Samurai Vs. Samurai
Easily the most racist episode of the series, this Season 4 classic sees Jack in a restaurant ordering hot water. All seems well until the brash black man known only as "Da Sam-oo-rai" bursts into the building with a boombox blaring what sounds like early 80's hip-hop. Da Samurai is a black caricature on par with "Jump Jim Crow," an unintelligent, obnoxious, and overconfident man who is, of course, easily humiliated by our ever arrogant protagonist.
Among the strangest episodes in the series, the Season 1 finale consists of Aku, shapeshifting master of darkness, unchallenged dictator, and demigod, reading fairy tales to a group of schoolchildren. Aku is apparently trying to both soften his image and demonize Samurai Jack. Even if one ignores the obvious fact that a being as powerful as Aku has no reason to be concerned with his public perception, it is impossible to get past the fact that the impressionable toddlers somehow see through Aku's propaganda and have the courage to vocally challenge his narrative. It pays off for the children in the end, as the demonic Aku is humiliated and enforces absolutely no penalty on his detractors.
The tales of Jack's adventures have spread far and wide, and children are having fun acting out the stories. Aku, watching as the child playing him is chased around by Jack and major and minor characters from other episodes, becomes enraged and decides to spread a few stories of his own. However, it becomes apparent that he has no idea how to deal with the curious and questioning minds of youth as he calls all the children into a giant room and tells them ridiculously distorted fairy tales featuring first himself as the hero and then Jack as the villain. ...more on Wikipediasee more on Aku's Fairy Tales
Jack and the Monks
Jack climbs a mountain, aided by three silent, triplet hexagon monks. Nothing else occurs in the entire episode. A strong contender for the dubious honor of the single least entertaining episode of any cartoon ever made, this gem has all the earmarks of one of Samurai Jack's all-time duds: no influence on the main plot, a total non sequitur from the previous episode, horrible character design, and that overall sense of lazy animation that just permeates the entire episode.
After Aku's beetle drones destroy yet another gateway to the past, only moments before he's is able to reach it, Jack is overcome with frustration and is about ready to give up the quest. Then, by chance, he meets three monks about to climb the Mountain of Fatoom. Where, legend has it, truth can be found at the top. ...more on Wikipedia
Jack Learns To Jump Good
Jack meets a feral, Tarzan-esque man living in a jungle with a group of blue apes. With their help, Jack learns to jump to impossible heights. At its surface, the episode is merely annoying. But when one goes back and watches the pilot, it's hard to look past the fact that Jack was already jumping flawlessly from the series' onset. Not to mention that the episode ends with Jack apparently poised to slay Aku, right before cutting to the title card. One can only assume that Jack's timing was off and Aku sidestepped him again, flying off to a new remote outpost.
Jack tries to save a peaceful tribe that move constantly due to an opposing food-stealing tribe of monkey/lions: Jack meets up with the Monkey Boy who can ""jump good"" almost to the point of flying. Jack is taken to his village and agrees to teach a group of furry creatures to fend for themselves in return for ""jumping good"" lessons. Jack teaches the creatures to use bamboo to fight and together they set up an array of traps for the monkey/lions. In return Jack has an challenging time trying to ""jump good"", a process involving climbing hills and vines... with boulders attached to his body. ...more on Wikipedia