The Ferryman

This scary looking old man is Charon.                                                              He is frequently in the art of ancient Greece. Attic funerary vases of the 5th and 4th centuries B.C. are often decorated with scenes of the dead boarding Charon’s boat.

On the earlier such vases, he looks like a rough, unkempt Athenian seaman dressed in reddish-brown, holding his ferryman's pole in his right hand and using his left hand to receive the deceased.

Hermes sometimes stands by in his role as psychopomp. On later vases, Charon is given a more “kindly and refined” demeanor. Aristophanes, in The Frogs, had him spewing insults regarding people's girth.

In the 1st century B.C., the Roman poet Virgil describes Charon in the course of Aeneas’s descent to the underworld (Aeneid, Book 6), after the Cumaean Sibyl has directed the hero to the golden bough that will allow him to return to the world of the living:

There Chairon stands, who rules the dreary coast -

A sordid god: down from his hairy chin

A length of beard descends, uncombed, unclean;

His eyes, like hollow furnaces on fire;

A girdle, foul with grease, binds his obscene attire.

Other Latin authors also describe Charon, among them Seneca in his tragedy Hercules Furens, where Charon is described in verses 762-777 as an old man clad in foul garb, with haggard cheeks and an unkempt beard, a fierce ferryman who guides his craft with a long pole.

When the boatman tells Hercules to halt, the Greek hero uses his strength to gain passage, overpowering Charon with the boatman's own pole.
In the second century, Lucian employed Charon as a figure in his Dialogues of the Dead, most notably in Parts 4 and 10 (“Hermes and Charon” and “Charon and Hermes”).

In the thirteenth century, Dante Alighieri described Charon in his Divine Comedy, drawing from Virgil's depiction in Aeneid 6. Charon is the first named mythological character Dante meets in the underworld, in the third canto of Inferno.

Elsewhere, Charon appears as a cranky, skinny old man or as a winged demon wielding a double hammer, although Michaelangelo's interpretation, influenced by Dante's depiction in Inferno, canto 3, shows him with an oar over his shoulder, ready to beat those who delay (“batte col remo qualunque s'adagia”, Inferno 3, verse 111). In modern times, he is commonly depicted as a living skeleton in a cowl, much like the Grim Reaper or Dickens' Ghost of Christmas Yet to Come.

In [[Percy Jackson and the Lightning Thief]], Charon is first depicted as "tall and elegant, with chocolate coloured skin and bleached blond hair shaved military style". although as he enters the underworld he morphs into a skeleton.
h/t wikipedia

Here Charon is seen using his paddle to persuade souls and sinners to board his boat to be ferried across Hades.

Both these drawings were by Gustave Dore