Norwood by Charles Portis (1966). The comic conversation and surreal adventure that distinguish Portis’s fiction shine in this first novel about Norwood Pratt, a war hero with country music dreams who’s stuck in a small Texas town. Seeking escape, Norwood decides to find an old Marine buddy who owes him seventy dollars.
Notes from the Underground by Fyodor Dostoevsky (1864). Aloof, unhappy, and tortured by his own “hyperconsciousness,” Dostoevsky’s narrator prefers to remain underground, away from normal life, because at least there he can be free.
Oedipus trilogy by Sophocles (496–406 b.c.e.). Like an existential sadist, Sophocles explores the tragic complexities of fate by hurling his characters into situations in which they are simultaneously guilty and innocent, forced to choose between right and right or wrong and wrong—or some painfully imprecise combination of the two.
Of a Fire on the Moon by Norman Mailer (1971). For many, the moon landing was the defining event of the twentieth century. So it seems only fitting that Norman Mailer—the literary provocateur who altered the landscape of American nonfiction—wrote the most wide-ranging, far-seeing chronicle of the Apollo 11 mission.
Oldest Living Confederate Widow Tells All by Allan Gurganus (1989). Smart, funny, sharp-tongued Lucy Marsden was seventeen when she married a fifty-year-old veteran of the Civil War, Captain William Marsden.
Olive Kitteridge by Elizabeth Strout (2008). Carolyn Leavitt writes: “Prickly Maine denizen Olive Kittridge presides over these stories, and she’s as awful as she is appealing. The novel unspools thirty years of relationships, illuminating small town life in Maine and the pain, panic and yearning of its people.
On the Road by Jack Kerouac (1957). The ur-novel of the Beat generation, Kerouac mythologizes an America that is always just over the next hill or waiting in the next bar, the next town, the next bottle, or a lover’s bed, and “the mad ones” who chase such visions.
One Day in the Life of Ivan Denisovich by Alexander Solzhenitsyn (1962). The author draws on the eight years he spent in Soviet prisons to write this harrowing novel of the Soviet gulags. Inmates and prisoners are always cold, always hungry, always scheming for crumbs, and willing to betray each other for less in this Siberian labor camp.