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Tear Jerker: Samurai Jack
Near the end of episode L (#50), when X9, now powering down, and dying, asks Jack to take care of Lulu. Cue Jack showing a worried expression at possibly killing a perfectly innocent robot.
Made all the more worse knowing that you, as a viewer, could predict the ending before it transpired. It was only a matter of time before Jack got the drop on X9 and slew him. What makes it worse? That it's a Deconstruction story told from the perspective of a random robotic mook who had a life and an existence up until he was took out by Jack for whom it was Tuesday. Imagine how many other bots before him lived.
"Lulu... sweet thing."
Jack's sword doesn't hurt the innocent. Either it saw X9 as guilty, or... it does not recognize machines.
Jack and Lava Monster features Jack fighting his way through a maze of death only to confront a near-invincible giant lava monster. Then we learn that the lava monster was actually a Viking warrior, imprisoned by Aku in solid stone. He learned to form the stone around him into a monstrous body, and can only be freed to enter Valhalla if defeated by another warrior in honorable combat. Which Jack does, sending the fallen Viking on to eternal rest.
I think you're referring to "Jack and the Monks.":
"Have you FORGOTTEN!!??"
Even the early parts of that episode are heart-wrenching. At a few points Jack just sounds so defeated.
"Jack Remembers the Past" is heartbreaking.
The worst part is when he sees his familly crest on the bell, and he realizes where he is and starts crying.
Jack:(falls to his knees): my home...
"Jack and the Warrior Woman." Sure, most viewers were certain that Ikra was evil and was going to betray Jack, but that almost made it worse! The audience guessed it, Jack could have guessed it, he really should have known, but he was too sad, lonely, and kind to. Let that be repeated, in this story, a multi-episode Story Arc ends in the gut-wrenching defeat of the hero, because said hero was too sad, lonely and kind! And this was just the 6th episode!
YMMV, but the fact that such an amazingly different and daring show, the likes of which have, for the most part never been seen before, ended without a big bang or an epic duel or something similar, and the supposed ending is stuck in limbo, is one big tearjerker for fans of the show.
Even more so when it was announced in late 2013 that the show was returning to adult swim Toonami. To long time fans of the show who do not get Boomerang this was seen as great news...until the announcement came that because they were under contract to keep original Naruto, the show will be seen..at 4AM! Not only that, but when Attack on Titan premiered the show was pushed BACK..to 4:30! Talk about not getting any love!
And starting in June it will be removed from Boomerang ENTIRELY! Which means adult swim Toonami will be the ONLY place to see it! LET;'S GIVE THIS SHOW SOME LOVE, PEOPLE!! LET'S GIVE IT LOVE!
Apparently not too many people were, cause starting July 27th, the show will be moved again...to 5:30 AM, thus being the one to close out the block! WHY does Jason Demarco hate this show so much?!?!
Although, a movie is in production. This could be the ending the fans waited years for. Aku's voice actor (Mako Iwamatsu) died in 2006, but we'll cross that bridge when we get there.
The ending of "Princess and the Bounty Hunters" was particularly heart-wrenching. Princess Mira, an Anti-Villain who's only some motivation to claim the bounty on Jack was so that she can free the oppressed people of her country, works hard the entire episode to set up a well-laid trap. In the end, Jack Curb Stomps the bounty hunters, only leaving her alive. When she realizes she can't defeat Jack, she drops her weapon and cries, solemnly accepting that she can never save her people. It's sad to see her so tragically accept this fate, even though Aku would probably not free her country anyway. What makes it worse is that Jack doesn't even acknowledge her presence or offer to help her, even though they could have easily been great allies or even friends. What makes this even more tear jerking is that, knowing Jack like we do, he would have gladly helped her without hesitation. All she had to do was ASK. But she's too filled with pride to do so.