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The Pilgrim's Regress by C.S. Lewis
4.0

Ten years on, Lewis wrote an apology (think explanation or defense, not remorse) for the ways in which he had written The Pilgrim's Regress. In it, he mentions that perhaps the allegory is somewhat obscured by his strange path to Christianity. Anyone familiar with his story knows that he was both a passionate romantic thinker and a trained concrete thinker. These two elements bleed out in various combinations in everything he wrote. In The Pilgrim's Regress, he riffs on Bunyan (and perhaps Dante and Spencer) to explore the recent path his own life has taken among all the philosophies, zeitgeist, and political schools of history, landing at last upon Christianity and, really, personally knowing Jesus, as the only option by which his deepest fantasies and greatest longings could find a resolution that kept him desirous for more.

Like The Pilgrim's Progress, Regress is an allegory about a man with a longing who goes on a journey. As a boy, the romantic John is told about the Landlord who owns the land and makes endless rules and punishes any tenants who do not follow every rule all the time by throwing them into the black pit. After trying to keep track of the rules and continuously failing, John grows to despise the Landlord. At the same time, he is becoming obsessed with the vision of a glorious romantic island he sometimes sees. The island becomes an obsession, a symbol of untold bliss. As he searches for it in adolescence, he is waylaid by other simpler desires for brown girls (Lewis uses ghostly white people in a stark landscape to symbolize over-intellectualize and austere thinking and dark and brown skin in swampy and verdant terrain to symbolize spiritual and mystical attitudes) who come to him in his longing and distract him with small pleasures. Finally, John decides he is done with the Landlord and sets off in search of the island of his dreams and fantasies.

From here, John meets dozens of allegorical characters in all sorts of cities and landscapes. He explores some version of nearly every mindset humanity has recorded. He comes across the ancient Greek philosophies, the current art schools, the various versions of enlightenment thinking, and even the growing post-industrial movement toward Communism. He meets with all sorts of combinations of religious and secular perspectives on history and humanity, each proving to be highly deficient if not downright malignant. Along the way, John to romantic meets and befriends a man called Vertue, a puritanical sort who holds to his own principles alone. In their continued journey toward the Landlord's holdings, they become balancing opposites. While John is a romantic thinker drawn by passions like the darker people from the swamps to the south, Vertue is a man of sheer principle, drawn by ideals like the ghostly people of the barren places. Eventually, they will both be called to die to themselves and reconcile to the perspectives of the other.

I always find allegories to be somewhat distracting at their best. I cannot help but try to decypher every sentence. Even so, this book gives a more juvenile and therefore more expansive and opinionated array of Lewis perspectives than he typically offered in later works. Perhaps due to age, experience, wisdom, or all of the above, Lewis tends to breeze over nuanced stances in his later works. As a man trying to encourage all men to become Christians and encourage all Christians to find unity, he created a space where Baptists and Catholics could come together, where passionate romantics and calculating logicians could see common ground. While he argues for the same here, he spends a great deal of time exploring the promises of various movements throughout history and knocking each one down in a way that is as systematic as an allegory can ever be.