The Ben Shapiro Show: Book Club – C.S. Lewis’ The Screwtape Letters

Episode Date: December 22, 2025
Host: Ben Shapiro
Theme: An in-depth analysis and discussion of C.S. Lewis’ The Screwtape Letters, exploring its theological, philosophical, and cultural insights; reflections on the nature of evil, temptation, faith, and society.

Episode Overview

In this Christmas Book Club edition, Ben Shapiro presents a deep dive into C.S. Lewis’s The Screwtape Letters. Framed as a series of letters from the demon Screwtape to his nephew Wormwood, the book uses satire, theology, and keen insight into human foibles to explore how individuals are tempted and how faith can be challenged or strengthened. Shapiro analyzes Lewis’s major themes, extracts contemporary relevance from the 1942 classic, and answers listener questions, weaving in his own Jewish perspective alongside Christian thought.

Key Discussion Points and Insights

1. The Nature & Structure of The Screwtape Letters

• Lewis uses a fictional, epistolary format to satirize and seriously analyze human temptation.
• Shapiro: “Screwtape Letters is a fictional encapsulation of much of C.S. Lewis's other work… It is a spectacularly good book. One of the beautiful things about Screwtape Letters is it is a fictional encapsulation of much of C.S. lewis's other work.” (02:07)
• Lewis wrote the book with ease but little enjoyment, describing the process as spiritually taxing.

2. Humor as a Weapon Against Evil

• Lewis contends, and Shapiro agrees, that mockery and laughter are powerful tools for combating evil:
  • “Mocking evil is a great way of dismissing evil, because that's what mockery essentially is.” (04:20)
• Quotes Luther (“The best way to drive out the devil… is to jeer and flout him. For he cannot bear scorn.”) and More (“The Devil...cannot endure to be mocked”).

3. Materialism and “The Real World”

• One of Satan’s best weapons, according to Lewis, is the secular focus on the material and immediate—what is considered “real life.”
• Shapiro, quoting Screwtape: “Teach him to call it real life. Don't let him ask what he means by real.” (08:09)
• Modern technology and the age of the Internet reinforce a focus on the now and superficiality, diminishing spiritual introspection.

4. The Danger of Living in the Future and Neglecting the Present

• Screwtape urges fixation on the future, robbing people of spiritual mindfulness in the present.
• Shapiro, echoing Lewis: “If you're thinking about the future, then you're not thinking about the spiritual consequences of the things you do in the here and now.” (09:47)

5. Manipulation of Feelings & Emotions

• Screwtape exploits emotional ups and downs to discourage spiritual discipline.
• Searching persistently for inspiration in religious practice can lead to abandonment of duty when the “feeling” disappears.
• Shapiro: “If you focus in on the feeling, when the feeling goes short, you stop doing the duty. If you focus in on the duty, then eventually you come to feeling.” (11:29)

6. Grayness, Despair, and Everyday Temptations

• Temptation often appears not as dramatic evil but as day-to-day “grayness,” malaise, or bland distraction—resonant with modern digital culture.
• Shapiro, quoting Lewis: “It does not matter how small the sins are, provided that their cumulative effect is to edge the man away from the light and out into the nothing.” (12:34)
• Over time, numbness to both sin and virtue is spiritually dangerous.

7. Sex, Art, and the Unrealistic Pursuit of Desire

• Lewis critiques the sexualization and artificial standards set by popular art/media—analogous to today’s internet pornography and social media.
• Shapiro: “That is the greatest description of Internet porn that has ever been written... C.S. lewis is writing this in 1942.” (15:13)
• Human nature is constant; only cultural expectations and technologies change.

8. Human Relationships: Miscommunication, Marriage, and Love

• Lewis details how everyday slights and miscommunications drive wedges between people.
• On “unselfishness”:
  • "A woman means by unselfishness, chiefly taking trouble for others. A man means not giving trouble to others." (18:24)
• The family is seen as a bulwark against atomizing materialism—but the definition of love has shifted from duty to subjective feeling, weakening marriage.

9. Erosion of Duty and the Rise of Self-Centeredness

• Modern “love is love” slogans detach love from obligation, draining traditional structures of meaning and stability.
• Shapiro: “Love in the traditional sense meant duty. Love in the traditional sense meant familial relations between man, woman and children. If you redefine love as that subjective feeling within you, then love is love, I suppose, is true. The problem is that is a complete redefinition.” (20:37)

10. Individual vs. Collective Benevolence

• Screwtape encourages people to be harsh to their immediate neighbors but profess benevolence toward “mankind,” resulting in hypocrisy.
• Shapiro: “You can do some pretty terrible things to your neighbors…when you start to think that the human species is filled with joy and wonder, but the individuals who live next door to you are the worst people in the entire world.” (21:12)

11. Human (Mis)Understanding of the Divine

• Our images of God are always inadequate; frustration with unanswered prayer can stem from misunderstanding omnipotence and free will.
• Materialist “magic” (belief in impersonal ‘forces’ but not the spirit) is identified as a new form of idolatry.

