Jonathan Swift and C. S. Lewis had extraordinary similarities in their lives up to their respective writings of Tale of A Tub and The Screwtape Letters. Beyond the biographical parallels, there were great similarities in the religious, historical, and political contexts surrounding the two works, even though they were published 237 years apart. These facts have been ignored by scholars, yet more important than the similitude is what Swift and Lewis did differently in spite of it. These differences represent deliberate choices each author made and provide greater insights about them and these seminal works. Both of these brilliant men became convinced that their societies needed a rebirth of spirituality and chose highly creative religious satire to convey their respective messages and “laugh us into religion.”