The creators of a new, artificial-intelligence-assisted publishing effort called 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 could pose a question to none other than historian — 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 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 “” 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 on Adventures of Huckleberry Finn, Deepak Chopra on Buddhism and environmentalist 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 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 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 , 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.”&�Բ�����;

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.”&�Բ�����;

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 . 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 .

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.”&�Բ�����;

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.”&�Բ�����;

Or both. 

If you went to high school in the United States anytime since the 1960s, you were likely assigned some of the following books: Shakespeare’s “Romeo and Juliet,” “Julius Caesar” and “Macbeth”; John Steinbeck’s “Of Mice and Men”; F. Scott Fitzgerald’s “The Great Gatsby”; Harper Lee’s “To Kill a Mockingbird”; and William Golding’s “The Lord of the Flies.”

For many former students, these books and other so-called “classics” represent high school English. But despite the efforts of reformers, both and , the most frequently assigned titles have never represented America’s diverse student body.

Why did these books become classics in the U.S.? How have they withstood challenges to their status? And will they continue to dominate high school reading lists? Or will they be replaced by a different set of books that will become classics for students in the 21st century?

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The high school canon

The set of books that is taught again and again, broadly across the country, is referred to by literature scholars and English teachers as “the canon.”

The high school canon has been shaped by many factors. Shakespeare’s plays, especially “Macbeth” and “Julius Caesar,” have been taught consistently , when the curriculum was determined by college entrance requirements. Others, like “To Kill a Mockingbird,” winner of the 1961 Pulitzer Prize for fiction, were ushered into the classroom by current events – in the case of Lee’s book, . Some books just seem especially suited for classroom teaching: “Of Mice and Men” has a straightforward plot, easily identifiable themes and is under 100 pages long.

Titles become “traditional” when they are passed down through generations. As the education historian Jonna Perrillo observes, of having their children study the same books that they once did.

The last period of significant change to the canon was during the 1960s and 1970s, when the largest generation of the 20th century, the baby boomers, went to high school. For instance, in 1963, at Evanston Township High School in Illinois revealed that “To Kill a Mockingbird,” first published in 1960, was by far the “most enjoyed book,” followed by two books that had been published in the 1950s, J.D. Salinger’s “The Catcher in the Rye” and Golding’s “The Lord of the Flies.” None of these books were yet traditional, yet they became so for the next generation.

A comparison of national surveys conducted in 1963 and 1988 shows how several books that were introduced to the classroom when the boomers were students had become classics when boomers were teachers.

During the 1960s and 1970s, teachers even reframed “Romeo and Juliet” as a contemporary work. Lesson plans from the era referred to its adaptations into “” – a musical that – and Franco Zefferelli’s of Shakespeare’s story of star-crossed lovers. It became the perfect hook for ninth graders in a study of Shakespeare that would conclude in 12th grade with “Macbeth.”

Efforts to diversify

English education professor that, since the 1960s, “leaders in the profession of English teaching have tried to broaden the curriculum to include more selections by women and minority authors.” But in the late 1980s, according to his findings, the high school “top ten” still included only one book by a woman – Lee’s “To Kill a Mockingbird” – and none by minority authors.

At that time, a was underway about whether America was a “melting pot” in which many cultures became one, or a colorful “mosaic” in which many cultures coexisted. Proponents of the latter view argued for a multicultural canon, but they were ultimately unable to establish one. A 2011 survey of Southern schools by Joyce Stallworth and Louel C. Gibbons, published in “English Leadership Quarterly,” found that the five most frequently taught books were all traditional selections: “The Great Gatsby,” “Romeo and Juliet,” Homer’s “The Odyssey,” Arthur Miller’s “The Crucible” and “To Kill a Mockingbird.”

One explanation for this persistence is that the canon is not simply a list: It takes form as stacks of copies on shelves in the storage area known as the “book room.” Changes to the inventory require time, money and effort. Depending on the district, replacing a classic . And it would create more work for teachers who are already maxed out.

“Too many teachers, probably myself included, teach from the traditional canon,” a teacher told Stallworth and Gibbons. “We are overworked and underpaid and struggle to find the time to develop quality lessons for new books.”

The end of an era?

Esau McCauley, the author of “Reading While Black,” describes the list of classics by white authors as the “.” At least two factors suggest that its dominance over the curriculum is coming to an end.

First, the battles over which books should be taught have become more intense than ever. On the one hand, progressives like the teachers of the growing call for the inclusion of books by – and they question the status of the classics. On the other hand, conservatives have challenged or successfully banned the teaching of many new books that deal with gender and sexuality or race.

PEN America, a nonprofit organization that fights for free expression for writers, reports “” in book bans. The outcome might be a literature curriculum that more resembles the political divisions in this country. Much more than in the past, students in conservative and progressive districts might read very different books.

Second, English Language Arts education itself is changing. State standards, such as those , no longer make the teaching of literature the primary focus of English class. Instead, there is a new emphasis on “.” And while preceding generations of teachers voiced concerns about the distractions of and then , books may have an even smaller share of students’ attention in .

“We no longer live in a print-dominant, text-only world,” the National Council of Teachers of English proclaims in . The group calls for English teachers to put less emphasis on books in order to train students to use and analyze a variety of media. Accordingly, students across the country may not only have fewer books in common, but they also may be reading fewer books altogether.

Why teach literature?

Over generations, English teachers have voiced many reasons to teach books, and the canon in particular: to instill a , foster , build and cultivate . These goals have little to do with the skills emphasized by contemporary academic standards. But if literature is going to continue to be an important part of American education, it is important to talk not only about what books to teach, but the reasons why.

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