ChatGPT’s Best Books of All Time: A 2023 AI Reading List Revisited

In early 2023, when ChatGPT was still a novelty to most readers, we asked it a deceptively difficult question: What are the best books of all time? Its answer was competent, recognizable, and extremely safe. Revisiting that exchange now says as much about how an AI builds a literary list as it does about the books themselves.

This article preserves the two lists produced in that original experiment. It is a snapshot, not a permanent or official ChatGPT ranking: different wording, models, and conversations can produce different answers. OpenAI also explains that the same question may yield different responses and advises readers to verify important claims. A literary ranking is subjective rather than factual, but the warning still matters—an AI’s confident tone is not evidence that its choices are neutral.

The First 10 Books ChatGPT Chose

The original response began with a reasonable caveat: “best” depends on personal taste and what a reader wants from a book. It then named ten classics that it said had significantly influenced literature and culture:

1. Pride and Prejudice by Jane Austen
2. The Great Gatsby by F. Scott Fitzgerald
3. To Kill a Mockingbird by Harper Lee
4. The Lord of the Rings by J. R. R. Tolkien
5. The Catcher in the Rye by J. D. Salinger
6. The Hobbit by J. R. R. Tolkien
7. Animal Farm by George Orwell
8. 1984 by George Orwell
9. One Hundred Years of Solitude by Gabriel García Márquez
10. Moby-Dick by Herman Melville

Our Reaction: A Good but Predictable List

There is little to object to book by book. Austen’s comedy of manners remains brilliantly readable. Fitzgerald, Lee, Salinger, and Melville are fixtures of American classrooms. Tolkien transformed modern fantasy, Orwell gave political language some of its most durable warnings, and García Márquez helped bring magical realism to an enormous international readership.

But the choices feel like a consensus assembled from other consensus lists. Eight of the ten books were originally written in English. Seven of the ten authors are men. The list doubles up on Tolkien and Orwell, using four positions on only two writers. It also leans heavily toward books commonly assigned in American and British schools.

That does not make the answer wrong. It makes the answer conventional. When asked an underspecified question, a language model tends to produce a broadly acceptable response built around recognizable patterns. “Best” quietly becomes “most likely to appear on familiar best-of lists.”

The Next 10 Books ChatGPT Added

We asked the chatbot to keep going. The second response reached further back into the traditional Western canon:

11. The Bible
12. The Iliad and The Odyssey by Homer
13. The Divine Comedy by Dante Alighieri
14. Don Quixote by Miguel de Cervantes
15. War and Peace by Leo Tolstoy
16. The Brothers Karamazov by Fyodor Dostoevsky
17. Jane Eyre by Charlotte Brontë
18. Wuthering Heights by Emily Brontë
19. The Picture of Dorian Gray by Oscar Wilde
20. Heart of Darkness by Joseph Conrad

This group makes the historical ambition clearer. It includes epic poetry, religious scripture, foundational European novels, and major nineteenth-century works. Don Quixote helped shape the modern novel; War and Peace joined private lives to sweeping history; the Brontë novels changed the possibilities of interior and romantic fiction.

Yet the omissions become even more visible. No work from East Asia, South Asia, the Middle East, or sub-Saharan Africa appears. Latin America receives one representative across all 20 selections. There are only four women authors, and none of the choices was first published after 1967. Calling this “the best books of all time” gives a global label to a mostly European and North American syllabus.

What the AI List Gets Right

• It gives new readers recognizable starting points. Nearly every title has generated decades of discussion, criticism, and adaptation.
• It spans several major forms. The answers include novels, novellas, epic poetry, fantasy, satire, and religious writing.
• It acknowledges subjectivity. The response did not pretend there was a measurable formula for literary greatness.
• It is difficult to dismiss the influence of the selections. Even readers who dislike a particular title can usually understand its cultural importance.

What the List Misses

A stronger global list would make room for books such as The Tale of Genji by Murasaki Shikibu, Things Fall Apart by Chinua Achebe, Beloved by Toni Morrison, Season of Migration to the North by Tayeb Salih, Midnight’s Children by Salman Rushdie, and The Vegetarian by Han Kang. Those are not automatic replacements or a definitive correction. They simply show how dramatically the answer changes when the prompt asks for broader geography, more women, different traditions, or more recent work.

Genre is another blind spot. Tolkien represents fantasy, but science fiction, crime, romance, horror, graphic novels, and children’s literature receive almost no attention. A list built around influence within genres would probably include a very different set of books.

How to Get Better Book Recommendations From ChatGPT

The experiment improves when the question improves. Instead of asking for the “best books,” specify what kind of list you want: 20 novels from 20 countries; classics under 300 pages; influential books by women; modern literary fiction for a reader who loves Toni Morrison; or a balanced list with no more than one title per author.

OpenAI’s own prompting guidance recommends being clear and specific, reviewing the answer, and refining the prompt. That approach turns an AI list from a verdict into a useful conversation starter.

The Verdict

ChatGPT’s original list is solid if you want a tour of famous Western classics. It is much less convincing as a universal account of the greatest books ever written. The safest way to read it is as a mirror of literary consensus: it shows which titles have been repeated so often that they become the most probable answer.

That makes the experiment interesting, even when it is predictable. For a deliberately human alternative, compare the results with our own 100 best books of all time—and then make a list that reflects the books that actually changed you.