The 6 Sexiest Philip Roth Novels

Photo: Andreas-Saldavs, Getty Images.

If you happened to sleep through the English Lit class in which Philip Roth was assigned, consider this your wake-up call. The New Jersey novelist wrote some of the most provocative, sexually-charged novels of the 20th Century with darkly comic wit. May-December infatuations, threesomes, and adultery were just a few of Roth’s favorite themes. The following books (some of them semi-autobiographical) are among the most erotic and deliciously deviant of the controversial author’s oeuvre.

The Professor of Desire (1977)

David Kepesh’s craving “knows no bounds.” At college, he picks up chicks in the reading room of the library, dropping lines like “Your ass is a masterpiece.” Alas, he’s mostly unsuccessful with the ladies, but the tide changes when Kepesh arrives in London for a fellowship year. There, he meets Elisabeth and Birgitta, a pair of young Swedish women, and begins dating the former. It isn’t long before a BDSM-tinged threesome ensues, as do complications and unintended consequences of the trio’s trysts. Ultimately, Kepesh departs for California, and there he weds Helen, a woman trying to move on after a disastrous affair with a married man. It isn’t long before they’re arguing over trivial topics like toast and taking out the garbage. The relationship deteriorates, and Helen takes off, but Professor Kepesh won’t be alone for long.

During a weekend on Cape Cod he meets Claire, a wholesome teacher devoted “to the ordinary business of daily life.” They enjoy simple pleasures together: books, nature walks, photography, picnic lunches, and “Sundays when we would cling together in my bed until three in the afternoon.” But one summer day, a phone call interrupts their bliss. It’s Helen, asking if she — and her new husband — can stop by for a visit. Truths are shared between the ex-spouses, and a secret the seemingly innocent Claire has been keeping comes to light. Will the idyllic couple of Claire and Kepesh survive? You decide: the book ends with an early morning scene of Kepesh contemplating the complexities of love while suckling Claire’s breasts.

The Dying Animal (2001)

David Kepesh, who we met in The Professor of Desire, is back. He’s older, though who knows how much wiser. His relationship with the beloved Claire did not work out, and Kepesh now has his sights set on a student, Consuela, a Cuban woman with “round, full, perfect” breasts and “nearly pornographic underwear.” After sleeping with her the first time, Kepesh gushes, “With a self-contained woman of such sexual power, you have no idea and you never will.”

The 62-year-old professor has a lot of fun teaching his 24-year-old student how to be his filthy little whore, detailing their adventures in everything from mouth-fucking to menstrual voyeurism. The side effect of all this “harmonious hedonism”, however, is crippling jealousy. Citing cultural differences, Consuela refuses to be in a publicly recognized relationship with Kepesh, a restriction that drives him insane.

It takes about 18 months for the fling with Consuela to run its course, and twice that amount of time for Kepesh to recover from it. Years pass. Kepesh continues to fuck his students and console exes that resurface, complaining, “Dating is hateful, relationships are impossible, sex is a hazard.” Then Consuela reappears, with devastating news and a favor to ask of Kepesh. Will their flame reignite? Or will this be the professor’s undoing?

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Deception (1990)

Two lovers in a room, talking. That’s the entire premise of this sparse but intimate novel. Philip is an American writer living in London; his lover is a married Englishwoman who is at once eager and reluctant to leave her husband. The economy of language Roth employs is one of the great joys of this book. Chapters are divided into sections, presumably to represent snippets from each encounter. One section: “Undressing him. ‘This is a new belt.'” Another: “‘Honestly, I swear to you that it’s true. I never masturbated until I was twenty-seven.’ ‘Poor you.'”

Over the course of the book, the lovers discuss their affair, gender roles, sexual histories, and cultural backgrounds. They role-play. They debate. Dialogue is not attributed to either character, but the context allows the reader to divine who is speaking. It is a tender and fraught story, so true-to-life it’s almost as if you were reading Roth’s expertly edited transcript of his own affair. Indeed, the last chapter of Deception will leave you wondering if that’s exactly what this is.

Sabbath’s Theater (1995)

Mickey Sabbath is a dirty old man. At the start of this National Book Award-winning novel, the 64-year-old former puppeteer is fucking Drenka, a married, 52-year-old woman with “uberous” breasts. When Sabbath tries to negotiate a threesome between himself, Drenka, and a young German au pair, Drenka declares, “I don’t want to be treated like a fake whore. I want to be treated like a real whore. A thousand dollars or I stay home.” It is only the first of many lascivious deals to be floated between the couple.

Drenka is a demanding woman, but money isn’t really what she longs for; fidelity is. “You want monogamy outside marriage and adultery inside marriage,” Sabbath marvels at his lover’s request. They come close to an agreement: he will stay faithful to her if she gives her husband head twice a week. All this is for naught, however, because Drenka drops dead six months later.

All of the above happens within the first 33 pages of Sabbath’s Theater. The story only gets more outrageous, uncensored, and despairing over the subsequent 400+ pages as Sabbath revisits former conquests, indignities, and philosophies that have lorded over his life. (“You must devote yourself to fucking the way a monk devotes himself to God” is just one of his commandments.) Tales of phone sex, anal sex, and prostitution titillate but can’t distract from the fact that death hovers a little too close for comfort. Could it be that Sabbath is using sex to stave off mortality?

Indignation (2008)

If you’ve seen the recently released film adaptation of Indignation, don’t let it prevent you from picking up the book, which is far sultrier than what transpired on-screen. (The New Yorker went so far as to call the film adaptation “sterilized”.) Set in 1951, the novel follows Marcus Messner, a butcher’s son, as he attempts to navigate religious politics at Winesburg College. (Fret not, things heat up. No one does sexual tension better than the repressed!)

Enter Olivia: a fellow student, child of divorce, and suicide attempt survivor who gives Messner his very first blow job. This unexpected rite of passage begins to fuck with his head (no pun intended) and the couple go back and forth about whether or not they can continue to see one another. Though others tell Messner that (to paraphrase) hot bitches always be crazy, he can’t stop obsessing about her…and the feeling appears to be mutual. When Messner ends up in the hospital, Olivia is his first visitor, and she cares for her patient by giving him a discreet hand-job. But just when Messner couldn’t be more entranced by this shikse, his mother intervenes, and makes him an ultimatum he can’t refuse. The repercussions will haunt him for the rest of his life.

The Humbling (2009)

Sex and death go together like…well, nothing else, really. These strange bedfellows dominate this brisk and brutally honest novel about a 65-year-old actor, Simon Axler, who suddenly loses his theatrical prowess, after which his wife abandons him. Suicidal, Axler checks himself into a mental hospital. Upon his release, he reunites with 40-year-old Pegeen, the daughter of friends, described as a “full-breasted woman” who enters Axler’s life with “the invulnerable air of a happy person”. Fresh off a breakup, Pegeen decides that after 17 years of living as a lesbian, she now wants to be with a man. Axler joyfully offers to be her lover, and the two fall into a sexually experimental relationship. At one point, Pegeen dons a strap-on leather harness and green dildo for Axler’s amusement. “You’re…a very twisted man to be turned on by a girl like me,” she tells him. He agrees.

This bliss doesn’t last, however, and soon one of Pegeen’s exes begins terrorizing the couple and Pegeen’s parents via telephone. Pegeen’s mother vehemently objects to the dalliance between her daughter and Axler and Axler fears that he’s going to be Pegeen’s next “reproachful, crazed, avenging ex”. We won’t divulge whether or not this novel results in a literal happy ending or a metaphorical one, but the last page is downright explosive.