Dürer's journey to Italy in 1494 gave him the opportunity for the first time to study classical subject matter, particularly the depiction of the nude and of antique drapery. He returned to Nuremberg in 1495 with a great interest both in Italian art and in antiquity, an enthusiasm which his close friends, the leading humanist Willibald Pirckheimer and the poet Konrad Celtis encouraged by introducing him to literary sources both ancient and modern.
The parable alluded to in this engraving is first recorded by Xenophon and describes the young Hercules encountering Vice and Virtue. Vice, personified as a seductive, unclothed woman reclining in the lap of a satyr, attempts to lure Hercules into a life of luxury and pleasure. Her clothed counterpart, Virtue, proposes an alternative way of life, one shaped by courage and hardship. Hercules decides on the virtuous path and goes on to kill the Nemean lion. Durer's depiction of this encounter, however, differs in several important respects to Xenophon's account, which has led to much speculation as to whether or not this is the actual source. In Dürer's composition Virtue is seen assailing Vice with a branch, yet there is some ambiguity in the role played by Hercules, as co-assailant or defender of the fallen Vice.
Whatever the interpretation, the print has been much appreciated, both for the characteristically beautiful rendition of a northern landscape as well as for Dürer's developing depiction of the male and female nude (which would reach its apotheosis in Adam and Eve (of 1504) and in particular for Hercules' taut musculature, which must have been inspired by Antonio Pollaiuolo's famous engraving of the Battle of the Nudes (circa 1470-75).