Although the prep school plays a small part in it, America's favorite preppy book seems to be J.D. Salinger's timeless classic The Catcher in the Rye. It's one of my favorite novels and I can't recommend it highly enough. When we first meet Holden Caulfield, the books' narrator and hero (sometimes referred to as an anti-hero), he is a student at an elite east coast prep school known as Pency Prep. Holden is the son of a wealthy corporate lawyer, but at the start of the book, he is about to flunk out of school entirely. After arguments with his roommate and another student who he doesn't get along with, Holden escapes to nearby New York City, where he is from, wanting to avoid breaking the news to his parents for a few days. That's just where the story starts. Although it isn't completely about preppy things or people, every preppy bedroom should include a well-loved copy of this book or a brand new one because the one you read at boarding school fell apart.
This Side of Paradise - F. Scott FitzgeraldWe all know the story of the great Jay Gatsby and some of you may have even read Tender is the Night, but so few people seem to be acquainted with Amory Blane, the hero of F. Scott Fitzgerald's most underrated novel. Amory is the classic son of privilege, born into a prominent mid-west family and sent to an elite Connecticut boarding school and later educated at Princeton University (so prep it hurts). That's just beginning, though, as Amory takes off on a journey through life and self-discovery, ending with the iconic phrase "I know myself. But that is all I know" This Side of Paradise is Fitzerald's memoir of sorts, said to have been inspired by events from his own life. One of the most iconic figures of prepdom, Fitzgerald was himself educated at an elite boarding school followed by...you guessed it, Princeton. This is truly the best American novel concerning prepdom. Though the prep school plays a small part, Amory is unquestionably the preppiest character to ever have been born in American literature.
Finally, we come to a novel that takes place entirely at a prep school. Written by John Knowles, a graduate of Phillips Exeter Academy and Yale University, it tells the story of Gene, the lonely, introverted intellectual new kid at the prestigious Devon School, an elite New England boarding school. The first in his family to attend prep school, Gene doesn't quite feel like he belongs, particularly when he meets Finny, his wealthy roommate. Handsome, charming, daring, and athletic, Finny is everything Gene is not, yet he finds him oddly fascinating and as the story unfolds, we learn why, particularly as the boys discover why that they both need each other while Gene harbors a guilty secret. Meanwhile, as their country hovers on the brink of WWII, the boys of Devon face decisions that will affect them not just at school, but in the world beyond. It all leads up to an emotional climax that no one could have predicted.
The Rector of Justin - Louis AuchinclossFirst published in 1964, this quintessential prep school novel spent over 8 months on the bestseller list. Contrary to what the book's cover (left) might suggest, it is actually not the story of a scared little boy who enters prep school for the first time. Moreover, it tells the story of Dr. Francis Prescott, the founder and head of an all boys Episcopal prep school, located in New England. It is told from the point of view of many people who knew him. While some loved him, some couldn't stand the man and others feared him. Told by a group of interesting and varied voices, it covers the extraordinary man's journey over the course of his whole life, from his boyhood to beyond his death. The author, the renowned Louis Auchincloss was an alum of the prestigious Groton School in Groton Massachusetts and Yale University as well as the University of Virginia Law School. His prep school background is certainly reflected in his writing.
Now for a look at a book that examines the prep school life in a slightly different way. New Boy is the story of Rob Garret a young man who leaves his home in Virginia to become the first African-American student at Draper, an elite Connecticut boarding school. It is based on author Julian Houston's own experiences at the elite Hotchkiss School in Lakeville Connecticut. Rob studies hard and boldly refuses to stereotype himself. Although he himself encounters little racism, he is shocked when one of his friends is brutally bullied for his ethnicity. Even more surprising to him is the fact that the school refuses to do anything about it or cross the offending students, who are very well connected. Meanwhile. the civil rights movement is taking shape back in Rob's home territory of the South, which will present new challenges as the story takes shape. Houston does a superb job representing the crosscurrents of the civil rights movement through his writing.
Prep - Curtis Sittenfeld
Another prep school alum pays tribute to her academy days in literary form in Prep. In her novel, which offers a semester by semester tour of the elite Ault School, a fictional Massachusetts boarding school, Curtis Sittenfeld drew heavily on her days at the Groton School. Such a story may sound familiar, as it is similar enough to that of John Knowles, who's experiences at Phillips Exeter Academy inspired his quintessential prep school novel A Separate Peace. Although Prep lacks the "poetic angst" that Knowles wrote so well, her heroin Lee Fiora is similar enough to Gene, the hero of A Separate Peace. Like Gene, she is an introverted adolescent who does not come from a family as wealthy as many of her classmates. Much of the story consists of Lee's observations of the world of privilege around her, giving us an honest glimpse of what it is really like to be a scholarship student at a super-elite prep school. Ault isn't quite as she imaged it would be, which goes to show us that maybe the prep school world of khakis and navy blue blazers isn't quite as we tend to imagine it either.
Honorable Mentions -
The Keeper of Dawn - J.B. Hickman
Old School - Tobias Wolff (alum of The Hill School)
Gossip of the Starlings - Nina de Gramont
The Year of the Gadfly - Jennifer Miller
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