During the thirty-one years that Lewis practiced Christianity, he offered three stories—or variations on a single story, depending on the angle one wishes to take—regarding the reason for his conversation. Critically, too, the three stories overlapped and played off one another. The first, the fulfillment of his paganism and paganism, in general. The second, his regress from modernity. And, third, the persistence of joy.
One may find the second version of Lewis’s conversion in his fascinating but somewhat erratic allegory, The Pilgrim’s Regress (1933), the book that really began Lewis’s career as recognizably “the C.S. Lewis” who would soon become so famous as the world’s foremost Christian apologist. In it, Lewis fictionally traces his own autobiographical intellectual and faith journey. “On the intellectual side my own progress had been from ‘popular realism’ to Philosophical Idealism; from Idealism to Pantheism; from Pantheism to Theism; and from Theism to Christianity.” Stunningly, he wrote the entire work in two weeks while staying with Arthur Greeves in August 1932. It’s original title was: The Pilgrim’s Regress, or Pseudo-Bunyan’s Periplus: An Allegorical Apology for Christianity, Reason, and Romanticism.
Though drastically uneven in its ability to convey Lewis’s successes (and failures), The Pilgrim’s Regress possesses not a dull moment, though, in parts, it is viciously scathing toward opponents of Christianity and those Lewis dislikes. Upon writing it originally, he claimed to be mocking “Anglo Catholicism, Materialism, Sitwellism, Psychoanalysis, and T.S. Eliot.” At times, the book is gentle, and, at times, brutal, especially in its descriptions of immorality and its attacks upon ideas and persons Lewis disliked. “The sole merit I claim for this book is that it is written by one who has proved them [his opponents] all to be wrong,” he explained in 1943. “There is no room for vanity in the claim: I know them to be wrong not by intelligence but by experience, such experience as would not have come my way if my youth had been wiser, more virtuous, and less self-centered than it was.”  Lewis believed, in the interwar period, that while all of the various schools of thought hated one another, they set aside their personal dislikes for their general hatred of anything that seemed, however slight, romantic, dismissing romanticism as mere “nostalgia.”
The Pilgrim’s Regress also possesses all the strengths and weaknesses of an allegory. Some allegorical elements are obvious to the reader, while others are frustratingly obscure. Given that Lewis’s rightful claim to fame came from his ability to explain complex ideas in a way understandable by all, The Pilgrim’s Regressis a failure, though a heady one. “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,” Lewis wrote ten years after the book’s first publication, admitting his own failure to create a convincing allegory.
The story begins in Puritania, a thinly-veiled Ulster, in which the protagonist is given a list of rules. Should he not follow the rules—assuming the Landlord discovers such breaches—he will spend eternity in a “black hole full of snakes and scorpions as large as lobster.” Everyone in Puritania wears masks when performing religious ceremonies, masks that allow them to be something they are not, and to give them courage to enforce the seemingly draconian rules of the Landlord. As the protagonist, John, flees from Puritania, he meets Mr. Enlightenment (there are several claiming the title), the Clevers (the in-crowd Lewis despised in prep school), Reason, Vertue (the Stoic), Mother Kirk (the Christian Church), Mr. Neo-Angular (Wydham Lewis or T.E. Hulme?), Mr. Neo-Classical (T.S. Eliot and his authors who wrote for his journal, The Criterion), Mr. Humanist (Irving Babbitt), The Guide, and a myriad of others. In his seemingly ceaseless journeys, he visits not just Puritania (his origin), but also Claptrap, Luxuria, Thrill, Hunch, Wisdom, the Grand Canyon, Superbia, and Ignorantia. Whether the story ends on a happy or disastrous note is up to the reader, and it is equally up to the reader to decide if the entire story was real or merely a dream.
At first, the book sold poorly, and its publisher, J.M. Dent and Sons, sold the publication rights to Frank Sheed, the whirlwind behind the Catholic publishing house, Sheed and Ward. Sheed and Ward published the second and third editions of the book, but Lewis was furious at having to work with a Catholic publisher.
My other bit of literary news is that Sheed and Ward have bought the Regress from Dent. I didn’t much like having a book of mine, and especially a religious book, brought out by a Papist publisher: but as they seemed to think they could sell it, and Dents clearly couldn’t, I gave in. I have been well punished: for Sheed, without any authority from me, has put a. blurb on the inside of the jacket which says ‘This story begins in Puritania (Mr Lewis was brought up in Ulster)’—thus implying that the book is an attack on my own country and my own religion. If you ever come across any one who might be interested, explain as loudly as you can that I was not consulted and that the blurb is a damnable lie told to try to make Dublin riff-raff buy the book.
Of course, if Puritania is not Ulster, the allegory completely falls apart, and, if nothing else, Lewis’s bias against Catholics just proved Frank Sheed’s blurb to be quite true. One of Lewis’s students remembered his frustration as well: “Then Sheed and Ward took it over, and I’m not sure he was entirely happy that Sheed and Ward took it over, because Sheed and Ward were a Roman Catholic publisher, and I think Lewis, who of course came from Northern Ireland—at that time, probably would have thought it was not best to have his book put out by a Roman Catholic firm.”
Reviews, though, offered a rather nuanced view of the book. The Time Literary Supplement, for example, reported the poetry found within The Pilgrim’s Regress a grand success, evoking a holy joy. Yet, the review cautioned, “though Mr. Lewis’s parable claims to reassert romanticism, it is the romanticism of homesickness for the past not of adventure towards the future.” Jane Spence Southron, reviewing the second (Sheed and Ward) edition for The New York Times, found the book a delight, “a fresh wind blowing across arid wastes.”
 CSL, Afterword to Third Edition, Pilgrim’s Regress, 200.
 Sayer, Jack, 136.
 CSL to Guy Pocock, January 17, 1933, in CSL Collected Letters, Vol. 2: 94.
 CSL, Afterword to Third Edition, Pilgrim’s Regress, 203.
 CSL, Afterword to Third Edition, Pilgrim’s Regress, 205.
 CSL, Afterword to Third Edition, Pilgrim’s Regress, 208.
 CSL, The Pilgrim’s Regress, 5.
 One of CSL’s greatest friends and students, George Sayer, claims The Pilgrim’s Regress ends in great joy. He might very well be right. See Sayer, Jack, 137.
 CSL to Greeves, December 7, 1935, in CSL Collected Letters 2: 170.
 Interview with Harry Blamires [student of CSL’s], WCWC. Interviewer: Lyle W. Dorsett. Date: October 23, 1983. Location: Wade Center, Wheaton College.
 “Pilgrim’s Regress,” Times Literary Supplement (July 6, 1933), 456.
 Jane Spence Southron, “The Pilgrim’s Regress and Other Works of Fiction,” New York Times(December 8, 1935), pg. BR7.