Meet William, a devout underachiever. He enters life as the firstborn of identical twin boys. It is the last time he will beat his overachieving brother Clive, or anyone else for that matter, at anything. This is William’s manifesto for the underachiever. It is the chronicle of a lifetime of failure — part diary and part handbook for self-defeat. At once corrosively funny and surprisingly tender, An Underachiever’s Diary is a classic tale of perverse perseverance.

"'Please do not confuse this diary with a memoir written for a therapeutic purpose,' urges William, the narrator of this earnest, tender, achingly autobiographical first novel that reads like a manifesto for Generation Xers. An identical twin born in the mid-1960s to politically liberal parents in Cambridge, Mass., he sets out to define himself through a chronicle of his young life and by everything that his shining-example, more conventional brother is not: an "utter failure," a "screw-up"; in short, an underachiever. Where his brother, Clive, excels (in academics, in making bright friends and winning the heart of the celestial girl-next-door and in getting into Harvard), William becomes infatuated with a kind of grotesque failure — attracting an alcoholic girlfriend, choosing a third-rate college, joining a San Francisco cult. He is the loser son every mother fears having, and he's proud of the ignoble distinction. In carefully and formally constructed, exquisitely cadenced prose, Anastas succeeds in capturing an adolescent's naïveté, self-absorption and instinct for melodrama — and in filtering it all through a fierce intelligence. Cultural signifiers offering a clue to the influences on the narrator are plentiful: William Faulkner, TV shows like A Family Affair, classical authors and St. Augustine. Though William scoffs at being the representative of his maligned generation ("I hear rumors that my condition is widespread"), there are just the right amounts of candor, wit, puerile humor and perverse irreverence in Anastas's work to succeed at that." Publishers Weekly (Copyright Reed Business Information, Inc.)

"[M]ay have been the funniest, most underappreciated book of the 1990s....William's voice is sharp and hilariously scathing; he comes off like a latter-day Holden Caulfield....[A] coming-of-age story that's well worth retelling." Very Short List

"From the first paragraph, Benjamin Anastas has got you." Thomas Mallon

"Recalls Frederick Exley's masterpiece of the genre, A Fan's Notes." New York Times Book Review

"The book's veils of irony are light enough to charm even the coolest reader, and its emotional details, particularly those of William's bond with his faultless brother, ring true." The New Yorker

"Very funny.... A masterpiece of controlled failure in which the narrator fails to deliver on every front." New York Post

"Fantastic.... A fun, funny book." Detroit Free Press

In the mid-1960s, William was the firstborn of identical twin boys. It is the last time in his life he will ever be first in anything.

Benjamin Anastas is the author of The Faithful Narrative of a Pastor's Disappearance. His writing has appeared in The New York Times Magazine, The Paris Review, Men's Vogue, and GQ.