Digimon Adventure/Tear Jerker

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• Episode 13, when Angemon sacrifices himself to protect TK and the other chosen children.
• Episode 22, where Matt tells TK he's leaving for a few hours and never returns. TK was in 2nd grade. This could border on nightmare fuel.
• Episode 23, paired with a crowning moment of awesome. Joe is working at restaurant to repay a debt. Matt stumbles upon the restaurant to help, but is easily convinced by Demi Devimon that Joe is messing up on purpose. Joe puts himself in lethal danger to save TK. This episode is supposed to be Matt's, but it should have been Joe's. Joe saves TK more often than the others.
• Episode 26, Biyomon wants to protect her friends from their newest enemy, Myotismon, but Sora holds her back and tells her not to or she'll get hurt. Biyomon cries "Sora, why can't you understand me?" Cue Sora realizing that she's behaving like her own mother towards Biyomon, so that this whole time, her mother was always overprotective because she loved her and was looking after her. Biyomon/Birdramon then attacks Myotismon only to be impaled in the chest by Myotismon's attack. Sora cries "Birdramon, no! I love you!" And then her crest of love glows. Made poignant by the fact that Sora's been feeling this whole time like she's never known love and can't truly love anyone. This is also very much a Crowning Moment of Heartwarming.
• In The Movie, the part taken from the Digimon: Adventure short film, when Greymon battles Parrotmon. Who doesn't want to cry when two kids are seeing their first Digimon have to duke it out and almost die? Of course, this soon turns into a Crowning Moment of Awesome when Tai wakes Greymon up the same way Kari awoke him (with her whistle), and he kicks that goddamn bird's ass.
  • Her dialogue just as sad in the dub...As Tai wakes up in the middle of the rubble, Kari is already awake, shouting for Greymon: "Greymooooon! Come back! Don't you wanna play horsie?!"
• The end of episode 21: Kari wordlessly begging her brother not to leave her and his sorrow as he realizes he has to leave her again are nothing short of heartbreaking...the music doesn't help.
• Gatomon's back story is one giant Tear Jerker. She is accidentally abandoned, waiting all her life for her "special person" only for her to never show up, and then picked up by Myotismon only to be abused and warped into a super-soldier? It's too much.
• Wizarmon:
  • Diving Save.
  • Not only that, but his reappearance as a ghost years later rubbing salt in the old scars this troper got an entire season ago at elementary school age - when her recent searching for old Digimon episodes dug it up, not only did it sting all over again, she thinks she may have uncovered the subconscious reason she takes of all things the song Who Knew by Pink dead seriously. Gatomon tries to take his hand, she's in tears the whole time, just... GAHHHH.
  • That has got to be the saddest moment in all of the first season... because he doesn't get better. Since he died on Earth, he was unable to trun into a Digi-Egg.
    • Tell me where it says that?
• Oh, most definitely... Especially when he and Gatomon try to hold hands. Her hand passes right through his...he looks sad, and whispers "I'm sorry," before vanishing, leaving her and Kari in tears. The new Digidestined ask who that was, because they, of course, have no clue.

Gatomon: ...a friend.

• Izzy's backstory. That's all. Even Tentomon was bawling when he learnt about it.
• The mass memorial that followed Whamon's death--Wizardmon, Chuumon, Piximon, and now Whamon--was what did it for me. The fact that this was that early in the Dark Masters arc says so much.
• Leomon's death and Ogremon's reaction to it
  • Fridge Horror when you realize of all the dead digimon by this point that come back,Leomon isn't one of them thus starting the tradition of killing Leomon forever
• Tai's story about how his little sister Kari nearly died because of his irresponsible actions when he was just a kid. What really hurt were Kari's first words back from the hospital: ("Tai.. I'm sorry I can't kick the ball very good. You'll probably never want to play with me again").
• For some, Puppetmon's death.

Puppetmon: Cherrymon....what do those kids have that I don't? Cherrymon: Friends...

• Don't forget all the Numemon teaming up against Machinedramon, only for all hundred or so to be killed with one punch. As a matter of fact, pretty much anything the Dark Masters do leads to this. Things like Whamon being skewered and Puppetmon's Bad Boss habits won't leave your mind easily.
• Episode 51 had both Matt and Sora trapped in caves formed by the darkness in their own hearts. Matt, in particular, was angsting over feeling alone, thinking Tai was a better brother than he was. But Gabumon was able to pull him out of it by reminding him he wasn't alone...
• The last episode of Digimon Adventure and three preceding it. this makes it even sadder.
  • To elaborate: Palmon doesn't want to say goodbye, as she knows it's going to be too difficult; she even hides from Mimi as the latter runs through the forest searching for her. Some Geckomon, however, bring the poor thing out of depression by raising the point that not going to see Mimi off will be worse. So, later, as Mimi's crying on the flying tram car, Sora looks out of the window and suddenly shouts to Mimi to look out the window. And cut to the lone Palmon running, crying and shouting to Mimi. She's then joined by the other partner Digimon in a rousing chorus of Butterfly, acapella.