How does festes try to make Malvolio think he's crazy?
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To convince Malvolio that he is insane, Feste tosses about a few paradoxes, and contradicts some of the things that Malvolio knows to be true. Feste begins by asking Malvolio if it is light or dark where he is imprisoned; Malvolio answers that it is indeed dark, and Feste counters him by swearing that there are "bay windows transparent as barricadoes" and "lustrous as ebony" (IV.ii.37). By barricadoes, Feste means "barricades," which are not at all transparent, and ebony is dark and black, rather than light; these statements are meant to contradict what Malvolio perceives, but also to confuse him through the paradox inherent in the statements. Feste then examines him as to his belief in Pythagoras' theory of souls, and threatens to leave Malvolio when Malvolio says he does not believe in it. It would be odd for a Christian parson to believe that souls inhabit other bodies after death, rather than believing the traditional Christian idea, that souls go to heaven; however, Malvolio does not pick up on this key fact, and does not realize that Sir Topaz is really Feste in disguise.
Continuing his efforts, Feste upsets Malvolio by telling him that he is "more puzzled than Egyptians in their fog," referring to one of the plagues of Egypt in the Bible, which was a heavy fog of darkness that stayed for three days (IV.ii.45). Malvolio tries to reinforce his statement that the place where he is is dark, reasoning that "this house is as dark as ignorance, though ignorance were as dark as hell" (IV.ii.46-7). His attempt to qualify his perceptions through this simile shows how stubborn he is, and how difficult a time Feste and company will have if they want to drive Malvolio truly mad.
Feste addresses Malvolio as himself as well; but to Malvolio's calls of "fool," Feste merely taunts him with a song that rubs in Malvolio's situation, of being in love with a woman who only cares for someone else. Malvolio's cries fall flat with Feste, who acts the part of a fool, but has been displayed as someone who is rather wise; it is ironic that Malvolio would call Feste a fool, since Malvolio has acted more of a fool than Feste usually does