Hippias Minor, or On Lying, is thought to be one of Plato's early works. Socrates matches wits with an arrogant polymath, who is also a smug literary critic. Hippias believes that Homer can be taken at face value, and he also thinks that Achilles may be believed when he says he hates liars, whereas Odysseus' resourceful behavior stems from his ability to lie well (365b). Socrates argues that Achilles is a cunning liar who throws people off the scent of his own deceptions and that cunning liars are actually the "best" liars. Consequently, Odysseus was equally false and true and so was Achilles (369b). Socrates proposes, possibly for the sheer dialectical fun of it, that it is better to do evil voluntarily than involuntarily. His case rests largely on the analogy with athletic skills, such as running and wrestling. He says that a runner or wrestler who deliberately sandbags is better than the one who plods along because he can do no better.

In Hippias Minor, Socrates argues with Hippias about which kind of liar is the best, the man who deliberately contrives a lie, or the man who lies unwittingly, from not paying attention to what he is saying, or changing his mind. Socrates argues that the voluntary lie is better than the involuntary lie.

The debate is rooted in a literary question about whom Homer intended to portray as the better man, Achilles or Odysseus. Socrates says he has heard Eudicus' father, Apemantus, declare that there is a parallel analogy between the artistic quality of the Iliad and the moral quality of its main character, Achilles, and the quality of the Odyssey and the quality of its main character, Odysseus. The men do not pursue this thesis, that the moral status of the characters in a work of literature has some bearing on its artistry. Socrates does resurrect the idea in the Republic, however, when he argues that Homer's classics would be better books if Achilles and the other warriors were presented as always righteous. Socrates says that they ought to be rewritten to this effect.

Hippias objects, saying that the laws punish people who harm others deliberately with purposeful lies, and are more apt to excuse those who do harm by making mistakes. Socrates insists that those who injure people, tell deliberate lies, and err voluntarily are better than people who simply make mistakes (372d). Hippias suspects at this point that Socrates is being dishonest in the debate. Socrates counters that if he is troublesome, it is unintentional, that if he were being difficult deliberately, then he would be wily, which he is not. This is a kind of liar's paradox.