Looking for the best Philip Roth books? You’ve come to the right place. Roth is arguably the best American novelist of the 20th century. Between Goodbye, Columbus in 1959 and Nemesis in 2010, Roth published 27 novels and four books of nonfiction, and he won three PEN/Faulkner Awards, two National Book Awards, two National Book Critics Circle Awards, two WH Smith Literary Awards, a Pulitzer Prize, the Man Booker International Prize, the PEN/Nabokov Award, the Franz Kafka Award, the National Book Foundation Medal for Distinguished Contribution to American Letters, a Gold Medal in Fiction from the American Academy of Arts and Letters, and the 2010 National Humanities Medal given by Barack Obama in the East Room of the White House. Whew.
In a 2006 New York Times Book Review poll of writers, critics, and editors regarding the “single best work of American fiction published in the past 25 years,” six of Roth’s novels made the cut, more than anyone else. Critic A.O. Scott noted, “If we had asked for the single best writer of fiction of the past 25 years, he would have won.”
Dude’s got credentials. But it’s more than that. For me, it’s Roth’s unparalleled voice that nudges him above the rest. His sentences are stunning feats of style and rhythm, whether he’s reproducing free-associative speech (as in Portnoy’s Complaint), parodying the tergiversating tap-dance of “real politik-ese” (in Our Gang), or his masterful use of third-person limited (Zuckerman Bound, Everyman, etc.).
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Among his novels are satires, romps, dramas, alternate histories, metafictional experiments, meditative explorations, period pieces, and grand indictments of the American century. Like his cinematic counterpart, Woody Allen, Roth’s fiction is assumed to be repetitive (an opinion captured by Australian publisher and critic Carmen Callil, one of the judges for the Man Booker International Prize, who withdrew from the panel because Roth “goes on and on and on about the same subject in almost every single book”), but even a cursory glance at his oeuvre renders that argument moot.
But that doesn’t mean Roth doesn’t have his recurring themes, as every artist does. And one of his most prominent subjects is the emotional and intellectual life of a writer. When I first encountered Roth’s Zuckerman novels, I felt such a sense of relief that I wasn’t the only one who thought and felt these things. He was a novelist dedicated to the art of fiction, and his commitment produced some of the most illuminating and engaging books in the past 50 years. So what if like all creative people he returns to certain themes? Like Zuckerman writes in The Prague Orgy, “No, one’s story isn’t a skin to be shed—it’s inescapable, one’s body and blood.”
Because Roth is such an important writer, and because he wrote so many books, I thought it would be a wonderful service to rank all of his novels, so that any interested reader might use it as guidance for breaking into the astounding catalog of an American icon. This list is entirely my opinion, with little or no consideration for acclaim, historical importance, or artistic breakthroughs. My rankings are purely based on readability, insight, stimulation, and entertainment.
There are endless ways to approach Roth’s library, just as there are endless ways to order the list, but I thought the most useful thing would be to think in terms of broad recommendations, aimed to satisfy the maximum amount of readers. I now present: The Ranking of Philip Roth.
Roth’s coarsest, frankest, and most exhilarating novel, Sabbath’s Theater shows off Roth’s linguistic verve, his brilliant characterization, and his unparalleled ability to stare unblinkingly into the psyche of a depraved scoundrel. Even Roth’s most scathing critics wouldn’t argue that Mickey Sabbath, once-famed puppeteer and now aging misanthrope, functions as a Roth stand-in. No, Mickey Sabbath is entirely imaginative, and what a creation he is! And not merely in character but in voice; the prose of Sabbath’s Theater is Roth’s most energetic, the most successful of his more exuberant and stylized prose (as opposed, e.g., from the pure eloquence of Everyman). Winner of the National Book Award, it is a work that James Wood called “a passionate, intensely funny, repellent, and very moving portrait of the scandal of male sexuality.” Sabbath does not earn our sympathy, only our understanding, and his fate is that of all men who equate sexual libidinousness with vitality. Sabbath’s Theater is the best of what Roth can do: bring us down into the deepest caverns of the savage mind of men and guide us through its horrors before yanking us out again to show the body in which such a mind is housed—that of a feeble old man with nothing left but his own bitterness. (1995)
