Leomon's 42 Deaths and Digimon's Other Heartbreaking, Soulcrushing, or Otherwise Tear-Jerking Scenes

Is this title too long? Probably? Will my answers to each season’s most tear-jerking, heart wrenching moments predictable? Maybe?

Obviously, this is a post on moments which can contain spoilers for all seasons of Digimon as well as the newer seasons like Appmon and the Digimon Adventure Tri movie series. So be warned.
And maybe also prepared with some tissues?
Digimon Adventure
Taichi and Yamato hold hands as Angemon and Angewomon throw arrows through their hearts in order to trigger the Warp Evolution of Agumon and Gabumon to defeat VenomVamdemon.
I’m not sure why, but watching this scene, even as an adult, not only gives me goosebumps but always yanks at the strings of my heart and somehow, not sure how or why, but something just gets in my eye?
Maybe it’s the nostalgia attached to this scene, maybe it’s the feeling of ‘Wow, this is BIG’, but it really stands out as not only a heart-string-pulling but also a memorable scene.
Digimon Adventure 02
So Wizarmon’s death was honestly a strong contender for the most tear-jerking scene for the first season of Digimon, however, our good Wizard friend does get a mention here somewhere – his return in 02.
The episode is pretty creepy, a ghost appears to be haunting the Fuji TV station in Odaiba, meanwhile our heroes are commemorating Odaiba Day and explaining it to our new main kids.
Later on, we see Hikari and Tailmon approaching the building with flowers, only for Tailmon to be summoned by the ghost. Everybody else is understandably freaked out, except for Tailmon who calls out to her lost friend.
This scene will always be able to give me a serious case of the leaky eyes – even when simply thinking about it.
Wizarmon then delivers a rather vague prophecy – Ken isn’t your enemy, golden radiance, there’s a true enemy, vagueness before floating off leaving a teary Hikari, Tailmon, and audience.
Yeah, Wizarmon, that’s great, why not actually tell us our good buddy Vamdemon was chilling around as a ghost in Odaiba with you? Thanks for the help buddy.
Digimon Tamers
Not Leomon’s death. It was sudden, sad, but not super tear-jerking. Maybe because Leomon’s just kind of die and it’s a meme?
However, this moment does sort of feature Leomon. Kinda.
So Juri’s trapped in a ball of despair as well as a ball of D-Reaper and there’s Juri from the Wired running around being creepy. Culumon’s also in there, because he loves her and he’s good.
Meanwhile the other Tamers are trying to get her out including, unknown to her, Beelzemon, who she had previously seen killing her precious Leomon-sama (Mr Leomon, in the dub).
At one point, some of our heroes are trying to physically break Juri out of the D-Repear’s ball. One of these characters is Beelzemon, who not actually succeeds in breaking through but does so with Leomon’s attack, causing Juri to briefly see Leomon, causing her to, understandably, break down when she sees that it’s actually Beelzemon.
Hey Juri, remember this guy? He killed your partner! Do you remember him?
Digimon Frontier
When it started
When I realised Izumi was barely a character
When the writers gave up building an interesting world
Honestly no scene in Frontier has ever made me tear up. Kouicihi’s backstory is the closest thing though, but I get more mad for him rather than sad for him. He died, his Dad is a liar, he’s a really sweet and caring character.
However this is all ruined by the fact that he died and came back because somehow five children were able to RUN INTO A HOSPITAL UNSUPERVISED INTO AN OPERATING THEATER AND CRY ON HIM AND DROP ALL THEIR PHONES ON THE GROUND THE END THEY’RE ALL HAPPY.
Digimon Savers
This is a tough one and there are two tough contenders which I uhmed and ahhed and delayed this post because I couldn’t work it out. This is the culprit.
Anyway, a scene that pulls on my eyelids and heart pretty strongly is the scene where Masaru and Agumon have to KILL Masaru’s Father who we only just discovered has actually been alive the entire time. They have to fire a laser through him to defeat Yggdrasil (temporarily). Masaru has spent the season having hope for his father being alive and carrying such admiration for his Father and letting it shape his whole personality. It’s heartbreaking but however ruined a little bit by the fact that Suguru is brought back to life at the end of the season.
Let dead characters stay dead, especially if them being alive will change absolutely nothing. I’m calling out Kouichi and Cutemon’s parents in particular here. Vamdemon can continue doing what his doing like the shiny undead child star that he is.
So, that means my heartbreaking moment is the death of Merukimon which triggers Falcomon’s next evolution.
