The Devil’s Fear of Comedy
I've been feeling a particular kind of creative malaise lately. A shitty internal confrontation when I have to recognize that what I can produce in my humble dedicated daily hour of writing pales in comparison to what I consider "actually good writing", and the gap feels insurmountable. Most days my words feel weak, my voice inconsistent. I’m bad, it’s all bad. “But it's also fine, it's whatever” I tell myself, because I understand by now that good enough just has to be good enough to build the habit, abandon persona and adopt authenticity, develop my depth, and skillset. They say one of the ways to begin bridging the gap is by learning from masters of the craft, to read until your eyes fall out, to read with purpose and refine what you deem “good writing” and why, and “bad writing” and why.
So a few weeks ago I put aside my pile of well-intentioned self-development books and decided to dedicate my reading time to literary fiction, to approach it with a writer's lens, hoping to absorb some tricks, expand my vocabulary, and generally become gooder at words. First pick from the pile: C.S. Lewis's The Screwtape Letters and Ding! Ding! Ding! Good writing! Everybody get it.
If you're unfamiliar, the book is essentially a training manual written by a senior demon, Uncle Screwtape, for his amateur-demon nephew who's working to convert his assigned earth-human to the dark side. What emerges is a fascinating pattern: religion, human virtue, and prayer aren't the demon's primary concerns. Instead, Screwtape obsesses over the far greater threats of humility, joy, and laughter. He repeatedly warns his nephew about the dangers of letting humans experience genuine humour, which he claims threatens their evil operation because comedy promotes humility and self-awareness, which promotes connection and community.
Screwtape makes a crucial distinction that every comedic creator, and I guess every human person should take to heart; There's laughter that serves demonic purposes , this is the cruel, mocking, cynical takes that tear people down and feed superiority complexes - it’s the comedy that "others" our fellow humans. Then there's the wholesome humour that genuinely frightens demons - the kind that deflates grandiosity, reveals uncomfortable truths, and helps humans connect with their own absurd dysfunction through affection rather than shame. It’s "spiritually beneficial" comedy. The first approach harvests engagement through outrage and schadenfreude; the second builds genuine community and promotes collective healing.
We hear it constantly in the industry - that the best comedy punches up at pretension, not down at vulnerability. When you mock the powerful, the hypocritical, or the absurd (especially yourself), you're doing what Screwtape deems dangerous work. You’re helping people see themselves clearly and safely. When you punch down at the marginalized, the struggling, or the different, you're just pandering to trolls and propping yourself up on a fickle foundation. The community cultivated from that kind of connection will absolutely turn on you too. It's just a matter of time.
That being said, the humility advantage is a fine line to walk. The most demon-defying comedy helps humans recognize their own dysfunction without the messenger deteriorating their dignity along the way. For creators, this translates to a simple rule: roast yourself first, tell your story first. Self-deprecation doesn't require self-destruction to foster connection. You can admit you're flawed, spill your secrets, and do it without your audience losing respect or walking away with a pity hangover. Approach it with confidence, and you grant your audience permission to be human too.
Screwtape inevitably connects this to joy of course, they go hand-in-hand, though that's not always true for comedic creators. He describes joy as "the most difficult thing to corrupt" and instructs his nephew to prevent humans from experiencing it at all costs. Here's another crucial distinction: joy is not pleasure. Pleasure is the dopamine trap, it’s delivered from external, temporary, hollow returns that demand increasingly more stimulation. Joy comes from within, lasts longer, and grows stronger when shared with community. Comedy created from genuine joy carries significantly different energy than content desperately manufactured for attention or control.
Joy-driven creators aren't constantly chasing trends because they're not trying to escape themselves. They're not regurgitating hot takes or desperately inserting themselves into conversations without meaningful contributions just to occupy space. They're sharing something they genuinely find delightful, silly, or real and that authenticity is magnetic in ways that manufactured vitriol, however viral, can never match.
So I'm curious: does your sense of humour serve Screwtape's agenda? Does your content depend on cruelty, superiority, or cynicism? Is it separating people and feeding egos? Or does it build community, reveal truth with kindness, and share genuine delight?
Disclaimer: this isn't about being preachy or sanitized. It's about choosing connection over division, shared humanity over manufactured outrage.
You're not fucking interesting just because you're angry. You're not a philosopher just because you're recklessly provocative.
Humour and joy aren't just "nice-to-haves." In an industry that rewards narcissism and punishes vulnerability, genuine humour keeps you grounded by reminding you that everyone - including you, including me - is a beautiful fucking mess. Joy helps us transcend the mundane and celebrate everyday absurdities together.
Don't listen to the demons whispering that you need to be more extreme, more controversial, more willing to sacrifice your integrity for scraps of attention. Serve your audience's highest self instead of their lowest impulses. Cultivate a community that takes collective delight in our shared dysfunction. I truly believe when we intentionally choose joy over outrage, humility over superiority, and connection over division, we're not just creating better content, we're creating the kind of healing we all desperately desire.