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• When Screwtape gets worked up about the difference between Heaven and Hell, to the degree that he involuntary takes the form of a large centipede. It becomes even funnier when read by John Cleese, who had to pick bits of studio from between his teeth after that particular take.
• In the play version, Screwtape points out that famous people are a "good" influence, since they're always changing their minds...then tilts the book he's reading to reveal that it's a biography of Madonna. Cue "Material Girl" playing during the next set change.
• The events and letter that occur when Screwtape discovers that dear nephew Wormwood has been passing his letters and criticisms along to Hell's secret police. The frantic ass-covering that Screwtape engages in is hilarious.