In Twelfth Night, how does the clown prove that Olivia is a fool?

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Throughout the play, Feste calls other people fools as an insult. For him, being a "fool" is a profession, but when he calls another person a fool, he means it more as we use it today, to mean "a stupid or unwise person." When he tells Olivia that she is...

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Throughout the play, Feste calls other people fools as an insult. For him, being a "fool" is a profession, but when he calls another person a fool, he means it more as we use it today, to mean "a stupid or unwise person." When he tells Olivia that she is a fool, he means that she is being unwise or acting in a nonsensical way. He shows this to be the case by demonstrating that her mourning for her brother is foolish. She mourns for the loss of her brother, but if his soul is in heaven, as she believes, then there is no reason to mourn, Feste says. Therefore, since she is mourning her brother even though he is in heaven, she is a fool. Of course, this is only true on the surface, since mourning involves a lot more than one's concern for whether the person mourned is in the afterlife—one's own regret that one will not see them again, etc.—but on the surface level, he has proved her unwise. But he doesn't really do this to make her believe she is a fool; rather, he's trying to cheer her up.

One more thing to note is the distinction between types of fools in the Renaissance. A "natural" fool was someone who was lacking in intelligence and was kept around to entertain people; Sir Toby uses Sir Andrew as a natural fool. An "artificial" fool was a professional who entertained and amused through use of his own wits. Feste is an artificial fool. So when Feste calls people fools, he is not insulting them by saying they are professional, artificial fools like him; rather, he's implying that they are natural fools, who are entertaining because they are naturally foolish.

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Feste, Lady Olivia's court fool, is allowed the classic leeway of his position to make fun of people above him in social status, even, in this case, his mistress. He is in a bit of hot water for wandering; Malvolio criticizes him in front of Olivia, so he is eager to prove that his foolery is as sharp as ever.

Why, asks Feste, should Olivia be in constant mourning for her dead brother if, in fact, he is in heaven? Does that not mean that he is in bliss? If so, then who is really the fool here? The answer, says Feste, is Olivia.

By this means of communication, a sly but comic insult which amuses his mistress, he worms his way back into her good graces.

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This encounter between Feste and his mistress, Olivia, occurs in Act I scene 5. Feste, having heard his mistress bid that the "fool" be taken away, says that Olivia should be taken away. When asked to prove that Olivia is mad, he does so by asking her about her dead brother. When asked if her brother is in hell, Olivia angrily responds that he is in heaven. Feste responds by saying he has proven that Olivia is a fool:

The more fool, madonna, to mourn for your brother's soul, being in heaven. Take away the fool, gentlemen.

This scene shows Feste's function as the court fool to Olivia: he is meant to bring amusement with his ridiculous twisting of words, and to brighten even the darkest of moments. He is a topsy-turvy figure, who with his cunning wordplays turns everything on its head and makes one thing seem to be like another. This is something that Viola recognises in her soliloquy about Feste, and this is also something that brings Feste into conflict with Malvolio, who does not appreciate Feste's humour in any sense. It is this conflict that forms such a vital element of the subplot of this play, as Feste goes on to twist the words of Malvolio to such an extent that he doubts his own sanity.

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