The PEN/Faulkner Award-winning Everyman is the first in a quartet of short novels Roth refers to as “Nemeses,” followed by Indignation, The Humbling, and Nemesis, but Everyman is the best of the series. It is, in a certain way, the perfect distillation of Roth’s talents, as the unnamed protagonist of the novel isn’t an inherently fascinating character. He’s, obviously, an everyman, and the narrative traces the various bouts with sickness and mortality of his life. That’s it. Yet Everyman is a stunning, meditative, and, most importantly, hugely entertaining novel, showcasing Roth’s uncanny ability to render the everyday into literary gold. (2006)
Beginning with The Ghost Writer and continuing with Zuckerman Unbound, The Anatomy Lesson, and a coda novella, The Prague Orgy, the Zuckerman Bound novels introduced the world to Nathan Zuckerman, Roth’s longtime fictional alter ego (though the name Nathan Zuckerman first appears in My Life as a Man as an alter ego of Peter Tarnopol, a novelist and an early Roth stand-in himself), who is either the protagonist or narrator for many of Roth’s greatest works. Through Zuckerman, Roth examines every aspect of his life as a novelist—ambition, fame, money, fans—but also nails the way that being a writer makes one see the world—that is, as Zuckerman says in The Anatomy Lesson, “that all the world’s suffering is good to me inasmuch as it’s grist to my mill—that all I can do, when confronted with anyone’s story, is to wish to turn it into material.” Roth explored this theme less directly in other novels, but Zuckerman Bound, for me, captures Roth’s autobiographical idiosyncrasies and his bracing honesty better than anything else he wrote. (1979, 81, 83, 85)
When American Pastoral won the Pulitzer Prize in 1997, the award was an exclamation point on Roth’s unprecedented feat in the 90s: from 1991 to 1997, Roth won the National Books Critic Circle Award, the PEN/Faulkner Award, the National Book Award, and Pulitzer in a row. No other American author has even come close to such a streak. The story of Swede Levov and his daughter’s radical political terrorism in 1968, American Pastoral inaugurated Roth’s America trilogy and was followed by I Married a Communist and The Human Stain. Narrated by Zuckerman, it is a rich tapestry of moral paradox and wrenching familial calamity, and features one of my very favorite final sentences in contemporary fiction. (1997)
Roth’s first book, the title novella and five stories, earned him much critical praise as well as the ire of many Jews who viewed his fiction as anti-Semitic. The story “Defender of the Faith,” about an army sergeant who refuses clannish special treatment to a fellow Jew by sending him to the front line, particularly caused a controversy when it first appeared in The New Yorker in 1959, but the 26-year-old writer received support from the literary world in the form of the 1960 National Book Award, and from what Roth called the “four tigers of American Jewish literature,” Saul Bellow, Alfred Kazin, Leslie Fiedler, and Irving Howe, who opened his review of Goodbye, Columbus with this almost hyperbolic acclaim: “What many writers spend a lifetime searching for—a unique voice, a secure rhythm, a distinctive subject—seem to have come to Philip Roth totally and immediately.” Despite the success of the book, its reception among the Jewish community rattled young Roth, who once vowed, after an acrimonious crowd ambushed him after a speaking engagement, “I’ll never write about Jews again.” Way to stick to your guns, there, Phil. (1959)
One of Roth’s most ambitious and inventive novels, The Counterlife takes Zuckerman out of the restraints (it unbounds him, one might say) and into a meta-novel unlike any other. The plots—if you can call them that—of the five sections contradict each other, so, e.g., the death of Zuckerman’s brother Henry in the first part never happened in the second. Instead, Henry survives the surgery that killed him in chapter one and flees to Jerusalem in an existential funk. In another episode, it’s Zuckerman who has the surgery and dies from complications that arise, and the previous chapters are found to be the last novel Zuckerman was working on before his death. The Counterlife is daringly experimental and multitudinous, simultaneously a study of the fictional enterprise and the endless ways a story can be told, as well as an analysis of our lives’ divergent paths, how arbitrary they can be and yet how final, how our what-might-have-beens can be as complex as how things are. (1986)
If Goodbye, Columbus established Roth as an emerging writer to watch, it wasn’t until a decade later that he became a literary sensation (though, again, a controversial one) with the publication of Portnoy’s Complaint, a tour-de-force monologue from one Alexander Portnoy, a neurotic young Jew obsessed with his own sexual perversions and their relation to his feelings about his mother. The novel takes the form of a session of psychoanalysis, ostensibly making Portnoy’s words all the more confessional and unfiltered, and the title comes from the disorder the analyst names after his patient, “in which strongly felt ethical and altruistic impulses are perpetually warring with extreme sexual longings, often of a perverse nature.” It’s a very funny work, though much of its outrageousness has obviously been tempered by time. What’s notable about Portnoy’s Complaint is the voice, the popping, dancing, rhythmic bounce of Roth’s prose, a breakthrough for Roth as a literary artist and important milestone in fictional technique. As Claudia Roth Pierpont so succinctly put it, “If Holden Caulfield ever behaved like this, he didn’t tell us about it.” (1969)
