These recommendations are genuine and based on my own reading, with the exception of List 3. Most of the contents of List 3 were supplied to me once by the brilliant Dale Rhodes of Enneagram Portland. The autobiographies/memoirs are recommended by Michael Naylor of Enneagram Maine.
1. Books that are directly about the Enneagram
The Essential Enneagram: The Definitive Personality Test and Self-Discovery Guide, by David Daniels and Virginia Price. I know of no better book on typing.
The Enneagram Made Easy: Discover the 9 Types of People, by Renee Baron and Elizabeth Wagele. One of the best entry-level Enneagram books. Wonderful humour and illustrations.
The Wisdom of the Enneagram: The Complete Guide to Psychological and Spiritual Growth for the Nine Personality Types, by Don Riso and Russ Hudson. I do not like the type descriptions in this book, but it is a powerful guide to inner work with the Enneagram.
Keys to the Enneagram, by A. H. Almaas. Important perspective from A. H. Almaas linking each type with an ego ideal and core essence quality. Explains how to inquire into your relationship with each type’s essence quality.
Facets of Unity, by A. H. Almaas. The most detailed breakdown on the Holy Ideas anywhere. Not for the beginner student.
Aspects of You, by Cicci Lyckow Bäckman. Accessibly written book from an Enneagram teacher who is less interested in typing and more interested in the inner work, and correcting common mistakes to do with the Centers and Instincts.
The Enneagram Guide to Waking Up, by Beatrice Chestnut and Uranio Paes. Excellent practical growth book from a beloved Enneagram duo, suitable for beginners. I found the zombie metaphor to be very apt!
The Complete Enneagram, by Beatrice Chestnut. A coach’s bible. This is most well known for setting out Beatrice’s versions of the subtypes but it is also great on the self-observation practices for each type.
Nine Gateways to Presence, Russ Hudson/Soundstrue. A beautiful listen (rather than read) and a few developments/finer points here from his seminal book with Don Riso, Wisdom of the Enneagram.
The Instinctual Drives and the Enneagram, by John Luckovich. Useful on the instincts.
The Enneagram of Passions and Virtues and The Spiritual Dimension of the Enneagram, by Sandra Maitri. Everyone loves Sandra’s beautiful books. This is the Enneagram from the perspective of the Diamond Approach spiritual path.
Character & Neurosis, by Claudio Naranjo. Very psychological. Brilliant on the psychological traits of each type from the core developer of the Enneagram.
Personality Types, by Don Riso and Russ Hudson. Really detailed on the Levels of Development, and the Appendix at the back containing the Core Dynamics is powerful.
Enneagram Transformations, by Don Riso. Excellent on affirmations/growth practices for each type.
The Enneagram Triads, by Dick Wright. An interesting, and I think helpful alternative perspective on the three triads.
2. Books covering aspects of inner transformation
Diving in the Inner Ocean: An Introduction to Personal Transformation Through Diamond Inquiry, by Dom Liber. Dominic’s simply written book teaches you how to practice inquiring into your experience in a way that enables you to understand what is going on with you more deeply.
Soul Without Shame: A Guide to Liberating Yourself from the Judge Within, by Byron Brown. This is actually a book about how to work with the Inner Critic, the internal structure that we all have which is a large obstacle to progressing in inner transformation.
On Becoming an Alchemist: A Guide for the Modern Magician, by Catherine MacCoun. I found this book via Buddhist teacher Susan Piver and I am so happy I did. I think it contains important truths and guidance about the process of inner transformation.
Spiritual Bypassing: When Spirituality Disconnects Us from What Really Matters, by Robert Masters. A fiery little book addressing an important concept for anyone engaged in their development to be aware of.
3. Memoirs, autobiographies, and works of fiction that depict type themes
A Man Called Ove, by Fredrik Backman. Enneagram type 1 is represented by angry old man and curmudgeon, Ove.
Cold Comfort Farm, by Stella Gibbons. Enneagram type 2 Flora loves nothing better than to organise other people.
Black Narcissus, by Rumer Godden. Enneagram type 3 Mr Dean’s charm and candour are disconcerting to some well-intentioned but misguided nuns.
Life After Death, by Damien Echols. Memoir from Enneagram type 4 Echols, falsely convicted of committing three murders.
Hedda Gabler, by Henrik Ibsen. Enneagram type 4 Hedda Hedda Gabler marries dull George Tesman and foresees a life of middle-class tedium stretching ahead.
Into the Wild, by Jon Krakauer. A young man from a well-to-do family hitchhikes to Alaska and walks alone into the wilderness – the unforgettable story of Christopher Johnson McCandless, aka Alexander Supertramp, probably an Enneagram 5.
Divergent, by Veronika Roth. The bestselling Dystopian series highlights themes of Enneagram type 6.
Robin, by Dave Itzkoff. The late Robin Williams must be one of the most cited exemplars of Enneagram type 7.
The Mayor of Castro Street, by Randy Shilts. Enneagram type 7 Harvey Milk’s personal and political life is a story of the consolidation of gay power and gay hope.
A Raisin in the Sun, by Lorraine Hansberry. Enneagram type 7 themes ring through Lorraine Hansberry’s award-winning drama about the hopes and aspirations of a struggling, working-class family living on the South Side of Chicago.
Ali: A Life, by Jonathan Eig. Autobiography of a famous Enneagram type 8.
Mother California: A Story of Redemption Behind Bars, by Kenneth Hartman. The memoir of convicted murderer and Enneagram type 8 Kenneth Hartman, whose growing self-awareness enables him to understand his crime and achieve redemption.
My Ántonia, by Willa Cather. Enneagram type 8 is brought to life through an orphaned boy from Virginia, Jim Burden.
The Sun Does Shine, by Anthony Ray Hinton. The powerful story of an Enneagram type 9 on Death Row.
The Stone Diaries, by Carol Shields. The moving fictionalized autobiography of Enneagram type 9 Daisy Goodwill Flett, an everywoman reflecting on an unconventional life.