Screwtape is especially fond of humor as a way of leading an otherwise good soul astray. “Humour is for them the all-consoling and (mark this) the all-excusing, grace of life. Hence it is invaluable as a means of destroying shame. If a man simply lets others pay for him, he is ‘mean;’ if he boasts of it in a jocular manner and twits his fellows with having been scored off, he is no longer ‘mean’ but a comical fellow. Mere cowardice is shameful; cowardice boasted of with humourous exaggerations and grotesque gestures can be passed off as funny. Cruelty is shameful—unless the cruel man can represent it as a practical joke” (55).

The boasting coward reminds one of the great Shakespearean character Falstaff, who embodied this type so well. This is one of the instances where Screwtape’s distorted views of human behavior seem to have a certain wisdom. Making a joke of something often does excuse actions that would otherwise be unacceptable.  

In Chapter 13, Screwtape reacts to the young man’s having a sense of divine presence using the symbol of a cloud. The cloud is an ancient symbol of the presence of God, which is found in the Old Testament of the Bible.