Old School takes place in 1960, as time drew a leisured breath before the rapid sprint of The Sixties began. The story is set in a boys’ prep school in a wooded arcadia a long train ride north of New York City.

“I pictured the black-beamed dining hall loud with voices. The chapel windows blazing red on winter afternoons. The comradely sound of the glee club practicing, the scrape of skates on the outdoor rink, a certain chair in the library, the deep peace of the library. . .” The voice is that of the nameless narrator, a scholarship boy from the Pacific Northwest who finds himself adrift in the chilly waters of WASP privilege.

As today’s reader knows, in just a few years that world of certainties would fracture, and though the old order would eventually knit itself back together again, the iron imperatives of class would not be quite the same again. But the assassin’s shot had not yet rung out. Socialites had not yet hosted Black Panthers at radically chic gatherings, and the children of privilege had not traded their Brooks Brothers duds for velvet rags. The protagonist must come of age in a world of rules no less binding for being unarticulated. “Class was a fact. Not just the clothes a boy wore, but how he wore them. How he spent his summers. The sports he knew how to play. His way of turning cold at the mention of money, or at the spectacle of ambition too nakedly revealed. You felt it as a depth of ease in certain boys, their innate, affable assurance that they would not have to struggle for a place in the world.”

But the school has its routes to earned success as well. All the boys worship at the shrine of literature in a way that would be unthinkable today (but that I can attest, having come along a scant five years later, was a reality in some circles at the time). The whole school is mad about writing and writers and all the boys are dying to excel in the literary contests held periodically by the school. In their dorm rooms the boys toil away into the wee hours at poems and short stories. Drawing on their connections, the headmaster and teachers invite leading lights in the field of letters to campus to address the student body – and to meet with the boy who submits the winning entry to writing contests judged by the authors themselves. Some of the funniest scenes in the book describe the visits of Ayn Rand and Robert Frost to the school and their peculiar egotistic responses to the boys’ literary efforts.

Like his fellows and like adolescents everywhere, the protagonist desires both to conceal his inner self and to reveal himself in a burst of authenticity. In this charged state, he enters upon a quest to write something that will demonstrate his superiority and win him an audience with the most thrilling celebrity author of all: Ernest Hemingway. The plot turns on his ambition and the lengths it drives him to. As the headmaster of the school says when introducing Frost to the student body: “Make no mistake. . . a true piece of writing is a dangerous thing. It can change your life.”

The title Old School, both ironically reverent and dismissive toward the citadels of WASP culture, expresses the deep duality in the book. Like Fitzgerald’s Midwestern dreamers before him, Wolff’s narrator is more than half in love with gothic chapels and the fine green lace of New England woods edging into spring. But the longest shadow the book casts is into the future – into the protagonist’s tour as a soldier in Vietnam, into years of work transforming himself into a writer, into a reconfigured totally unexpected world. The most compelling aspect of this complex successful novel is its artful positioning at a turning point in time, when for a moment the Old School still reigned.