The Infernal Regions seem like a perpetually fascinating topic. Which of the many, many versions of Hell/Hades is your favorite? For me it’s currently a tossup between the now-defunct webcomic Jack and the newer animated series Helluva Boss.
Night Gallery episode w/John Astin. Man goes to hell, and it’s BORING, BORING, BORING.
Larry Niven’s Inferno, inspired by Dante.
Of the Far Side cartoon, where everyone is given an accordion.
No, I’m sure I prefer Niven.
Does Robot Hell from Futurama count as a depiction of Hell?
Hard to beat Dante’s.
Though, come to think of it, there is that scene in the Book of the Dead where Anubis weighs the guy’s heart, and if it is heavier than a feather, he gets devoured by a monster. That is hard-core.
Off the top of my head, C. S. Lewis’s in The Great Divorce.
From the second volume of the Chronicles of Master Li and Number Tex Ox, Story of the Stone, by Barry Hughart, we are given a vision of the (a?) mythological Chinese hell, in which sinners are punished for their transgressions in preparation for their reincarnation.
Master Li and Number Ten Ox, still very much alive, invade hell pretending to be flunkies for the emperor who have found a soul whose memory wasn’t properly cleansed before reincarnation, indicating an abysmal bureaucratic failure among the demons and other underworldly apparatchiks whose job it is to tend to the existence between lifetimes with superior administrative acumen.
It’s a caper story into the land beyond life – and just a small slice of the novel as a whole – and no other hell I’ve ever seen has come remotely close.
In The Culture series of books by Ian M. Banks the digitalization and uploading of your consciousness is a well know and widely used technology, usually for benevolent purposes. Except in one of the books it is revealed that some more conservative civilizations have literally invented hell and upload the consciousness of people they deem undesirable into it. It is… brutal.
Elaine, “I’m going to Hell! The worst place in the world! Those Devils and those caves and the ragged clothing. And the heat, my God, the heat!”
Wayne Barlowe (famous for Barlowe’s Guide to Extraterrestrials) had an interesting concept in Barlowe’s Inferno:
Demons use damned souls for construction material. If a demon wants to build a house, he grabs a soul, shapes it into a brick, and uses it to build his house. If he wants to build a machine, he grabs a soul, shapes it into a part, and uses it to build his machine.
It’s all completely random, and completely impersonal. You are not receiving any particular punishment for any particular sin. You simply don’t matter any more.
Barlowe is an artist. To him, hell is being paint on someone else’s canvas.
Night Gallery episode w/Arte Johnson as ultra-hip DJ who has to listen to Muzak for all eternity.
I don’t know if I have seen that one, but there is the classic Twilight Zone episode with the gangster who dies and thinks he’s gone to heaven – surrounded by hot women, always wins at the casino, etc. until it becomes so boring and monotonous that he decides he’d rather be in “the other place”, only to discover he’s already there. (IIRC Sebastian Cabot played his guardian “angel”.)
Would that be as opposed to a truthful and accurate depiction of hell?
Night Gallery episode w/John Astin and Phyllis Diller. He kills his endlessly talking shrew of a wife then has to spend eternity listening to her yak.
Or the Twilight Zone episode where a criminal is gunned down by the police:
He finds himself in a nice hotel room where his own personal guardian angel named Pip (played by Sebastian Cabot) tells him all he has to do is ring and Pip will grant him any wish. He can’t believe his luck getting into Heaven and figures a mistake was made.
Women all love him and when he gambles he can’t lose. Everything invariably goes his way. He becomes very bored with no challenges. He says to Pip, maybe I belong in the other place. Pip: But you ARE in the other place mwhahahahahaha! Pip isn’t an an angel at all, but a demon!
Sounds familiar… 
In American Hell, you have to eat a shovel of shit each day.
In Soviet Hell, you have to eat two shovels of shit a day. But half the time there’s no shit, and in the other half, there aren’t any shovels.
James Branch Cabell’s ‘Jurgen’ has a delightful visit to hell:
"Afterward Jurgen abode in Hell, and complied with the customs of that country. And the tale tells that a week or it might be ten days after his meeting with Florimel, Jurgen married her, without being at all hindered by his having three other wives. For the devils, he found, esteemed polygamy, and ranked it above mere skill at torturing the damned, through a literal interpretation of the saying that it is better to marry than to burn.
…
Thereafter Jurgen abode in Hell, and complied with the customs of that country, and was tolerably content for a while. Now Jurgen shared with Florimel that quiet cleft which she had fitted out in imitation of her girlhood home: and they lived in the suburbs of Barathum, very respectably, by the shore of the sea. There was, of course, no water in Hell; indeed the importation of water was forbidden, under severe penalties, in view of its possible use for baptismal purposes: this sea was composed of the blood that had been shed by piety in furthering the kingdom of the Prince of Peace, and was reputed to be the largest ocean in existence. And it explained the nonsensical saying which Jurgen had so often heard, as to Hell’s being paved with good intentions.
“For Epigenes of Rhodes is right, after all,” said Jurgen, “in suggesting a misprint: and the word should be ‘laved.’ ”
This was my immediate thought as well.