Roth believed that Operation Shylock: A Confession would be his masterpiece, and in many ways it is. Certainly, his best use of autobiography and his most incisive use of meta-techniques, the novel pits Philip Roth against an imposter, a man going around using Roth’s name and identity to proselytize about the necessity for Jews to return to Europe. In real life, Roth underwent a surgery for his knee that left him with more chronic pain that before, and the medication he was given—a notoriously problematic sleep-aid Halcion—induced a near mental breakdown that included hallucinations and a perceived loss of identity. This “disintegration,” as he calls it, forced Roth to rethink his life and purpose, and also lead to the most creatively successful and intellectually challenging run of books he would ever produce, beginning with the nonfiction books The Facts: A Novelist’s Autobiography and Patrimony, and soon Roth found himself in his own novels, in Deception and then Operation Shylock. His use of doppelgangers no longer seemed suitable, as his crisis was not one of creator vs. his creations, but a man and himself. It is an astonishing accomplishment, and one made all the more impressive by the fact that it stemmed from Roth’s painfully horrendous experiences. He certainly came out anew on the other end of that nightmare. (1993)
A hugely ambitious undertaking, The Plot Against America is a revisionist take on 20th-century history. In Roth’s version, aviation hero and über-anti-Semite Charles Lindbergh wins the Republican nomination for President during the 1940 election and defeats Franklin Roosevelt. The story is told through the Roth family, narrated by young Philip, a technique which personalizes the historical significance of Lindbergh’s landslide victory, so the impact of his subsequent (and totally horrifying) acts as President—e.g., a treaty with Hitler, promising that the U.S. wouldn’t interfere with German expansion in Europe—play out the novelist’s biography. It is an alternative history but also an alternative memoir, a re-imagining of his own life through the bewildering prism of the hypothetical. (2004)
10. The Human Stain
The late-90s parable of Coleman Silk, forced out of his position as dean of a college faculty because of an innocuous remark that was interpreted as racist, and his life-long secret that shocks everyone, is one of Roth’s most complex moral conundrums. That the story is concurrent with the real-life scandal of Bill Clinton’s extramarital affair with Monica Lewinsky adds a wider component to its cultural implications (especially since Zuckerman, the narrator, first finds himself in Coleman’s confidences because of an affair he’s having with his housecleaner). But it is Coleman’s undisclosed revelation (which, of course, I won’t give away) that pushes The Human Stain into the realm of classic fiction—or, at least, it strikes numerous disparate notes that make up a uniquely American chord. (2000)
11. Our Gang
Rereading Our Gang in the time of Donald Trump’s presidential campaign shows just how prescient of a satire it is. A savage attack on Nixon, the novel centers on Trick E. Dixon, a tap-dancing, tergiversating politician who with smarmy smugness and almost blatant hypocrisy expounds on, e.g., the “sanctity of human life,” including the unborn, while dodging questions about the murder of a pregnant woman by American forces in Mỹ Lai. It is a very funny book, and Tricky’s motif of reminding citizens that he was a lawyer and thus different from other Washington politicians rings a very familiar bell, albeit a maddening and worrisome one, so when Tricky is assassinated and, wasting no time at all, runs for the position of Devil in Hell, Our Gang’s clever mockeries, and apoplectic rage make it a unique and fascinating entry to Roth’s wildly eclectic library. (1971)
The second in the America trilogy, I Married a Communist, set during the 30s through the 50s, is a period piece but also a response to Roth’s ex-wife’s tell-all book, Leaving a Doll’s House. Some even referred to it as a “revenge novel,” as the depiction of radio star Ira Ringold’s wife Eve struck many as a thinly-veiled version of Claire Bloom. Private motivations notwithstanding, I Married a Communist is a fantastic evocation of the Red Scare and the American madness that followed. And even Ira’s tempestuous marriage to Eve isn’t blandly one-sided; Roth, at the very least, is usually too interesting a fiction writer for that. Eve even winds up a sympathetic character, and Ira equally as indicted in their flagrantly contentious romance. Plus, the form of the novel—a long conversation between Zuckerman, our trusty narrator, and Murray Ringold, Ira’s brother—allows for numerous insights of those looking back with astonishment the world that had previously existed. (1998)
