What does Aristotle mean by "pleasure proper to tragedy" in Poetics?

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By "pleasure proper to tragedy," Aristotle means the moral emotions that it elicits. Tragedy, he writes in his Poetics, should excite in audiences the emotions of "pity and fear."

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When Aristotle talks of the pleasures proper to tragedy, he is referring to the pity and fear elicited by a tragic play. On the face of it, it may seem somewhat strange to regard pity and fear as pleasurable experiences. Surely, we might think, they are anything but.

According to Aristotle, however, fear and pity are pleasurable emotions because our experience of them brings about their purgation. This is a process that he calls catharsis, which can be defined as the purification of the soul through pity and fear—a kind of ceremonial purification.

When we experience these emotions while watching the performance of a tragedy, our souls are being purged of impurities, just as someone's body can be purged of impurities by the administering of medicine by a doctor. In both cases, we feel pleasure at being purified; what was damaging us from the inside has now been removed.

To be sure, there's nothing wrong with having such emotions; everyone has them to a certain degree. But in excess, they can be harmful, and so it's necessary from time to time to purge them from our souls. They need to find a healthy outlet, and what better outlet can there be than a performance of a tragic play?

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Aristotle, speaking of tragedy in his Poetics, places the pleasure it gives us within a moral context. It is not, for instance, the proper purpose of tragedy simply to sadistically enjoy watching others suffer. It is also not morally proper to respond to to tragedy with schadenfreude, the quality of superiority, or with shallow flippancy.

Aristotle states that tragedy should properly raise "pity and fear" in an audience. By pity, Aristotle means empathy. A good tragedy, such as Oedipus Rex, causes us to identify with and feel the suffering of the protagonist, a well-meaning person with a tragic flaw. We don't feel superior or indifferent to Oedipus, a leader who cares deeply about his people in a time of pandemic or plague. Instead, we identify with the anguish he is going through as his world unravels. Likewise, a good tragedy raises our fear of repeating the moral transgression that led to the tragic outcomes in the play. Using Oedipus Rex as an example once again, the play sends a strong message to its audiences not to transgress against the will of the gods: don't think you, a mere individual, can outsmart the laws of the universe. Oedipus's fate helps to drive that message home.

Writers need to keep in mind, Aristotle advises, the higher purpose of art, which is to morally elevate the public.

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Poetics by Aristotle: we must not demand of Tragedy any and every kind of pleasure, but only that which is proper to it ....

In Aristotle's Ethics (VII.11-14 and X.1-5), he describes pleasure as (1) necessary to human life, (2) not solely derived from the senses, and (3) the outgrowth or product of excellent activity, and (4) not something to be sought deliberately as it is a product not an originating cause. Having said this, compare Aristotle's idea of pleasure to our usual contemporary understanding of pleasure:

American Heritage Dictionary
pleasure:
1. The state or feeling of being pleased or gratified.
2. A source of enjoyment or delight

While there is nothing here to contradict Aristotle, our contemporary understanding of pleasure is devoid of the philosophical element and renders it more akin to an emotion like joy or happiness.

When Aristotle uses pleasure in reference to tragedy, he is speaking in philosophical terms and not according to our current concept. Remembering that pleasure comes as the product of excellent activity that is fulfilled without hindrance or opposition, consider viewing a tragedy as an activity.

Viewing a Greek tragedy might well be considered an excellent activity as they were excellently crafted with high, elevated diction and objectives. Therefore, by definition, a Greek tragedy may produce pleasure. Further, a tragedy has qualities particular to it that are equally out of accord with comedy and monstrousness. The sensation duly associated with tragedy is to be that of the terrible. The appropriate product of pleasure would, as Aristotle states, then be pity and fear. In other words, if one feels pity for the characters, particularly the tragic hero, if one feels fear for the heroes ultimate end, one has engaged in an excellent activity that has produced pleasure proper to tragedy.

Those who employ spectacular means to create a sense not of the terrible but only of the monstrous, are strangers to the purpose of Tragedy; for we must not demand of Tragedy any and every kind of pleasure, but only that which is proper to it. And since the pleasure which the poet should afford is that which comes from pity and fear through imitation, it is evident that this quality must be impressed upon the incidents. (Poetics by Aristotle)

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What do you think Aristotle means by "pleasure proper to tragedy?"

The "pleasure" of which Aristotle speaks is more of an appreciation of the beauty of a work of art that embodies tragedy.  I think that Aristotle is bringing out the idea that art, while it can depict the worst of consciousness, can be beautiful in this depiction.  For example, art can display the most painful of conditions but do so in a manner whereby one can only express appreciation of it.  When I speak with students about "favorite movies," I always indicate "Schindler's List" or "Sophie's Choice."  Almost a patterned response that the kids have upon hearing this is, "That's so depressing!  How could you like that!"  I think that Aristotle's understanding of "pleasure" might be evident here.  When a work embodies the principles that Aristotle attributes must be contained in an effective work, it is in this light that tragedy can contain a level of "pleasure" for the work has impacted the audience on both an emotional level of fully understanding the tragic predicament of the protagonist, and has done so in an aesthetic light where its construction has captured the audience's imagination.

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