American author Philip Roth, one of the largest literary figures of the 20th century, died due to heart failure on Tuesday, aged 85. His career spanned 50 years, 30 books, three PEN/Faulkners, two National Book Awards, and one Pulitzer. Usually set in his birthplace New Jersey, Roth’s fiction was known for its autobiographical nature, its blurring of boundaries between fictionality and fact, and the understanding of Jewish American identity, especially masculinity.

“Mr. Roth was the last of the great white males: the triumvirate of writers—Saul Bellow and John Updike were the others—who towered over American letters in the second half of the 20th century," wrote Charles McGrath for The New York Times. In 2005, he became only the third living writer to have his books enshrined at the Library of America, he added.

Lounge pays tribute to his literary life in books.

The debut

Goodbye, Columbus (1959)

While Roth’s work first appeared in print in the Chicago Review, his first published book—the 1959 novella and short-story collection Goodbye, Columbus—was the result of a Houghton Mifflin Fellowship. The novella won him his first National Book Award in 1960 and sold more than 12,000 copies in hardback. The title story first appeared in the Paris Review—and the collection in its entirety deals with the lives and struggles of second and third generation American Jews.

The “apprentice work"

Letting Go (1962)

His debut novel—Roth would later refer to his first two novels as “apprentice work"—Letting Go was written during the years he was married to Maggie Michaelson, and was self-proclaimed to be a serious “literary" exploration of their toxic relationship. Divided into seven sections, the work is derived from Saul Bellow and Henry James.

The best-known

Portnoy’s Complaint (1969)

In a career which spanned over five decades, Roth was a bestselling author only once: his most famous work, Portnoy’s Complaint, sold 420,000 copies in the first 10 weeks after publication. A first-person narrative about Alexander Portnoy, a young Jewish New Yorker who wanted to “put the id back in yid", the book is notorious for featuring the maximum number of masturbation scenes per page. For Roth, it was intentionally rebellious, and “an experiment in verbal exuberance".

The “most un-Rothian"

When She Was Good (1967)

The second in his set of “apprentice work", When She Was Good, which followed his debut by five years, was published in 1967. Named as “the most un-Rothian" of his books by Charles McGrath at The New York Times, it reads as a “Theodore Dreiser- or Sherwood Anderson-like story set in the WASP Midwest in the 1940s". It’s also Roth’s only novel that features a female protagonist: Lucy Nelson.

The auto-fiction

Zuckerman books (1979-2007)

Roth’s autobiographical phase began in 1974 with My Life as a Man, and continued with what’s collectively known as Zuckerman Bound: comprising The Ghost Writer (1979), Zuckerman Unbound (1981), The Anatomy Lesson (1983), and The Prague Orgy (1985). These books feature Nathan Zuckerman, a character widely read as Roth’s fictional alter ego, and overall the books explore authorial vocation and the writing process. Zuckerman later reappears in The Counterlife (1986), where he seems to die of a heart attack and is resurrected afterwards. Books such as Roth’s “confessional novel" Operation Shylock (1993) also stage his auto-fictional tendencies and the character Zuckerman also seeps into his later autobiographical works including The Facts: A Novelist’s Autobiography (1998).

The “American trilogy"

American Pastoral (1997); I Married a Communist (1998); and The Human Stain (2000)

It’s no exaggeration that Roth’s American trilogy defined his career in literary prizes. The first, American Pastoral (1997)—which explored the consequences of the 1960s on a New Jersey family—won him the Pulitzer Prize for Fiction that year. And the final, The Human Stain, won him his second PEN/Faulkner Award. It was also developed into a film in 2003—and starring Anthony Hopkins and Nicole Kidman. The exceptional trilogy, tragic-comic in style and heavily historical in content, saw Roth engage with American politics and concerns for the first time in two decades, and impressively, at age 60.

The later years

Everyman (2006) to Nemesis (2010)

Following the death of several friends and contemporaries (including Saul Bellow in 2005), Roth wrote a sequence of short fictions—focusing on old age and physical deterioration—the first of which was Everyman (2006) which won him his third PEN/Faulkner Award. The novel opens in a graveyard, but it’s his next, Indignation (2008), which is a ghost story in good measure. Roth followed it with The Humbling, which came out the following year, and closed the curtains on this series of shorts—and his career—with Nemesis, about the 50s polio epidemic—in 2010. In the later years, his prose was reportedly bleaker and sparer: some would even say less “literary".

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