The Worst Books By the Best Authors

It is said that even a blind pig finds a truffle now and then. That may be true, but writing a good book (despite what so many deluded amateurs seem to believe) is exceedingly difficult. A lousy writer is unlikely, under even the best circumstances, to produce a novel of any value. The reverse, however, unfortunately happens quite easily. The finest writer, if prolific enough, is still practically guaranteed to come up with a couple of duds. Lest anyone mistake the spirit of this inquiry, in which we look at failures on the part of authors whose reputations remain unimpeachable, let it be understood that our choices, though bound to rankle in some cases, are not meant to offend. It may be that we can learn something from great novelists’ misfires, perhaps as much as we can from their successes. Here are 10 cases in point:

  1. Across the River and into the Trees by Ernest Hemingway

    This novel, Hemingway’s sixth, earned him loads of bad press. His then-wife Mary didn’t like it either, for reasons perhaps more personal than aesthetic: it was inspired by Papa’s infatuation with a 19-year-old named Adriana Ivancich. Spoiler alert: Hemingway himself was wounded by the bad reviews and stuck up for his novel, huffing, “they can say anything about nothing happening in Across the River, all that happens is the defense of the lower Piave, the breakthrough in Normandy, the taking of Paris…plus a man who loves a girl and dies.” The next year he would crank out the novella The Old Man and the Sea, which restored his reputation and won him a Pulitzer Prize in 1952 (he would also win the Nobel for his life’s work two years later), but he would never publish any fiction after that, famously committing suicide by shotgun in 1961 following years of declining physical and mental health, exacerbated by FBI harassment and surveillance over his Cuba ties. Across the River and into the Trees has been reevaluated a bit, and Hemingway’s truly shabbiest work is the stuff trotted out after his lifetime, but we’ve made it a point not to include incomplete or posthumous works on this list.

  2. Lady Chatterley’s Lover by D.H. Lawrence

    If this choice proves to be controversial, well, that was the word for Lady Chatterley’s Lover. Originally printed in 1928 by a small Italian press, the book could not be published uncensored in Britain until 1960, when in a highly publicized jury trial, Penguin Books was found not guilty under the 1959 Obscene Publications Act, due to its loophole for works of “literary merit.” While we would argue that this was a splendid blow for free speech, that literary merit can now be separately interrogated. It’s difficult to read the book today with a straight face. The passage of time has taken its toll, surely, but you’re better off skipping to the “good parts,” risible as they are, than sitting through the dialogue in between, largely didactic parlor conversations about politics. There are moments of great writing, because Lawrence was indeed a great writer, but if that (rather than historical or prurient reasons) is what you’re reading him for, start with Sons and Lovers, Women in Love, or better yet, the short stories.

  3. Terrorist by John Updike

    Updike, longtime chronicler of suburban angst, turned to the realm of geopolitics in his old age to make a play for post-9/11 relevance, with this novel about a homegrown Muslim militant in New Jersey. Unfortunately, though Updike’s effort to get inside the head of an angry and disaffected youth from another ethnicity and faith is admirable, it tends to come off as somewhat tone-deaf. Likewise, the long didactic explications of Islamic theology might be edifying and de-parochializing for his audience, but in the context of a novel they seem leaden and programmatic.

  4. I Am Charlotte Simmons by Tom Wolfe

    If Updike’s stint as a jihadi was well-meant but unsuccessful, Tom Wolfe’s examination of the sex lives of modern college students was flat-out embarrassing. His 2000 essay collection Hooking Up laid much of the groundwork for this 2004 novel, and Wolfe’s “research” seems to have been intensive. Imagine him hanging out at frat parties, in his trademark white suit, scribbling in a notepad while he watched kids playing beer pong or making out, like Margaret Mead among the Samoans. Creepy, is the word for it, and, like the worst criticisms of Mead have it, he projected his most prurient fantasies onto these coeds, resulting in a dubious honor: Literary Review‘s Bad Sex in Fiction award (which was actually kind of the point of those scenes).

