Can AI Bring Students Back to the Great Books?

Is your teenager annoyed by Nietzsche? Confused by Conrad? Through with Thoreau? Now she can talk to the expert inside her e-book.

The creators of a new, artificial-intelligence-assisted publishing effort called Rebind hope that offering interactive, personalized guidance and commentary from well-known writers, scholars and celebrities will help bring classic books alive for students.

They’re also aiming to help adults who might otherwise struggle in solitude through these weighty volumes.

In the process, they predict, the titles could capture a much bigger audience, one that someday may be able to talk back to the experts and even influence how scholars interpret literature. 

The challenge is whether they can make the AI work without being creepy or intrusive.

The price: $29.95 per book, with multi-book subscriptions available. They also plan to offer discounts to schools and find philanthropic partners as underwriters. 

Among the key selling points of Rebind’s e-books is that it offers a clever synthesis of original commentary and “lite” AI that seamlessly matches the experts’ utterances to readers’ queries. So a student studying George Washington’s Farewell Address could pose a question to none other than historian Doris Kearns Goodwin — or at least the version of her already pressed between the covers of an e-book on presidential speeches.

The improbable effort grew out of an equally improbable meeting between the philosopher John Kaag and John Dubuque, great-grandson of the founder of the retail chain Plumbers Supply. Dubuque had spent 14 years as its CEO and sold the company in 2021, at age 38.

Suddenly retired, he set about reading philosopher Martin Heidegger’s famously difficult Being and Time, hiring an Oxford scholar for twice-weekly private tutoring sessions. 

“I had this amazing experience and realized at the end of it, ‘It’s too bad more people can’t access this,’” he said. “This is the only way I ever could have read this book.”

Dubuque also began playing with ChatGPT, asking it to summarize passages from equally difficult books like Alfred North Whitehead’s Process and Reality. He was deeply impressed with the AI, warts and all, and concluded that if someone could tame it for students, cut down on “hallucinations” and focus it on the books, it’d be a game-changer. 

He shared his ideas with Kaag, who had helped him get through William James’ The Varieties of Religious Experience.

Kaag had just published Sick Souls, Healthy Minds: How William James Can Save Your Life, which resonated with his benefactor. Kaag, who as a kid had been a poor reader with a stutter, recounted to Dubuque how his mother would sit at their kitchen table and help him muscle through assignments. 

They realized that many people want to tackle classics like Moby Dick and James Joyce’s Ulysses, Dubuque said, but get intimidated by big, difficult books. “So they just give up and read things that they can read, not the things that they really want to read.”

‘We’re choosing the people — and they’re choosing the books’

Kaag soon recruited his friend Clancy Martin, an author and professor at the University of Missouri in Kansas City, who signed on to help find “Rebinders” for at least 100 AI-assisted e-books, offering readers what amounts to a one-on-one conversation with a novelist, critic or historian about the book.

The endeavor already boasts an impressive stable of author-experts: The Irish novelist John Banville on Joyce’s Dubliners, Goodwin on U.S. Presidents’ speeches, novelist Marlon James on Adventures of Huckleberry Finn, Deepak Chopra on Buddhism and environmentalist Bill McKibben on John Muir.

But there are also some unlikely pairings: Margaret Atwood on A Tale of Two Cities, Roxane Gay on Edith Wharton’s The Age of Innocence, producer, actor and writer Lena Dunham on E. M. Forster’s A Room With a View, and the critic Laura Kipnis on Romeo and Juliet. 

“We’re choosing the people — and they’re choosing the books,” said Martin. 

To avoid copyright fights, the company is limited, for the moment, to books in the public domain, published before 1928. But Rebind is also in conversation with the world’s three largest publishers about offering contemporary books like 1984, Fahrenheit 451 and David Foster Wallace’s 1996 novel Infinite Jest.

Kipnis, who last spring wrote a lengthy account of becoming a Rebinder, has said the endeavor “will radically transform the entire way booklovers read books.”

Acknowledging her misgivings about AI more broadly, she finally admitted to herself that perhaps this particular bet is worth pursuing. “The nihilist in me thinks if humans are going to perish, we might as well perish reading the Classics,” she wrote.

On occasion, Kaag, 44, and Martin, 57, have tried to politely steer a few scholars away from their first choice, with mixed results: When he offered the gig to novelist Garth Greenwell, for instance, Martin promised he could tackle any book he liked. So Greenwell proposed Henry James’ The Golden Bowl — a classic, but not exactly James’ most widely read novel. 

“I said, ‘O.K., Henry James is a great idea,” Martin recalled. “‘What about The Portrait of a Lady?’”

Sorry, Greenwell said. It was The Golden Bowl or nothing. 

Martin threw out a few other titles: The Turn of the Screw? Daisy Miller?

Eventually, he said with a laugh, they resolved it: “He’s doing The Golden Bowl.” 

So far, only a few prominent authors have opted not to participate — the literary novelist Andre Dubus III, a close friend of Kaag’s, told him he was “dancing with the devil.” 

Kaag said he’s getting a mixture of “really good” emails and “really serious hate mail” from colleagues fearful of AI. He takes that fear to heart, having spent much of his career suspicious about ed tech. His classes, he said, have always been “very personal and very one-on-one.”

