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.