From Portnoy's Complaint to American Pastoral: Philip Roth's 10 best novels

Goodbye, Columbus (1959)

In his debut, consisting of a novella and five short stories, Philip Roth established two of his most important themes: Jewish-American identity, and sex. Many readers were astonished by the freshness and audacity of the 26-year-old’s prose — with Saul Bellow remarking: “This is not the work of a beginner” — but the book was attacked for its satirical depictions of middle-class Jews.

Portnoy’s Complaint (1969)

This comic masterpiece takes the form of a 272-page monologue. The speaker, Alexander Portnoy, is a young Jewish bachelor — smart, over-mothered, neurotic and chronically aroused. With its feverish tone, and graphic riffs on Portnoy’s boundlessly inventive masturbatory routines, the novel made Roth famous — unable, he later said, to walk down the street without someone yelling: “Hey, Portnoy, put it away!”

The Breast (1972)

One morning, David Kepesh — one of Roth’s many alter egos — wakes to find himself transformed into a 155-pound breast. Drawing on the traditions of Kafka and Gogol, this short work is more a curiosity than anything else, but still fizzes with raucous, surrealist energy.

The Ghost Writer (1979)

Roth spent most of his career teasing readers about the relationship between himself and his creations — was he writing fiction or simply autobiography? Here we are introduced to the longest-running of all his alter-egos — Nathan Zuckerman, a brilliant young writer spending a night at the home of his literary hero, in the company of a woman whom he begins to suspect is Anne Frank.

The Counterlife (1986)

Next to The Counterlife, Roth’s earlier experiments with metafiction seem remarkably tame. Flitting between America, England and Israel, its five parts present variations on the same story — of Zuckerman and his brother, Henry — with a cacophony of conflicting voices. But while offering a radical new approach to literature, it also manages, as Julian Barnes noted, to be “f---ing funny".

Sabbath's Theater (1995)

Roth thought Sabbath’s Theater was his best novel, though it divided even his fans. It’s easy to see why: the exploits of Mickey Sabbath — once a famous puppeteer, now a gleefully lecherous old man — are exuberantly perverse, even by Roth’s standards. But plumbing the depths of his revolting protagonist was, for Roth, an exercise in “freedom” — and “that’s what you’re looking for as a writer”.

American Pastoral (1997)

After his time with Mickey Sabbath, Roth said he wanted to write a novel about a “conventionally virtuous man”. Here, Nathan Zuckerman returns to tell the story of Seymour “Swede” Levov — a handsome, all-American businessman whose life comes crashing down during the cultural upheavals of the Sixties and Seventies. Sweeping and elegiac, its exploration of “the American berserk” has plenty of resonance today.

The Human Stain (2000)

Like American Pastoral, The Human Stain sets a personal crisis against wider historical events. Nathan Zuckerman, in his penultimate outing, tells the tale of his neighbour Coleman Silk, a college professor forced out of his job after accusations of racism, as the Lewinsky scandal simmers in the background.

The Plot Against America (2004)

To keep readers on their toes, Roth also had an alter ego called… Philip Roth. This counter-factual history follows the fortunes of the (fictional) Roth family after Franklin D Roosevelt has been defeated by Charles Lindbergh in the 1940 presidential election.

Everyman (2006)

Roth never shied away from the biggest theme of all. Everyman, a slim but powerful meditation on death, begins at the funeral of its unnamed protagonist, and traces his life — in familiar East Coast surroundings — from his earliest confrontation with mortality.