But he shifted his thinking a few years ago, after suffering from heart troubles that culminated in a cardiac arrest at age 40: “I just thought to myself, ‘I really would like to explore things that I hadn’t explored before.’”

Invoking Dubuque’s intimate tutoring sessions, he thought, “You can only scale one-on-one tutorials, or one-on-one conversations, so far.”

If AI can make that happen and bring the joy of reading to more people, he thought, perhaps it’s worth trying something new. “So to me, I don’t think it’s scary.”

‘Basically every question that I could possibly imagine’

Each book begins with a high-production-value video offering a sneak peak of what lies within. In the case of Henry David Thoreau’s Walden, we get sweeping drone shots of Walden Pond, complete with the Rebinder — in this case Kaag himself — taking a swim. He lives in nearby Concord, Mass., and has taught the book for more than a decade at the University of Massachusetts Lowell. 

For the Walden Rebind, Kaag recorded 30 hours of audio commentary, answering “basically every question that I could possibly imagine” a college student asking. 

The volume of commentary ranges widely, from 10 hours for Dubliners to nearly 80 for Ulysses by the philosopher Philip Kitcher.

As for how Rebind will be used, Kaag sees it not as a replacement for class discussions, but as preparation, a tool that can field questions readers might be too embarrassed to ask in class.

The way Rebind works will be familiar to anyone who reads e-books, but with a revelatory twist: Readers can highlight and annotate text, but they can also open up a chat window anywhere and type or dictate questions about a passage or sentence. They can wonder aloud about ideas or passages they’re curious about, or simply type: “I’m lost.” 

AI analyzes the query and matches it to the pre-loaded commentary, telling readers, if they click on a little icon, which parts of the answer are original and which are the AI smoothing out the syntax to be responsive to the query.

Antero Garcia, an associate professor in the Graduate School of Education at Stanford University and vice president of the National Council of Teachers of English, said he likes the transparency that comes with that breakdown. “I actually hope more AI does something like that, where you can see the sources of things” it presents to readers.

But he worries that tools like Rebind could draw users more into reading as a solitary pursuit. “If I’m lost in Dubliners, that’d be great to go to my English teacher or to a friend and, God forbid, have a reading group or a book group and just have a conversation about this text,” he said. 

Garcia said he was reluctant to overstate the isolating effects of AI, “but I do think there’s something missing as a result of relying on AI to guide us in our reading, rather than relying on reading being an inherently social thing.”

In the long term, Rebind actually seeks to integrate social elements that allow students in a class to “read and work together” within a text. Eventually, they hope to give teachers space for their own commentary. Future versions may offer Rebinders feedback from readers and the opportunity for deeper discussions via AI-moderated book clubs.

One feature stands out as potentially game-changing: If a reader wants to basically journal within the e-book, revealing his or her personal challenges along the way, that prompts the AI to search for commentary that helps: If you’re reading Walden, for instance, and type in, “This book makes me think of my times of loneliness and depression,” the e-book will reply: “I can understand how Thoreau’s reflections on solitude and the challenges of living authentically might resonate with feelings of loneliness and depression.”

That’s then followed up with a brief discussion of Thoreau’s encouragement “to remain attentive, even when things don’t particularly seem bountiful.”

The new e-books will also allow users to take notes, then use them to challenge the Rebinder to a conversation. While that could easily become a big privacy risk, Dubuque said Rebind will never sell user data, since it’s inviting users to “share the deepest, most meaningful things in their life and really give themselves to these books.” Profiting off those details is “not an option.”

‘Dancing with the devil’?

At the moment, the interactions are all through text, but the Rebinders have all given permission to have their voices reproduced so they can someday “chat” directly with users. “We have voice clones,” Dubuque said. “They’re very good.”

But for now audio remains an open question, an option they’re not quite ready to offer. On the one hand, who wouldn’t want to chat about Dubliners with Banville? On the other hand, that could be weird. A small portion of the conversation wouldn’t be Banville at all, but a crusty, Irish-accented Banville-bot.

Dubuque predicted they’ll eventually end up using voice, but he wants to do it carefully.

“We’re very sensitive to the ‘ick factor’ of AI.”

His plan is to release the first books next month. 

Though it’s a for-profit company, with Dubuque its only funder, Martin said he also sees it as an effort to ensure that more young people get the chance to read great books under the guidance of great teachers. “Most of us don’t get to go to Columbia or to Yale or to Princeton,” he said. Fewer still get to study with scholars like Goodwin, Atwood, Banville or Gay.

But Garcia, the Stanford scholar, urged caution.

“There’s something fraught about this pursuit of scale,” he said. “In trying to deliver good books or good learning experiences to people, we ultimately get funneled into this pathway: The way to get it to the most people is to take away that human element or dilute that human element through AI. It feels like that’s when you lose the spirit of it.”

For his part, Martin wants to make Rebind “the most fun, most dynamic and most interesting way” to read books. It won’t supplant the solitary experience of reading, he said, it’ll offer something different: the choice to read a book in solitude or to “have a whole rich conversation about it with someone.” 

Or both. 

Get stories like these delivered straight to your inbox. Sign up for The 74 Newsletter