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Philip Roth’s legacy of acclaim and notoriety, explained in 5 novels

The Pulitzer-winning novelist’s vital, vibrant career spanned decades. Here’s where to start.

Philip Roth, the prolific and influential writer, died Tuesday of congestive heart failure. And though the death of an 85-year-old man is rarely greeted with shock, it’s still hard to imagine a world without Roth.

Even in retirement, which he began in 2010 after a last act that found him turning out books at an astounding pace, Roth made his presence felt, emerging for the occasional interview to comment on the state of the world from the perspective of a New York retiree who spent his days reading books and watching old movies. (Roth on President Donald Trump, speaking to the New York Times in January of this year: “a massive fraud, the evil sum of his deficiencies, devoid of everything but the hollow ideology of a megalomaniac.”)

The obituaries running today include such words as “giant” and “lion,” but even these seem insufficient. Born in Newark in 1933, a time and place whose influence would be felt throughout his body of work, Roth embarked on a writing career after spending time at Bucknell University, the University of Chicago, and a brief stint in the Army that ended when he sustained a back injury during basic training.

He published his first collection of stories, Goodbye, Columbus, in 1959, winning the National Book Award the following year and establishing a reputation for controversy by addressing themes of Jewish identity and cultural assimilation, occasionally in less than polite terms. It was a preview of things to come.

The acclaim, controversy, and notoriety Roth achieved via that early breakthrough paled to what greeted him with the publication of the 1969 novel Portnoy’s Complaint, a book whose dark humor and sexual frankness helped blow the doors off what was possible in American literature at the end of a decade that saw many of the old rules falling away. Even its cover, by graphic artist Paul Bacon — the title and author’s name in a big, stylized font against a searing yellow background — instantly evokes the era.

But Portnoy’s Complaint was just the beginning of a new phase in Roth’s career, which would find him producing vital, vibrant work for decades to come. With a writer as prolific as Roth, it’s difficult to know where to start, so here are five possibilities (presented with the acknowledgment that five different choices might have worked equally well).

Portnoy’s Complaint (1969)

For his most famous novel, Roth chose the form of a long monologue delivered to a psychoanalyst. This not only allowed him to end the book with a devastatingly funny punchline but created a context that makes sense of the rawness of protagonist Alexander Portnoy’s rambling reflections on being young, horny, Jewish, and in thrall to an overbearing mother. Portnoy spiels, and sometimes shouts, about his childhood, his desires, and the conflict between his need to be a “good boy” and the urges that make that seem impossible.

The book’s frankness, particularly its detailed and voluminous descriptions of masturbation, made it instantly notorious. (Roth makes it hard to look at liver the same way ever again.) Its humor and insight confirmed him as a major writer, but it’s not, in many respects, representative of the writer he’d become. It’s a cry from the id that, once expelled, allowed for subtler explorations of some of the same themes in later work.

The Ghost Writer (1979) and American Pastoral (1997)

At the end of the 1970s, Roth introduced the recurring character Nathan Zuckerman, who’d serve as a frequent alter ego until Roth laid him to rest with Exit Ghost in 2007. In his first appearance in The Ghost Writer, Zuckerman is a young writer still finding his voice and excited to spend the night at the home of the famous author E.I. Lonoff.

But Lonoff’s home, Zuckerman discovers, is not a peaceful one, and his insights into human nature, however profound, have done little to help him find happiness or to avoid an unhappy marriage. Just as confusing to Zuckerman: the presence of Lonoff’s assistant, a young woman named Amy whose mysterious origins prompt Zuckerman to imagine she’s really Anne Frank, having survived the Holocaust and taken to living anonymously in America under an assumed name. It’s a daring device that allows Roth to explore the meaning of Frank’s life and the role of literature while reflecting on his own career.

Zuckerman wouldn’t be Roth’s only alter ego, a group whose number occasionally included a character named “Philip Roth.” But he’s the one Roth would return to most frequently, whether chronicling his own adventures in the literary world — 1981’s Zuckerman Unbound uses Zuckerman to revisit the Portnoy’s Complaint phenomenon — or using him as a melancholy narrator in later novels like American Pastoral.

In Roth’s Pulitzer Prize-winning 1997 novel, Zuckerman’s attempts to compose a speech for a high school reunion leads him to nothing less than an elegy for lost youth and a whole generation’s unrealized ambitions:

Am I wrong to think that we delighted in living there? No delusions are more familiar than those inspired in the elderly by nostalgia, but am I complete mistaken to think that living as well-born children in Renaissance Florence could not have held a candle to growing up within aromatic range of Tabachnik’s pickle barrels? Am I mistaken to think that even back then, in the vivid present, the fullness of life stirred out emotions to an extraordinary extent?

As with Portnoy, Zuckerman allowed Roth to use the particular experiences of one character to explore universal concerns. We all have our equivalent of Tabachnik’s pickle barrels and a youthful Eden to which we can never return, and that realization sets the tone for a story of a different sort of lost paradise that plays out against the background of the turbulent 1960s.

The Plot Against America (2004)

When published, The Plot Against America seemed like a departure for Roth, an excursion into an alternate history that imagined what would happen if fascists, led by Charles Lindbergh, came to power in 1940.

Roth explores the possibility in the most personal way possible, by imagining how it might have affected a fictional version of his own family. The conceit both allows him to explore the persistence of anti-Semitism in American culture and, now chillingly, the ways in which America has failed to immunize itself against demagogues and authoritarians.

Everyman (2006)

Roth ended his writing career with a series of tightly focused novels including this slim, powerful volume about an unnamed, thrice-married, thrice-divorced New Jersey-born protagonist. Opening at his grave, Everyman follows him almost back to the cradle as he recalls a life he now views with regret, reflecting on the many years behind him and the short span ahead.

Roth treats his protagonist sympathetically but views him clearly, and the book ends on a consideration of final things that finds Roth striking a typically unsparing note: “He was no more, freed from being, entering into nowhere without even knowing it. Just as he’d feared from the start.” Even looking death in the face, Roth knew it was his responsibility to not turn away.