Charon

“Abandon all hope, ye who enter here.” — Charon

Charon is the ferryman of the dead who appears as an anthropomorphic boat with a giant ship for a body. His sworn duty is to ferry the souls of the damned across the infernal River Acheron, to Limbo beyond. Although he is physically incapable of directly attacking people due to his lack of any actual limbs save for the head, Charon is able to summon various demons to fight Dante. He is later killed after Dante uses an Asterian Beast to tear his head off. His severed head is later shown within the Citadel of Limbo, still repeating the inscription from the Gates of Hell. Once approached, the player is prompted with a quick time event to push him back into the abyss. Doing so will unlock the Burning Eyes achievment/trophy. His head is later shown in the river Styx serving as a nest for Pests.

Loot

Charon's Oar - After falling to the damned climb, keep moving left and jump the gap to find the relic.
Silver Judas Coin - Push the crate all the way to the left side of the room and you'll be able to reach a hidden ledge with a fountain contianing the coin. (Silver Piece 4).
Orpheus - Jump on the crate and then onto the high platform at the end of the room (above the jail cells).

Trivia

In Greek mythology, Charon was the ferryman of the Underworld, who's duty was the ferry the souls of the dead across the Rivers Acheron and Styx.
According to Hesiod's Theogony, Charon is considered to be a child of Erebus (Primordial God of Darkness) and Nyx (Primordial Goddes of Night. He is also related to other figures in Greek Mythology, including Thanatos and Hypnos.
In Greek burial custom, the dead were buried with a single coin, a drachma, placed upon their tongue. Archaeologists believe this was placed so as to pay the ferryman for passage across the river (This could be why the developers placed a Judas coin aboard Charon).
In "The Inferno", Dante also placed Charon as the ferryman of Acheron. His job was to ferry the souls of the damned across Acheron, and into Limbo.
Charon's Ferry appears as an arena in the Trials of St. Lucia DLC.
Charon's voice is acted by Bart McCarthy, the same actor who voiced Virgil.