13. Exit Ghost
The final Zuckerman novel inverts the first one: instead of, as in The Ghost Writer, a young person from New York City traveling to the country to visit an aging novelist, in Exit Ghost we have an aging novelist coming to the city and interacting with the young. The world, of course, looks nothing like the one he left behind eleven years earlier, and Zuckerman, the once-great chronicler of society’s sexual mores, finds himself out of his league. Though I personally enjoyed this novel very much, it is pretty much only for those who’ve read Zuckerman Bound and The Counterlife, so its potential readership is limited. But if you’ve come this far with Zuckerman, Exit Ghost is a lovely and elegiac finale for one of literature’s most enduring characters. (2007)
The final short novel of the Nemeses quartet, Nemesis is also Roth’s final novel in general. (After it was published, he announced that he was retiring from fiction writing.) In Newark, NJ (Roth’s hometown and the setting of many of his novels) during the polio scare in the summer of 1944, a young man named Bucky Cantor tries valiantly to navigate the harrowing effects of the deadly pestilence. A weightlifter and javelin thrower (his poor eyesight’s the only reason he’s not fighting in the war), Bucky is popular among the neighborhood kids he looks after on the playground, and as more and more people flee the city for the safety of the country, Bucky resists leaving until his girlfriend convinces him to join her at Indian Hill, a summer camp in the Poconos. Nemesis moves into the future by the novel’s end, and, even more than in American Pastoral, the last whole paragraph of the novel is Roth’s very best—an appropriate conclusion to an unrivaled career. (2010)
Another of the Nemeses quartet, this one about a young Newark kid attending Winesburg College in Ohio (the nod to Sherwood Anderson makes pretty clear what Roth’s up to), getting involved with a sexually mature girl (Roth’s men, though often indicative of patriarchy, are just as often in way over their heads with the women they’re involved with), and the clashes with the school’s Dean that ensue. The theme of Indignation is the caprice of our decisions, “of the terrible, the incomprehensible way one’s most banal, incidental, even comical choices achieve the most disproportionate result,” and though it’s a readable and mostly engaging novel, it doesn’t have the parable impact of Nemesis or the diamond-hard humanity of Everyman (though it is miles beyond the other entry in the quartet, The Humbling). (2008)
16. The Dying Animal
Aging critic and professor David Kepesh has always had affairs with his students, but his romance with Consuela Castillo plunges him into a state of obsession and jealousy. Though like The Humbling in its chauvinist use of a woman as a means of male salvation, at least this one seems like the overdue comeuppance of Kepesh’s lascivious practices and less like some last exposure to “beauty” or “ecstasy” (whatever euphemism often used for misogyny) before croaking. Consuela, here, is in control of the relationship, and Kepesh winds up a drooling, sycophantic devotee of the 24-year-old, a foolish old man getting what he deserves. It’s not a masterpiece, but it’s the most tolerable of the woe-is-my-elderly-penis tales because here the woe isn’t taken as seriously. Men like Kepesh are dying animals, the novel claims, and let’s hope its predicted extinction comes to fruition sometime soon. (2001)
17. The Breast
The slim novel The Breast is notable for two reasons. First, it is the first appearance of David Kepesh, another one of Roth’s recurring characters; and second, it’s Roth’s only novel to employ legit magical realism. In the tradition of Kafka’s “The Metamorphosis” and Gogol’s “The Nose,” The Breast is about a man who overnight turns into a giant breast. The result is a fun, if slight, Rothian romp on sex, the body, and the delusions we create to face the absurdities of reality. (1972)
18. My Life as a Man
After the breakthrough of Portnoy’s Complaint, Roth underwent a period of eclectic experimentation: from the political satire Our Gang to the mega literary parody The Great American Novel to this meta-fictional work that pairs the life of novelist Peter Tarnopol with the biography of his fictional alter ego, Nathan Zuckerman. After first being presented with two of Tarnopol’s stories, the second half of the book has Tarnopol explaining his frustration with both his adult existence and his inability to come to grips with it through his fiction. My Life as a Man clearly shows Roth in the midst of another major discovery—that is, the utility of autobiography and meta-fiction—but there’s a sense, when compared to his later efforts, of unwieldiness, as if, like Tarnopol himself, Roth was unable to wrangle his ambitious ideas into a satisfying narrative. Later in his career, he would achieve this time and time again, with Zuckerman Bound, The Counterlife, and Operation Shylock, but My Life as a Man, though gripping and fascinating in its own way, doesn’t quite cohere as effectively. (1974)