12. Moderation as a Tool of the Devil

• “A moderated religion is as good for us as no religion at all, and more amusing.” (24:11)
• True devotion integrates faith into all of life, not just relegating it to church or home.

13. Courage & the Form of Virtue

• Acting in accordance with higher will—especially when it requires courage—is pictured as the test and fulfillment of virtue.

14. Faith, Reason, and Emotion

• Faith transcends reason and emotion, but is only accessible with “openness” and spiritual preparation.
• Shapiro: “Belief will come when the necessary preparation has been done…Do the things that dutiful people do. Do the things that faithful people do. And faith will come upon you.” (31:00)

Notable Quotes & Memorable Moments

• On Humor:
  • “The Devil, the proud spirit, cannot endure to be mocked.” — Thomas More, cited by Shapiro (03:37)
• On Evil’s Weapons:
  • “The chief ally of Screwtape is the material world because people desire not to think of God.” (08:55)
• On Duty:
  • “If you focus on the feeling, when the feeling goes, you stop doing the duty. If you focus on the duty, eventually you come to feeling.” (11:29)
• On Modern Culture:
  • “You spend all day on social media, consuming your time with absolute stupidities. You don't feel anything good about it. It just feels like bleh.” (12:31)
• On Porn and Unrealistic Desire:
  • “Human nature does not change. Human nature is the same as it was thousands of years ago.” (16:54)
• On Love and Marriage:
  • “If you redefine love as that subjective feeling within you, then love is love, I suppose, is true. The problem is that is a complete redefinition.” (20:37)
• On Religion in Modern Life:
  • “A moderated religion is as good for us as no religion at all, and more amusing.” (24:11)
• On Faith and Preparation:
  • “Do the things that dutiful people do. Do the things that faithful people do. And faith will come upon you.” (31:00)

Timestamps of Significant Segments

• [01:25–03:00] – Introduction and overview of The Screwtape Letters
• [03:00–06:00] – C.S. Lewis’s humor, criticisms, and approach; the role of mocking evil
• [06:00–09:45] – “The real world” as a tool of temptation; modern distractions
• [09:45–11:29] – Emotional manipulation, spiritual discipline, and the cycle of enthusiasm/disappointment
• [12:31–14:55] – Grayness, malaise, Internet age, and banality of temptation
• [14:55–18:35] – Pop culture, sexuality, human nature, marriage, and duty
• [18:35–22:27] – Miscommunication, relationships, love, and the family
• [22:27–24:11] – Human misunderstanding of God, moderation in religion, and acting with courage
• [24:11–27:51] – Listener questions: demonic influence in society; resurgence of religion; faith, emotion, and reason
• [27:51–34:37] – Q&A on faith, temptation, humility; TikTok/Internet as “grayness”; humor as a weapon
• [34:37–47:20] – On humility, humor, audience, Screwtape’s speech, gender critiques, evil, and externalizing temptation
• [47:20–57:14] – Additional listener Q&A: angels, temptation, democracy, society, Christological trilemma, Sabbath, and moderation

Listener Q&A Highlights

• Is there a resurgence of religiosity?
  • Shapiro predicts a coming religious revival, possibly linked to social/economic crises.
• Role of humility in Judaism vs. Christianity?
  • Shapiro notes humility is central in both, illustrated in the example of Moses.
• Humor: disarming vice or virtue?
  • Both—humor has power to ridicule sin but is often used today to attack virtue.
• Demons and spiritual evil: belief or metaphor?
  • Shapiro leans rationalist: evil can be personified for narrative purposes, but is often better understood as a force, not a literal being.
• Faith: is it reason or emotion?
  • Faith transcends both; it’s about openness and spiritual preparation rather than mere logic or feeling.
• Society and democracy:
  • Over-egalitarianism and envy can stifle excellence and lead potentially toward tyranny—a warning Lewis saw as prophetic.

Conclusion

Ben Shapiro’s analysis of The Screwtape Letters underscores its enduring relevance, satirical brilliance, and theological depth. Shapiro connects Lewis’s 1942 insights to 21st-century malaise and culture wars, emphasizing the need to recognize and resist “grayness,” narcissism, and materialism. He highlights the importance of humor as a shield against evil, the dangers of reducing love and duty to fleeting feeling, and the spiritual urgency of humility and discipline. The episode closes with hope: even as society faces new and old temptations, the guidance of thinkers like Lewis provides a framework for spiritual resilience.

For listeners seeking rich, actionable insight on faith, culture, evil, and human nature, this Book Club edition is a must.