Charon was the ferryman who brought the undead across the River Styx and the River Acheron into the Underworld. He was the son of Nyx and Erebus, Night and Darkness, so it appears he was somewhat predestined by dint of birth to undertake his sombre and dreary job. I think he worked for minimum wage too since all he collected were the obols (coins) placed in the mouth of the dead by way of their fare into the Underworld.
My first challenge in drawing Charon was factoring in drawing the boat. I think I have seen classical images of the boat depicting it as being a rather shallow skiff. My attempts to sketch a gondola type boat, however, ended up looking like skinny bananas. Had I more time, I am sure I could have gotten it looking right enough but I didn’t so I had to problem solve and my solution was to place the boat face on so I only had to draw the prow. Much easier. This also meant I could draw Charon front on rather than in profile. I decided to make Charon cadaverous in order to strengthen the association between him and his role as courier of the dead so I made him angular and stooped and gave him a skull mask to conceal most of his human face. His look was completed with the Grim Reaper cloak.
Doesn’t he look miserable?