Seize the Day By Saul Bellow

“Everyone was supposed to have money”—at least that’s how it seems to Tommy Wilhelm, the divorced, unemployed salesman in Bellow’s fevered story of ambition and regret. Living in an Upper West Side hotel with his father (who pesters Tommy to find a job where he’ll make “five figures”), Tommy has given his entire savings to a possible con man, and over a single, frenetic day, must hustle to avert disaster. Overheated and desperate, by turns despairing and determined, Tommy is one of Bellow’s most affecting characters, a powerful refutation of the myth of the self-made American. As Bellow writes: “You can spend the entire second half of your life recovering from the mistakes of the first half.”

Disgrace By J.M. Coetzee

On its icy surface, this Booker Prize winner is the story of English Professor David Lurie, who is fired for coldly seducing a young female student. Shunned by his colleagues, humiliated in the press, Lurie flees to his daughter’s house in the country to confront harsh post-apartheid realities that mirror his own dark nature. In Coetzee’s spare, crystalline prose, Disgrace is a sharp allegory of South Africa’s shameful history and wrenching reconciliation. Unmoored by the loss of everything he once valued, Lurie is singularly compelling and detached, eager to accept his fate but unwilling to consider culpability: “Confessions, apologies: Why this thirst for abasement?” By the end, Coetzee somehow finds in Lurie’s quiet drift toward redemption a question of great suspense. “A good person,” Lurie muses late in the book. “Not a bad resolution to make, in dark times.”

The Ax By Donald E. Westlake

After 25 years with the same paper company, Burke Devore lost his job following a merger. Two years later, he’s still looking for work and on the verge of desperation when the perfect position opens in New York. But 52-year-old middle managers aren’t especially sought-after, and so, in this dark and comic revenge fantasy, Devore decides to murder the other potential job candidates. Westlake’s straightedge humor keeps the unlikely plot running and a healthy dose of the mystery genre’s requisite plot twists and surprises keep the pages turning; the result is kind of like The Office meets Dexter. Westlake, the prolific author who died in 2008, wrote crisp, unassuming prose and reveals a CEO’s knack for streamlined efficiency himself by combining his protagonist and antagonist into a single position.

Factotum By Charles Bukowski

This is the second and the best of the autobiographical novels featuring Bukowski’s boozy alter ego Harry Chinanski, whose “ambition is handicapped by laziness.” Near the end of World War II, the 4F Harry stumbles around the country, sleeping with women almost as downtrodden as he, and taking and losing a string of truly awful jobs—jackhammering ice, putting brake shoes in boxes, dusting off statues... Each job is a small battle of wills pitting Harry against a different boss, with Harry’s irrepressible will to get drunk and do as little as possible always prevailing. Told in compact bursts of simple prose, Factotum reveals Bukowksi as a kind of poet laureate of deadpan debauchery. “I always started a job with the feeling that I’d soon quit or be fired, and this gave me a relaxed manner that was mistaken for intelligence or some secret power.”

Mailman By J. Robert Lennon

Mailman is not a superhero but an actual postal carrier—and a particularly creepy one—in this, Lennon’s wonderfully neurotic black comedy. Robbed of an academic career 30 years earlier when, excited about a discovery, he fell forward and accidentally bit the eyeball of a professor, Albert Lippincott is now a committed mail carrier who not only delivers letters in his sad-sack college town, but often reads and answers them. Apparently, this is frowned upon because when his supervisors catch wind of it, there’s an inquiry straight out of Kafka, and Mailman loses the one thing that has given his life meaning: his job. Wondering how he’ll “fill the hours” of the rest of his life, he looks to his family, the root of his twisted self. In this surprisingly poignant portrayal of obsession, the most harrowing scene, for anyone who’s ever looked for work, is when Mailman, poring over the want ads at his father’s retirement community, realizes he’s been looking for jobs in a two-year-old newspaper.

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Jess Walter is the author of five novels—including The Financial Lives of the Poets, which was just released in paperback, and The Zero, a 2006 National Book Award finalist—and one nonfiction book. His essays, short fiction, criticism, and journalism have been published in Details, Playboy, Newsweek, The Washington Post, The Los Angeles Times, and the Boston Globe.