Story 1: Jack vs. the Worm
Jack enters the land of the magic worm and confronts it to ask it to grant him a magic wish.
Upon summoning the worm from its lake, the worm is revealed to have two heads. The worm proposes a challenge to Jack. One head tells only truths while the other tells only lies. Using only one question, Jack must choose which head is the true magic worm and then allow that head to eat him. If he guesses right, he will be transported to magical land where his innermost desire will be fulfilled. If he guesses wrong, he will be slowly digested over 500 years. After thinking it over, Jack asks "If you were your brother, which one would you say is the magic worm?" The right head answers that it would be the left one. Jack concludes that the right head is the magic worm since if he were the truthful worm, he would truthfully say what his lying brother would say, and if he were the lying worm he would lie the opposite of what his brother said. The right head proceeds to swallow Jack, while the left head reveals that both heads are liars and they aren't magic at all. Jack realizes this as he finds himself in the worms stomach surrounded by several old men who were also tricked by the worm.
Story 2: The Metal-Eaters
At night, Jack confronts a 'family' of cannibal robots who hunger for his magic sword.
They approach him at night, pretending to be an ordinary family whose village has been attacked. Jack says he is sorry he was not aware of this so that he could have helped and asks them to have dinner with him by the fire. As they sit by the fire, they watch hungrily as Jack sharpens his sword. They suddenly attack him and make several attempts to eat his sword, Jack fights back and slashes the mother's face with his blade, resulting in the skin of her face being torn off, exposing the metallic skeleton under it. After the family members realize that they're all made out of metal, they begin to attack and eat each other, leading to their own demise.
Story 3: Jack, the Gargoyle, and the Fairy
Once Jack climbs the tower, he finds out that the fairy is inside a magic ball and the gargoyle is sleeping, thus he tries to take the fairy out by his hand, only to have it get stuck in the ball as well. Jack decides to steal the key, which is worn by the gargoyle as a necklace, and succeeds. Unfortunately, he wakes the gargoyle up after in a vain attempt to unlock the ball with the key and making too much noise by doing so. The gargoyle assaults Jack and gets killed by him after a short fight. Then, the fairy tells Jack that the only way the key could have worked is with secret magic words that only the now-dead gargoyle knew. She then expresses her sadness, saying that they will never be free. After spending some time thinking, Jack finally smiles and wishes that they were both free.
- Casting by
- Collette Sunderman
- One of the worms is voiced by renowned English actor Tim Curry.
- Jeff Bennett, who voices the Gargoyle, also voiced another gargoyle character named Brooklyn in the Disney TV series Gargoyles.