Rather than descend once more among men, Zarathustra ascends to the highest mountain and waits there for people to come to him.
Sitting outside his cave, Zarathustra is joined by the soothsayer from Part II. He tells Zarathustra that he must confront his final sin: pity. Zarathustra hears a cry of distress that he assumes comes from "the higher man," and so goes in search of him.
On his search, Zarathustra encounters two kings on the road who are driving an ass. They have abandoned their kingdoms, as they have been made nauseous by the "good society" of mediocre people who are eager only to please and to enjoy small pleasures. The kings are delighted when Zarathustra tells them he is searching for the higher man. Zarathustra directs them to his cave and invites them to wait for him there.
Next, Zarathustra literally stumbles upon a man lying down in a swamp, trying to attract leeches to his arm. He represents "the conscientious in spirit," one who wishes to free himself from (or "suck away") all the prejudices and assumptions that underlie his thinking. As with the kings, Zarathustra invites him to wait in his cave, and then continues his journey.
Zarathustra encounters a magician writhing on the ground, tortured by a thought. After a while, Zarathustra becomes angry and accuses him of counterfeiting. The magician confesses, saying he was pretending to be an "ascetic of the spirit" in an effort to test Zarathustra. Zarathustra points out that he wasn't totally pretending—that he is, in some senses, an ascetic. The magician wants to convince others that he is a great man, but he knows himself that he is not great. Zarathustra admires the magician for wanting to be great and for admitting that he is not. As with the others, he directs the magician to his cave and then continues on his way.
Zarathustra encounters the last pope, who is mourning the fact that God is dead, and who seeks out Zarathustra as the most pious of all those who do not believe in God. He tells how God died from pitying humankind too much. Zarathustra criticizes God for having made us so poorly and then punishing us for being unable to do his bidding. The pope is impressed with Zarathustra, and Zarathustra directs him to his cave.
Zarathustra enters a valley where no animals live and encounters the "ugliest man"—the man who killed God. Though he is momentarily stunned by pity, Zarathustra overcomes his pity and returns to his senses. The great pity people feel for the ugliest man's suffering offends his sense of shame. He killed God because God could see everything and know everything about him, and most of all because God felt pity. As with the others, Zarathustra directs the ugliest man to his cave.
Zarathustra encounters a voluntary beggar, who was once rich, but who became sick of rich people and so chose to be poor. He found the poor just as nauseating as the rich, however, and so he has come to sit among cows, hoping to learn from them how to chew the cud. Zarathustra invites him to go to his cave.
Zarathustra finds himself pursued by his own shadow. His shadow has followed Zarathustra everywhere and has been bold in its pursuit of truth and knowledge. Now the shadow finds itself lost and without a goal. Zarathustra directs the shadow to his cave and then continues on his way without his shadow.
Each of the men Zarathustra encounters has something of the spirit of the overman for which Zarathustra longs, but each one also falls short in some important respect. Kaufmann is astute in noting that each of the characters also represents a kind of caricature of Nietzsche himself.
The soothsayer, in Part II, predicted a heightened state of nihilism, a state that, Nietzsche might claim, we have attained today, one hundred years after Nietzsche's death. The soothsayer encourages Zarathustra's search for the higher man, suggesting that soon people will come up to Zarathustra's level. On the other hand, in his melancholy, he suggests that happiness is no longer possible. The soothsayer may represent the negative moods that Nietzsche himself often fell into: he has all the right ideals, but finds it easier to predict the worst than to aim for the best.
The two kings are of noble heritage, and they are also fed up with the superficiality of human society. They have given up their comforts and riches in order to embark on the difficult journey of seeking the higher man. Nietzsche, like a king, might have enjoyed a university pension and nursed his illness, but, instead, he abandoned all comforts in favor of his constant writing and thinking. When the kings encounter Zarathustra, they become overly worshipful, suggesting that they might be willing to stop short at finding the higher man, and not actually become overmen themselves.
In "The Leech," the man who is conscientious in spirit and who is attracting leeches, represents Nietzsche's ideal of a good philosopher. Rather than try to build upon and try to justify assumptions and prejudices that he never questions, this man wants all dogmatism to be sucked away from him. However, he has only managed to attract leeches to himself: he has freed his spirit from earlier prejudices, but he has not been able to go farther to create something new of his own.
The magician's counterfeiting as an "ascetic of the spirit"—one who torments himself with his own thoughts—is meant to represent philosophy. Nietzsche claims that philosophy was able to claim its own ground only by wearing the "mask" of the ascetic priest, by pretending, like a priest, to be a serious keeper of deep mysteries. In truth, philosophers are pranksters and light in spirit, according to Nietzsche. Like a philosopher, the magician is aware that he has not yet become an overman, and so maintains the mask of an ascetic. While he is not yet perfect, Zarathustra admires his desire to become great and his humility in admitting that he is not yet great.
The suggestion that God died out of pity is the culmination of Nietzsche's critique of pity. The God of the Old Testament is a vengeful lawgiver, but in the New Testament he is portrayed as a God who loves and pities humans. The amount of pity necessary to empathize with the suffering of all humanity is so great that not even a God could bear it. While the last pope is keen and conscientious of spirit, he also longs for a God, for absolutes.
The ugliest man has the nobility and sense of shame to resent all the pity people feel for his ugliness. In particular, he comes to see God as a voyeur who, in pitying, exposes everything that is pitiable about him. While there is a great deal that is unattractive and unpleasant about this ugliest man, Zarathustra admires his revilement of pity. Nietzsche was constantly ill and suffering, and he too probably received all kinds of unwanted pity that he grew to resent.
The voluntary beggar, like the kings, has been made nauseous by the pretenses and prejudices of common society. His desire to learn to "chew the cud" represents his interest in learning how to think carefully over matters, and to re-think them continually. Nietzsche often criticized his age for reading and thinking too quickly, and for not taking in anything important. However, like a cow, this beggar can only ruminate, and does not have a creative spirit.
Zarathustra's shadow displays the virtue of having searched long and unrelentingly for truth and knowledge, but now it has become discouraged that its search is in vain. While the shadow is a noble seeker, it does not have the stamina to continue the search. Also, it is never going under its own steam, but is always only following Zarathustra's lead. In order to become an overman, one must blaze one's own trail.