19. Letting Go
Roth’s first proper novel is a long and ultimately laborious attempt at Jamesian seriousness and depth. The story of two young men in the late 50s, a writer and a scholar, and how their duty-driven definitions of manhood force them into moral situations they are unequipped to deal with, Letting Go was a necessary step for Roth’s creative progress but not particularly essential for a reading, when deciding amongst his repertoire. There are flashes of later, self-assured Roth in Letting Go, but at over 600 pages, it’s probably best to experience his brilliance elsewhere. (1962)
Roth plucks literature professor David Kepesh from the Kafkaesque nightmare of turning into a giant breast and puts him into the Kafkaesque misery of life. Or at least that’s how Kepesh sees it. The novel follows the numerous temptations of Kepesh’s life—from a childhood desire to sleeping with his college students—and becomes one of those, “Oh what am I supposed to do? I’m married to a beautiful woman but what about sexual passion? What about excitement? What about that woman right there? Oh, the humanity!” kind of novels. (1977)
Employing the tropes of the mythic “Great American Novel” to tell a story deserving of such pompous, Great-American-Novel-ness: baseball. It’s a self-conscious parody of literary and American ambition (it’s opening line echoes Moby-Dick’s: “Call me Schmitty”), and Roth shows off his verbal acrobatics, but the wide cast of broadly drawn characters prove that Roth is much better when he mines the multiplicities of one or a few characters rather than surveying the mad intersections of the picaresque via many. It’s a fun novel, but as it itself suggests of those who genuinely aimed to write the Great American Novel, it’s a bit of misplaced ambition. (1973)
Unfolding entirely through dialogue, Deception is a strange moral experience. The protagonist is a novelist named Philip Roth who lives in London with his English wife, which was exactly true of the real Roth at the time. The conversations, though, are not with his wife but with a woman he’s having an affair with, and much of the conversation revolves around Philip’s wife having read his recent fiction—which is the very novel we’re reading—and getting upset with him for cheating on her. He denies the accusation indignantly, and eventually she believes him—but of course, we know that he is having an affair and that the conversations taken basically verbatim from actual conversations. Given that we know that Roth (the real one) did actually show his wife Claire Bloom (revealed in elaborately damning detail in her memoir Leaving a Doll’s House) the manuscript for Deception and she actually did get super pissed about it (the unnamed wife in the book was originally named Claire, until she demanded he take it out), and given the fact that the fictional wife is portrayed as an unexciting, monotonous obstacle, the whole thing feels icky and mean-spirited and weird. Roth does provide some reprieve and some narrative intention by trying to turn the affair into a poignant love story (which he almost does), but it’s still too bare and personal to succeed as fiction. (1990)
Like Letting Go, Roth’s second novel reads like a young author testing out his range—or, as is the case with When She Was Good, his restraint. With a woman protagonist based on his ex-wife at its center and a cast of Midwesterners orbiting around her forceful ambitions and unwavering rage at the hapless men in her life. Though not as one-note or as indelicately rendered as you might imagine, Lucy Nelson and the town of Liberty Center is too austere and mirthless to come fully to life. When interviewed for Claudia Roth Pierpont’s absolutely fantastic Roth Unbound, the novelist still “takes satisfaction that he pulled it off.” If by pulling it off he means “adhere to the strict austerity in technique throughout the whole thing,” then, yeah, he totally pulled it off, but if he meant “made the novel work as a great piece of fiction,” then…no, no, he did not quite do that. (1967)
24. The Humbling
For me, this is Roth’s worst novel. The story of a once-great actor who “loses his magic,” which is apparently a euphemism for “mojo” because the aging thespian’s revival comes in the form of a sexually adventurous affair with a young lesbian, The Humbling is one of the few times it seems like Roth’s doing what his most vituperative critics accuse him of: using fiction as a pretense to exercise his own amorous (and also totally predictable and immature and preposterous) fantasies. The ending, too, is hollow and over-determined and basically without any meaningful connection to the real world. (2009)