* When Screwtape gets worked up about the difference between Heaven and Hell, to the degree that he [[InvoluntaryShapeshifting involuntarily takes the form of a large centipede]]. It becomes even funnier when read by Creator/JohnCleese and ESPECIALLY Creator/AndySerkis, who both had to [[ChewingTheScenery pick bits of studio from between their teeth]] after that particular take.
* Screwtape's rants about the girlfriend Wormwood's target has--she's a good Christian and ''happens'' to be a charming and sexy vivacious young woman who's also "the sort of creature who'd [[AnythingButThat find ME funny!]]"
* 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 {{Music/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.
* Screwtape telling Wormwood how this secret God's keeping called "love" was the cause of the falling-out between Him and Satan. According to [[UnreliableNarrator Screwtape]], God's failure to trust Satan with the secret caused him to storm out so suddenly that it led to the "ridiculous" story about him being expelled from Heaven.
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