Philip Roth Books, Ranked

Roth finds his voice (or his first great one) through one of postwar lit’s most memorable protagonists. In a long therapy session, “the Raskolnikov of jerking off” unloads all the neuroses and fixations of the hyperarticulate Jew, who seems a stock character today only because Portnoy was such a seminal one.

Roth’s funniest, smartest, most readable experiment in metafiction. When a second Philip Roth turns up in Jerusalem, using the author’s fame to fight anti-Semitism and agitate for the re-dispersal of the Jews, the actual Roth intercedes—and ends up spying for Israel.

Brilliant, smutty, and marvelously nuts, this is the story of an unemployed, priapic puppeteer grieving the loss of his nymphomaniacal, adulterous soulmate Drenka. Notorious for a scene of graveside masturbation (take that, liver!), the book pushes Roth’s obsession with sex and death to its limits. It’s also hilarious.

Arguably Roth’s best novel, certainly his most mature. The Zuckerman book’s real subject is dutiful ex-jock “Swede” Levov, whose family, and entire worldview, falls apart after his radicalized daughter, Merry, bombs their idyllic New Jersey town’s general store.

Roth’s debut is a brisk novella about Neil Klugman, a likable kid from the working-class side of Newark who falls for Brenda Patimkin of tony Short Hills. Roth’s nascent obsessions are evident (sex, class, assimilation), but not yet his trademark voice.

The birth of randy, combative, brilliant Nathan Zuckerman, the vehicle for Roth’s career-long thought experiment about the existential drama of his own career. This quartet (now available in a Library of America edition) takes us halfway through the life cycle of Roth’s success, from the 23-year-old apprentice visiting his reclusive hero (The Ghost Writer) to the mid-thirties celebrity wrestling with his fame (Zuckerman Unbound) to the fortysomething superstar scouring Czechoslovakia for literary talent (The Prague Orgy). Martin Amis has called it, not necessarily negatively, “perhaps the most cramped and stubborn exercise in self-examination known to modern letters.” Runs the gamut of self-absorption, from brilliantly taut to tedious.

The tale of another Newark hero of Zuckerman’s (this time a lefty radio star done in by McCarthy, with help from his ex-wife’s memoir), this sweeping and poignant novel suffered by comparison with American Pastoral (not to mention the gossip over Roth’s own memoirizing ex-wife, Claire Bloom).

Roth’s quasi memoir (a boy named Philip Roth grows up in Newark) comes wrapped in a richly imagined alternate universe: Charles Lindbergh becomes president, keeps America out of World War II, and offers to the nation’s Jews a neighborly hug that slowly becomes a noose.

Roth’s mordant twist on a medieval funeral play, about a man abandoned by all his gifts before death (though here he’s more betrayer than betrayed). A slim, uncompromising fable of a self-centered artist facing the abyss.

The second-wave Roth is prefigured here: metafiction, the tension between high seriousness and bawdy satire, even the first appearance of Nathan Zuckerman.

David Kepesh, five years after his first appearance, in The Breast, is followed from his Borscht Belt childhood into his thirties, by which time his over-the-top sex life is settling into something slightly more mundane. Just about the closest Roth has ever come to writing a happy ending.

By rights, this shouldn’t hold together. There are plot reversals within plot reversals, after which you can’t remember which Zuckerman is dead and which is alive, or which Zuckerman had the anal sex by which he was deemed to have married his exotic bride. But for all the potential confusion, it’s satisfying Roth.

Told almost entirely in dialogue between two adulterous lovers, this is Roth’s smart, stiletto-slim beach-read novel.

The Anatole Broyard story, punctuated by rants about Monica Lewinsky. This Zuckerman-narrated account of an African-American intellectual passing for Jewish is fascinating, but the framing device—the tale of an elderly lecher tortured by p.c. troglodytes—shrivels into self-pity.

This huge first novel contains a lot of what we now recognize as “Philip Roth”: detached Jewish protagonist, marriages ranging from uneasy to horrid, illicit sex (at least by the standards of the day—the book’s set in the fifties). But the voice is curiously neutral, lacking much of the whipped-up frenzy of later Roth.

Pre-Watergate satire featuring Trick E. Dixon, who schemes against Boy Scouts, nukes Copenhagen, and stands up for the voting rights of the unborn. Funny but musty.

David Kepesh makes his debut as a lit scholar (specializing in Kafka) turned overnight into a 155-pound female breast. Naturally, he has a bit to say about that.

Eros and Thanatos are in constant battle in this slenderest of Roth novels—the last Kepesh book—and everyone knows who wins in the end.

No Jews, no Newark, no jokes! You might mistake this for second-tier Updike—especially given that the sex is furtive, guilty, and banal.

This balls-out (as it were) baseball farce is an acquired taste—and even the book’s fans admit it’s too long by a third.