Ray Henwood (King Sisyphus) and Leslie Wing (Queen Karis) had played the same characters in the Xena: Warrior Princess episode "Death In Chains", broadcast the week previously to this episode. However, much of the details between the two stories are different. The fate of Sisyphus in this episode helps lead into the following year's XWP episode, "Ten Little Warlords", though only Sisyphus appears in that and is played by a different actor.
Leader: Hercules, you're coming with me.
Hercules: (turning his back on him) I don't think so. For openers, you didn't ask politely.
Leader: You can come the easy way, or the hard way. It's up to you.
Hercules: Am I losing my hearing? Because I still didn't hear please.
Hades: (warning Hercules to hurry catching Sisyphus) Oh, and you only have three days.
Hercules: Why only three?
Hades: Two reasons. First off, if the final resting place for his spirit isn't designated within three days it's doomed to wander forever.
Hercules: It's a good reason. What's the second?
Hades: I got inventory coming up.
Iolaus: (trying to bluff his way past Sisyphus' guards) Hi, I'm Uranius, and this is my friend Plutonius. We're in the mineral rights business.
Guard: (asking Hercules) That true? This... 'mineral rights' stuff?
Hercules: I'm more into human rights myself.
Hercules: (after running into a second set of guards) I thought you said this was a secret entrance!
Soldier: (waiting in line for Charon's boat) Hurry up and wait, hurry up and wait. You'd think the army would be different when you're dead.
The title of this episode is a play on words of the AC/DC song, "Highway to Hell".
When Charon spies Hercules he tells his workers to hide the lanterns, it's a reference to Hercules stealing his lantern in "Hercules in the Underworld".
When Hades shows Timuron's fate should Hercules not rescue him, rolling a boulder up a hill in Tartarus for all eternity, Hades is showing the punishment that Greek mythology actually assigned to Sisyphus. However, according to the myth before Sisyphus died he had told his wife that when he was dead she was not to offer the usual sacrifice. Once in the Underworld he complained that his wife was neglecting him and persuaded Persephone to allow him to go back to the upper world and ask his wife to perform her duty. When Sisyphus got back to Corinth he refused to return, and was eventually carried back to the underworld by Hermes.
Sisyphus also tells Hercules in this episode that he is being called to the Other Side early as punishment for revealing one of Zeus' love affairs with one of Sisyphus' nobleman's daughters. In the myth it isn't a human girl, but Aegina, the daughter of the River God Asopus that Zeus was trying to seduce, and her father that Sisyphus told.
Epicurus was an ancient Greek philosopher who taught that pleasure was the highest good that man could attain. His teachings were distorted by those who didn't understand them into a lifestyle centered around finding new ways to sate the appetite, while what he actually taught was that a man who was ruled by his appetites could never satisfy them, and therefore never truly be happy.
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