Old School Study Guide

Tobias Wolff was born to Rosemary and Arthur Wolff in 1945 and was raised Catholic, though later in life he learned that his father had Jewish heritage. His parents separated when Wolff was five years old and his elder brother Geoffrey was 12. Wolff lived with his mother in a variety of places, including Seattle, where she remarried. During this time, his father and brother lived on the East Coast, and Wolff had little contact with them. Wolff attended high school near Seattle and then applied to and was accepted by The Hill School, located outside Philadelphia. However, Wolff forged his transcripts and recommendation letters and was later expelled by the school. He was in the army from 1964 to 1968 and served in the Vietnam War. This experience influenced him to write his 1984 novella The Barracks Thief, which earned the PEN/Faulkner Award for Fiction. After his time in the army, Wolff earned an English degree from the University of Oxford in 1972 and an MA in Creative Writing at Stanford in 1975. Wolff then taught at Syracuse University from 1980 to 1997  and published his first short story collection in 1981, followed by two more in 1985 and 1997. In 1997, Wolff transferred to Stanford University and continues to teach there. Wolff chronicled his early life in This Boy’s Life (1989), In Pharaoh’s Army (1994), and Old School (2003). His most recent short story collection was published in 2008. Wolff received the Rea Award for the Short Story and won the O. Henry Award three times. Wolff is married with three children and currently lives in California.

The novel’s plot takes place from 1960 to 1961, but most of the literature and literary figures referenced in the novel belong to the first half of the 20th century. In the 1910s, many writers wanted to overturn traditional modes of writing; they were motivated by the horrors of World War I, technological advances, and other societal changes in the early 20th century. This gave birth to the modernist movement, in which writers and artists experimented with literary form. Many of the boys in Old School admire and imitate the writers of this movement—particularly Ernest Hemingway, F. Scott Fitzgerald, William Faulkner, Ezra Pound, Gertrude Stein, T. S. Eliot, and e.e. cummings. Many of the boys also look up to writers from the Beat Generation, a 1950s literary movement that focused on spirituality, sexual liberation, and anti-materialism. Jack Kerouac and Allen Ginsberg are two of the Beat authors referenced in Old School.

Old School references many works by the three visiting writers featured in the novel, primarily Robert Frost (“After Apple-Picking,” “Mending Wall,” and “Stopping by Woods on a Snowy Evening”); Ayn Rand (The Fountainhead and Atlas Shrugged); and Ernest Hemingway (In Our Time, The Sun Also Rises, and A Farewell to Arms). Other classic literature referenced in the novel includes Allen Ginsberg’s poem “Howl” and the works of William Faulkner (A Light in August) and F. Scott Fitzgerald (The Great Gatsby). The book’s setting at a boy’s prep school also hearkens to coming-of-age novels like J.D. Salinger’s The Catcher in the Rye and John Knowles’s A Separate Peace. Old School is semiautobiographical, and Wolff also wrote two memoirs of his early life: This Boy’s Life and In Pharaoh’s Army.