| No.overall | No. inseason | Title | Directed by | Storyboarded and Written by | Original release date |
| 14 | 1 | "Jack Learns to Jump Good" | Randy Myers and Genndy Tartakovsky | Bryan Andrews and Brian Larsen | March 1, 2002 (2002-03-01) |
| After his lack of jumping skills costs him a chance to return home, Jack helps a peaceful tribe of ape-like creatures and their human leader, a former child slave who escaped Aku's tyranny, defend themselves against the attacks of a larger rival tribe in return for lessons on how to "jump good", which involves gravity-defying feats. |
| 15 | 2 | "Jack Tales" | Rob Renzetti and Genndy Tartakovsky | Erik Wiese and Chris Mitchell | March 8, 2002 (2002-03-08) |
| Three short stories are presented in the following order: Jack vs. the Worm – Jack confronts a two-headed riddling worm that could grant his wish to return home. He answers a challenging riddle and allows himself to be eaten by the worm, only to learn the worm is not magical as he finds himself among disheveled old men also tricked by the worm.The Metal-Eaters – A family that feeds on metal tries to eat Jack's sword. As Jack fights them, they are exposed as robots, who eat each other.Jack, the Gargoyle and the Fairy – Jack attempts to rescue a fairy, who can only grant one wish, from a gargoyle who has trapped her in a pendant. After he awakens and defeats the gargoyle, the fairy tells him that only the gargoyle knew the magic words to free her, so Jack, who accidentally got his hand stuck in the pendant, wishes them both free. |
| 16 | 3 | "Jack and the Smackback" | Randy Myers and Genndy Tartakovsky | Chris Reccardi | March 15, 2002 (2002-03-15) |
| Jack is captured and taken to the "Dome of Doom", where he is forced to fight as a gladiator against the Dome's champions. He uses various weapons to win before reclaiming his katana and ordering the arena owner to release all the captives. |
| 17 | 4 | "Jack and the Scotsman II" | Randy Myers and Genndy Tartakovsky | Mark Andrews | March 22, 2002 (2002-03-22) |
| The Scotsman invites Jack to help rescue his kidnapped wife from robotic Celtic demons. After Jack proves himself to the Scotsman's rowdy clan, the two venture into the Castle of Boon and save the wife from being cooked into a stew. She angrily overpowers the demon army when their leader, the Master of the Hunt, calls her "fat". |
| 18 | 5 | "Jack and the Ultra-Robots" | Rob Renzetti and Genndy Tartakovsky | Bryan Andrews and Brian Larsen | March 29, 2002 (2002-03-29) |
| While investigating the destruction of several scattered villages, Jack learns that Aku's new "ultra-robot" assassins, fueled by the demon's essence, are responsible. Unable to destroy them alone, he receives unexpected assistance from Extor, the mad scientist who invented them, and calls on the spirits of his ancestors to give him the strength to slay the last robot. |
| 19 | 6 | "Jack Remembers the Past" | Rob Renzetti and Genndy Tartakovsky | Bryan Andrews and Brian Larsen | April 5, 2002 (2002-04-05) |
| After saving a village and wandering the wilderness, Jack stumbles upon the ruins of the town where he was born and recalls three of his childhood memories: meeting his first crush while chasing a cricket; witnessing a ronin in mortal combat, which sparked his interest in swordsmanship; and outsmarting bullies who stole his favorite kemari ball, which he finds in a weathered state. A robot calling for help interrupts Jack's reminiscence, and he leaves while visions of his parents look on in pride. |
| 20 | 7 | "Jack and the Monks" | Rob Renzetti and Genndy Tartakovsky | Chris Mitchell, Erik Wiese,and Charlie Bean | April 12, 2002 (2002-04-12) |
| Demoralized by the destruction of yet another time portal, Jack joins three monks seeking to climb the Mountain of Fatoom in search of "truth". After fighting a number of enemies, he declares reaching the mountaintop impossible, but the monks encourage him through visions not to give up on his quest. Reaching the top, Jack regains his conviction and once again vows to destroy Aku. |
| 21 | 8 | "Jack and the Dragon" | Robert Alvarez and Genndy Tartakovsky | Chris Reccardi and Aaron Springer | September 6, 2002 (2002-09-06) |
| Jack discovers a village overpowered by a stench emanating from a mountain-dwelling dragon with severe indigestion. At the dragon's insistence, he navigates its complicated digestive system and finds the source of the dragon's flatulence: a baby dragon spitting fire from its partially hatched egg, whom he then frees. Despite the baby dragon setting fire around the village, the villagers rejoice that they are free from the flatulence. |
| 22 | 9 | "Jack vs. the Five Hunters" | Robert Alvarez and Genndy Tartakovsky | Genndy TartakovskyMike Manley (additional storyboarder) | September 13, 2002 (2002-09-13) |
| Aku challenges the Imakandi, a group of highly-skilled leonine alien hunters, to capture Jack. They pursue him extensively through Aku City and eventually capture him, but because they value the thrill of hunting, they judge Jack to be a worthy enough target to go free before Aku can claim his prize. |
| 23 | 10 | "Jack vs. Demongo, the Soul Collector" | Randy Myers and Genndy Tartakovsky | Mark Andrews | September 20, 2002 (2002-09-20) |
| Aku sends his servant Demongo, a demon who captures and enslaves the souls of warriors to serve him, to destroy Jack. Realizing he cannot destroy the warriors' essences, Jack finds a way inside Demongo and releases numerous warriors' souls from within, allowing them to return to the physical world and overpower the demon. |
| 24 | 11 | "Jack Is Naked" | Randy Myers, Robert Alvarez,and Genndy Tartakovsky | Chris Reccardi and Aaron Springer | September 27, 2002 (2002-09-27) |
| Jack chases a mysterious rabbit, who stole his clothing while he was bathing, into a whimsical underground world, where he hides from authorities using various disguises. He ultimately learns the thief is an orphaned little girl seeking to sell his clothing, so he gives her tusks from a robot slug he fought earlier to help her make money. |
| 25 | 12 | "Jack and the Spartans" | Randy Myers and Genndy Tartakovsky | Bryan Andrews and Brian Larsen | October 4, 2002 (2002-10-04) |
| While ascending a mountain, Jack encounters a hidden society of Spartans who have fought for five generations against minotaur robots and offers to help them end the war. Together, he and Spartan king Spartok venture into a futuristic fortress to destroy a giant spider robot. Many years later, an elderly Spartok narrates how he correctly believes Jack survived the fortress's destruction. |
| 26 | 13 | "Jack's Shoes" | Randy Myers, Robert Alvarez,and Genndy Tartakovsky | Paul Rudish and Charlie Bean | October 11, 2002 (2002-10-11) |
| When robot bikers destroy his sandals, Jack seeks revenge but realizes that he cannot do so without footwear. After unsuccessfully trying out a variety of shoes, he follows a boy with sandals like his to a traditional Japanese family home secluded in a jet engine repair shop, where the boy's father makes him new sandals. |