In many ways The Pilgrim's Regress is a continuation of the themes and ideas found in Spirits in Bondage and Dymer; however, rather than continuing the spiritual floundering evident in the two earlier works, PR reflects the reality of Lewis' conversion to Christ. Written amazingly in just two weeks between August 15-29, 1932 (Lewis said in an Ocotober 29, 1932 letter to Barfield, "it spurted out so suddenly"), and published in 1933, two years after this conversion, PR is an allegorical review of Lewis' own spiritual pilgrimage as well as an often sharp-tongued attack on the spiritual landscape of contemporary England as he saw it. John, its central character, begins, like Dymer and the persona of many of the poems in SB, with a search for joy. Along the way he is attracted to many things that he mistakes for joy, but it takes a long pilgrimage before he realizes that he has been too easily satisfied with substitutes for joy rather than the real thing. In the end, he finds joy in an unexpected way.

The key to understanding the allegory of PR is found in the long note Lewis provides with the text itself. There he writes extensively on what joy means to him and how the book is intended to chart his search for joy allegorically. About allegory Lewis says its use is not intended to disguise, "but in fact all good allegory exists not to hide but to reveal; to make the inner world more palpable by giving it an imagined concrete embodiment." Readers will have to decide for themselves whether or not Lewis followed his own notion here, though even he admits that he thinks he has failed in making the allegory "work" for most readers. On the other hand, he is helpful when he states: "The book is concerned solely with Christianity as against unbelief." Any analysis on PR must be guided by this claim.

Book One: The Data

1. Who or what are John? the land of Puritania? the Landlord? the Stewards? the black hole? the Island? the brown girls?

Book Two: Thrill

1. Who is Mr. Enlightenment? What is his view of the world? How does he affect John?
2. Who is Vertue? Media? Mr. Halfway? What substitutes for joy does John accept? What causes him to reject them eventually?

Book Three: Through Darkest Zeitgeistheism

1. Who are the Clevers? How is John treated by them?
2. How is John beset by the Spirit of the Age? According to Sigismund Enlightenment, what is all human aspiration reduced to?
3. Who defeats the Spirit of the Age? How?

Book Four: Back to the Road

1. What does Reason tell John about the Landlord? his desire for the Island? about the riddles she asked? wish-fulfillment?

Book Five: The Grand Canyon

1. What is the Grand Canyon? Who is Mother Kirk? What is her story? Why don't Vertue and John accept her advice?
2. Who is Mr. Sensible? What is his philosophy of life? What does he say about Reason?

Book Six: Northward Along the Canyon

1. Who are the three pale men? How is it that they co-exist? Who are the Cruels?

Book Seven: Southward Along the Canyon

1. Why do John and Vertue become separated? What is wrong with Vertue when they reunite?
2. Who is Mr. Broad? What is his philosophy?
3. How is John aided by Contemplation?
4. Summarize the main tenets of Mr. Wisdom's philosophy.

Book Eight: At Bay

1. How does Vertue regain his sight?
2. What evidence is there that John is coming to faith?
3. Discuss the significance of the poem in Chapter Six: "Caught"
4. How does the Hermit help John? How does he explain the universal implication of John's desire for the Island?

Chapters Nine and Ten are critical.

Book Nine: Across the Canyon

1. Describe John's dream. What is he afraid of? Why?
2. How does Reason aid him? How does Mother Kirk aid him?
3. Describe John's finding the Island. What does Slikisteinsauga tell him?

Book Ten: The Regress

1. What do John and Vertue see about the world as they regress?
2. How is God's creation of Hell justified?
3. What are the dragons that John and Vertue slay?
4. Discuss the poetry of "The Regress." Is it effective? Good? Bad?

One of the best critical sources on The Pilgrim's Regress is Kathryn Lindskoog's Finding the Landlord: A Guidebook to C. S. Lewis's Pilgrim's Regress (Chicago: Cornerstone Press, 1995)