  5. Hawkes Harbor by S.E. Hinton

    The Outsiders was Hinton’s first novel, written when she was in high school, and perhaps that’s why it resonated so strongly with a generation of young-adult readers. It was also responsible, along with follow-up Rumble Fish, for launching the careers of a wave of young actors in the 1980s, when Hinton’s books were filmed by Francis Ford Coppola. Unfortunately (this may count as a spoiler), Hawkes Harbor, her first book in over a decade, seems to count for inspiration not on Hinton’s lived experience, like her best work, but on Hollywood, specifically schlocky ‘70s television. Not only is the main character named Jamie Sommers (like TV’s Bionic Woman), but halfway through the book turns into a vampire novel, possibly even conceived as Dark Shadows fan fiction.

  6. Deadeye Dick by Kurt Vonnegut

    Some might nominate Slapstick for this slot. Vonnegut himself gave that novel the lowest grade, a “D,” in a retrospective self-assessment he published the year before Deadeye Dick. When great authors go wrong, it’s often through an exaggeration of the qualities that made them special to begin with. In Dick, Vonnegut is tackling his usual theme, how humanity can overcome despair in a world of self-inflicted holocausts, both nuclear and personal. But he doesn’t quite get there, and here his cynicism overcomes his sweetness, which may be philosophically justified but it makes for a tough slog.

  7. The Violent Bear It Away by Flannery O’Connor

    Speaking of writers who repeat themselves endlessly and occasionally lose control, O’Connor, in her second novel (her only one after Wise Blood) takes her religious proselytizing, dark irony, and Southern Gothic grotesquery even further than usual. The main character resists his destiny as successor of his great-uncle Mason Tarwater, a raving fundamentalist prophet (who O’Connor herself saw as the most sympathetic character), but comes around to it in the end. It may not count as a bad book per se, but even to avid admirers of her ingenious and passionate short stories, it may seem like a long and unpleasant harangue.

  8. Tarantula by Bob Dylan

    Yes, that Bob Dylan. His 2004 memoir Chronicles, Volume One was a finalist for the National Book Critics Circle prize (we’re eagerly awaiting volumes two and three). He’s been tipped as a contender for the Nobel Prize in Literature for a couple of years now, presumably on the strength of his song lyrics. Dylan’s words have enriched the language and culture to an incredible degree, steeped as they were in deep study of American folk traditions, microfilm of 19th-century newspapers, French symbolist poets and his own friends in the Beat-era avant garde. Around the same time that all these influences came together to inspire Dylan’s best music in the mid-1960s, he wrote a book called Tarantula. As Dylan put it himself, “Things were running wild at that point. It never was my intention to write a book.” It was not well-received when it was officially published in 1971 after years of literary bootlegs. A highly experimental work, perhaps it can be thoughtfully decoded like Finnegans Wake by those who care to spend a lifetime doing so, but as a novel, it’s pretty unreadable.

  9. The Almost Moon by Alice Sebold

    After her harrowing memoir Lucky and bestselling The Lovely Bones were received with rapturous acclaim, Sebold’s sophomore novel came as a great disappointment. The dreaded “sophomore slump” is a real phenomenon, and the pressure after The Lovely Bones must have been enormous. Spoiler alert: what Sebold does in The Almost Moon is in its way as daring as her dead narrator in the previous book, having us identify with a protagonist who kills her own mother, but the story just doesn’t hold together on an emotional level, and the book left many readers confused or annoyed.

  10. The Marriage Plot by Jeffrey Eugenides

    Another very talented contemporary novelist, Eugenides debuted The Marriage Plot to huge anticipation and industry fanfare after the critical triumphs of The Virgin Suicides and Middlesex. Alas, the characters that populate the book are a bunch of English majors endlessly dissecting literary theory and their own love lives … the kind of subject that usually occupies a first novel, not a third, especially when the first two demonstrated such imagination and versatility.