The article is devoted to one of the most popular heroes of Cynic literature, namely, Heracles, a figure that is, perhaps, the most contradictory and paradoxical in Greek mythology. On the one hand, antiquity knows him as the hero of the famous twelve labors, a theomachist hero, however, on the other hand, in Aristophanes' comedies he presents as a thievish glutton and swindler, and in Euripides' tragedy Herakles - as a mad hero. In our attempt to answer the question of what makes Hercules one of the protagonists of Cynic literature, we turn to the origins of the Cynic tradition - Antisthenes, who, according to Diogenes Laertius, was the author of three works about Heracles («The Greater Heracles, or Of Strength»; «Heracles, or Midas»; «Heracles, or Of Wisdom or Strength»). Based on the fragments that have survived to this day, as well as on the interpretations of the image of Heracles that were contemporary to Antisthenes, first and foremost those presented by Xenophon, Euripides, Aristophanes, we will attempt to restore the context and the problematics of the works by Antisthenes that are dedicated to Heracles.