Cassandra has a dreadful vision of kissing the school freak Icarus and makes a deal with Hades to prevent it, but when Hercules attempts to break the contract, with the aid of Aphrodite, he sets in motion a series of hilarious misunderstandings.

Hercules finds himself hired by a bunch of nerdy "abacus geeks" when they enlist him to protect them from rampaging centaurs that pillage the town weekly.

Icarus' bright idea once again backfires when he talks Hercules into visiting the Fates to convince them into reweaving their cosmic Tapestry so that the boys can score some hot concert tickets. However when they refuse, Icarus takes things into his own hands and messes with the Tapestry himself and trouble insues.

Ares sends his two sons, Fear and Terror, to kidnap Athena's precious Owl of Wisdom when she angers him. But the joke's on him when Athena entrusts the magical bird to Hercules for protection.

Queen Hippolyte kidnaps her daughter, Tempest, and makes her undergo a savage initiation ceremony to regain her status as a warrior and to earn the right to wear the Golden Girdle. Meanwhile, Hercules attempts to follow in a misunderstood rescue attempt.

Phil needs a housesitter, so that he can go to a convention and Hercules volunteers to watch his island for him, however things go from bad to worse, when Hercules throws a party and is busted by Poseidon.

Hercules wants his chariot license to save face in front of Adonis. Meanwhile, Hades bets Zeus the deed to the Elysian Fields that Hercules won't get his license by sunset, and Pain and Panic are on hand to help.

Icarus poses as a cupid so he can get a love arrow to make Cassandra love him, but the joke's on him when he accidentally uses "loathe" arrows instead. Meanwhile, Pain and Panic get a hold of the loathe arrows and create havoc all over the country.

When the Academy decides to put on a play for the gods, Hades hires Pain and Panic to carve a magical rock that will make all the gods go to sleep and uses Icarus as bait.