The Screwtape Letters

Lewis is so clever, intelligent, and insightful - it makes me sad that he was beholden to irrational beliefs that inspired him to ignore the logical conclusions of his inquiries, and sometimes even to advocate for truly monstrous ideas.

The good:

Screwtape's observations are keenest when they touch on human nature and the pleasure or misery it can bring to oneself and others. The passive-aggressiveness that can reside in “selflessness,” the danger of assuming that romantic infatuation alone can sustain a long-term relationship, and the paradoxical human need for both novelty and familiarity - these are examples of the most thought-provoking and useful passages.

The bad:

By writing from the satirical point of view of a demon, Lewis certainly brings some humor to the tale. But this also allows him to dodge the Problem of Evil and other logical gaps. From the demons' vantage, Yahweh is understandably inscrutable. But if one steps back, it's pretty disturbing how much the “loving” deity likes to mess with the heads of its followers.

In fact, I found it really shocking that Lewis, who seems genuinely interested in morality and benevolence, explicitly venerates infant death as one of the greatest goods on Earth.

And of course, he's completely a product of his time. His language is unrelentingly sexist, and his ideas don't contradict that theme.

He sometimes seems less philosophically reflective than butthurt that trendy people consider him passe. In the later “Screwtape Proposes a Toast,” he goes full Grumpy Old Man, decrying kids these days. His rant dovetails perfectly with today's “everyone getting a trophy is ruining civilization” complaints. Except that his objections go far beyond soccer trophies. He literally argues against free universal education, worrying that the “dunces” are dragging down the properly intelligent (i.e. rich enough for private school) students.

The upshot:

All in all this was worth reading because Lewis is so influential, and he does offer some very clever insights into human foibles. But it was neither as entertaining nor as intelligent as I would have expected.