Charon

Here is my version of Charon (or Haros), the ferryman of the Underworld from Greek mythology ! Like Thanatos, Hypnos and the Moirae, he was fathered by Nyx, the primordial goddess of night, and Erebus, the primordial god of darkness. He is described as a neglected and surly old man, with a long beard and burning eyes according to Virgil.

His role was to lead the souls of the deceased to their new abode, crossing the Styx, the main river of the Underworld, but probably also its branches, such as the Acheron (which would make the link between the world of the living and the Styx itself), the Cocytus, and the flaming Phlegeton (although another ferryman called Phlegyas sometimes takes Charon's place on this particular river). But it would appear that Charon is not active on the Lethe, the river of oblivion that the blessed dead crossed before coming back to life in another form.
However, to be able to cross these underground waters, it was necessary to pay the sinister boatman. Those who had not been decently buried, or who had not received an obol from their relatives, deposited on or inside their mouths, were condemned to wander on the infernal shores for 100 years.

Only six living people were able to cross the Styx without following these rules. Aeneas did this by giving Charon a golden branch entrusted to him by Apollo, for that was the price of the crossing for the living. Heracles, true to himself, used force against Charon, having seized the latter's pole, and did so both on the way out and back, which earned Charon a year of imprisonment ( to the question "who took his place during this year?", we have no answer...). Heracles had come here to free Theseus and his friend Pirithous, who themselves had entered the Underworld while being alive to kidnap Persephone. But Heracles only managed to free Theseus, since Pirithous had been trapped by a cave-in provoked by Hades. As for Orpheus, who had gone to look after the late Eurydice, he charmed all of the Underworld with his music, and the ferryman was no exception. And finally, the beautiful Psyche was able to go there and back by simply paying Charon with oboli, instead of the golden branch asked of the living.

Charon, however, is not to be confused with the Etruscan god Charun who, although being also a psychopomp entity escorting the dead in the Underworld, is never represented on a boat, is given a hammer, and multiple more monstrous features : wings, tusks, large pointed ears, as well as snakes wrapped around his arms ...