

In reality, they are places freighted with consequence, and stories for adults set within their walls, such as Lindsay Anderson’s masterful 1968 film If .…, hold an enduring fascination for their microcosmic studies of oppression and rebellion.

My new novel, English Monsters, is about a group of friends who meet at a boarding preparatory school at the age of 10, and whose experiences there resound inescapably in their lives over the next 30 years. So, no Jennings, Bunter or Malory Towers here. Hogwarts is out, too. Everyone at boarding school craves superpowers, because it’s the most obvious response to the powerlessness. But you don’t have them.

1. The Time of the Hero by Mario Vargas Llosa
The novel’s original Spanish title translates as The City and the Dogs, the “dogs” being cadets at a vicious military school in Lima, Peru, based on the Leoncio Prado military academy to which Vargas Llosa was sent at 14. The plot hinges on the theft of an exam paper and subsequent death of the boy who told on the perpetrators. Officials at Leoncio Prado were so outraged by its portrayal in the novel that they held a book-burning ceremony, proving that Britain doesn’t have a monopoly on the association of residential education with deranged nationalistic fervour.

2. Never Let Me Go by Kazuo Ishiguro
One of Ishiguro’s great gifts is to take a very specific context, loaded with constraints, and extract from it a voice and a story that become powerfully universal. Here, the backdrop is Hailsham, a boarding school in the English countryside, where, it emerges, the pupils are clones created for the purpose of having their organs harvested. As the novel progresses, its surface calmness and simplicity are increasingly at odds with a mounting and devastating sense of loss as the novel evolves into a meditation on life’s compromises and squandered opportunities.

Keira Knightley in the 2010 film of Never Let Me Go.
A meditation on life’s compromises ... Keira Knightley in the 2010 film of Never Let Me Go. Photograph: Allstar/Fox Searchlight

3. Frost in May by Antonia White
Nanda Grey is sent to the Convent of the Five Wounds at the behest of her adored father, a recent convert to Catholicism. Girls as young as 11 are told here that they must “live constantly in the spiritual presence of death”, so they “mortify” themselves by putting salt on their pudding instead of sugar, and affixing burrs to the inside of their uniforms. Even when Nanda’s behaviour is exemplary, she is still admonished for lacking “normal, healthy, natural naughtiness”. It’s a booby-trapped environment of Exemptions and Permissions, where you can burn in hell for ever just for eating a found sweet on your way to communion.

4. Decline and Fall by Evelyn Waugh
Sent down from Scone College, Oxford for indecent behaviour after his trousers are stolen by a drunken member of the Bollinger Club, Paul Pennyfeather is exiled to teach at a purgatorial boarding school in Wales. On sports day, the hurdles have been burned for firewood and are replaced by five-foot-high spiked railings, and the starting pistol is Philbrick the butler’s service revolver, which ends up being discharged into the heel of Lady Circumference’s son, Lord Tangent. Among its many delights is the novel’s acknowledgement of the fact that teachers at boarding school often seem as perplexed as the pupils as to how they came to be in such a place.

5. Old School by Tobias Wolff
The novel opens in November 1960 after John F Kennedy has beaten Richard Nixon to the US presidency. The boys at the elite school where this novel is set all favour JFK, partly because “he had his clothes under control” and “his wife was a fox” – but mainly because he “read and wrote books”. The highlight of every term is a visit from a Great Writer, and in our unnamed protagonist’s final year, the visiting writers are Robert Frost, Ayn Rand and Ernest Hemingway, the last of whom will judge a creative writing competition. This sends the pupils into a competitive frenzy and tests the school’s hardwired codes of honour to breaking point.

6. The Ruined Boys by Roy Fuller
Gerald Bracher arrives at boarding school from South Africa after his parents’ divorce. He is desperate to conform and awash with guilt at his own perceived role in their split, attaching himself worshipfully to the headmaster as a replacement father figure. The novel chronicles Gerald’s transformation from eager admirer to rebellious cynic as the school’s (and, by extension, society’s) shortcomings become apparent. The novel is insightful and funny about boarding-school philosophy, as in the scene where Gerald is nervous about the fact that a boxing match is to be held and declares his fear that people might be murdered. “Possibly,” replies his interlocutor. “But they’ll be murdered in a fair way.”

7. Skippy Dies by Paul Murray
The title isn’t a spoiler: Daniel “Skippy” Juster expires within the first few pages of this novel, in the middle of a doughnut-eating race against his friend Ruprecht Van Doren. Skippy’s final act is to burst a doughnut in his fist and paint the words TELL LORI on the floor in jam. This is the jumping-off point for a riotous and digressive tale, both comic and tragic, that relates the experiences of Ruprecht and Skippy at Dublin’s Seabrook College for Boys.

8. Prep by Curtis Sittenfeld
At 14, Lee Fiora becomes fascinated with boarding schools while researching the subject at her local public library. She falls for the handsome boys in the prospectuses she sends away for and ends up, to the mystification of her parents, on a scholarship to the prestigious Ault school in Massachusetts. The environment here is as preppy as it gets – the characters have names such as Cross Sugarman and Gates Medkowski – but the stew of adolescent fears and desires the novel depicts is universal.

A 1954 illustration from Molesworth.
The curse of St Custard’s ... a 1954 illustration from Molesworth. Illustration: Ronald Searle

9. The Compleet Molesworth by Geoffrey Willans and Ronald Searle
I’m not breaking my own rule because the four books collected here are absolutely written for adults, however much they may also appeal to children. They document the exploits and philosophy of Nigel Molesworth, “the curse of St Custards”, his “grate frend” Peason, the “uterly wet” Fotherington-Tomas and a host of other perfectly observed pupils and masters. Many of the jokes can be enjoyed by people of any age, but, for adult readers, the books also read as a cutting social satire of 1950s England.

10. Such, Such Were the Joys by George Orwell
Strictly speaking, this is an essay rather than a book, but it is published as a standalone pamphlet and its gimlet-eyed Orwellian concision make it worth more than many longer tomes on the subject. It describes Orwell’s experiences as a pupil at St Cyprian’s in Sussex before and during the first world war, and wasn’t published until two years after his death because of its incendiary attack on the school, the headmaster “Sambo” and his wife “Flip”.

James Scudamore

The GuardianTramp

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