Now I’m a pretty big fan of seeing a death and having that trigger an evolution – especially if the character manages to stay dead – so this already was destined to yank on my emotions, even more so when you think about how this was effectively Ikuto’s father figure and he’d already seen his Mother figure die in the same way (Well done to Merukimon and Yukiduramon for managing on staying dead by the way) and how Ikuto had just come to learn that maybe humans are possibly not all terrible and accept the fact that he is a human with a Digimon heart (which Merukimon’s final words are telling him to be proud of being both Digimon and Human).
It’s heart breaking and the music that plays in the original Japanese version hurts me deeply. The English dub puts in comparatively unfitting music, it’s still heartbreaking, just less so.
Digimon Xros Wars – Part One
Look, I almost had to choose Cutemon’s parents having almost deaths until I remembered how I checked the effectiveness of my tear ducts watching Baalmon die, saying how worthless he is and how he knows why he was never chosen as a warrior of light.
Xros Wars doesn’t go as deep as other seasons of Digimon but when it does it feels meaningful at least.
Digimon Xros Wars – Part Two
The death of an entire town of Lopmon.
Our heroes befriend a Lopmon from a village where, once a Choccomon becomes a Lopmon, a LadyDevimon collects it and feeds it to NeoVamdemon. Pretty dark theme, and it only continues when Shoutmon (and the befriended Lopmon) allows himself to get eaten to rescue MetalGreymon only to see possibly hundreds of Lopmon who have been eaten.
All the Lopmon (including the befriended Lopmon) sacrifice their power and, in turn, their lives, so that MetalGreymon and Shoutmon can evolve and then Double X to form Shoutmon DX by making the befriended Lopmon the legendary ‘White Lopmon’ (not Culumon) and then with its dying breath, forcing the two Digimon to touch.
It’s especially heartbreaking not only when NeoVamdemon realises he can no longer regenerate because all his power (the Lopmon) is gone, by when, at the very end of the episode, Cutemon, who has befriended the Lopmon (they’re both bunny shaped and cute), says a teary farewell to the audience. Heart. Breaking.
Well done not bringing them back to life for no reason, show.
Digimon Xros Wars – Part Three
The XrosOver.
Masaru, big bad Masaru, jumping in, out of no where, being Masaru, and punching MULTIPLE BELIAL ‘BIG BAD OF 02’ TO THE GROUND BECAUSE HE. IS. MASARU. DAIMON.
8 millions points of light? Nah, 14 year old boy.
Digimon Universe Appli Monsters
Her Mum, who is too busy working because she has to support her daugher and herself (which the season already established early on is why Eri is becoming an idol – to make her Mum smile), is watching the elections at work in the conference room and the whole office is in support of Eri. Wow family dynamics.
There are multiple amazing, heartstring-pulling, tear-jerking moments in this season but this will always take the cake.
It’s a moment that the show has effectively been building up from the moment where we first meet Eri. She goes from ranking somewhere in the middle to be ranking ALMOST in the top nine, only missing out by one place, but it’s ‘the best tenth place ever’ as told to us by a teary Astra, who has his cap covering his eyes – same, honestly.
The moment where she gets called up as tenth place is beautiful in itself, everything is silent, making the audience think “Is she still unknown?” and “Last time she ranked so high, it was an error caused by an Appmon..is it the same situation?” until we hear Dokamon call out for her…and then it’s like the sound in Eri’s mind is unmuted..everybody is cheering for her. The crowd is going wild. She earnt it.
It’s the best episode in the best season of Digimon and I need a new box of tissues.
Digimon Adventure Tri
When Tri gave up
Part Three of Tri was nonstop heart break but the clincher was at the end when Koushiro and AtlurKabuterimon, despite Koushiro spending the whole moving finding the solution, despite AtlurKabuterimon reaching Ultimate and holding all his infected friends back, they’re too late. The Digital World gets rebooted.
The music, the anguish, the sudden cut of silence as the timer reaches zero.
It’s such a hard moment?
How will Tri continue? The Digimon and their Chosen Children are seperated, the Digital World is rebooted, and the partner Digimon no longer have memories.
Well, don’t worry because Tri decides for the memory-loss thing not to be a huge issue and is more or less forgotten about until Part 6.
Alright, that’s it, 20 years, ~10 seasons, countless heartbreaks.
I’d be interested to hear other opinions for the top tearduct testing moment!
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What are your thoughts?