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Top 10 Saddest Digimon Moments

VO: Dan Paradis
Written by Alex Crilly Mckean Prepare to cry digital tears. Welcome to and today we are counting down our picks for the top ten saddest Digimon moments. For this list, we’ll be looking at the most depressing and bittersweet moments from across this anime franchise. As such, be on the lookout for a whole ton of spoilers down the line. Special thanks to our users Shawn Mark, blademon4, and SjamSjam3 for submitting the idea on our interactive suggestion tool: WatchMojo.comsuggest

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Top 10 Saddest Digimon Moments

Prepare to cry digital tears. Welcome to and today we are counting down our picks for the top ten saddest Digimon moments.

For this list, we’ll be looking at the most depressing and bittersweet moments from across this anime franchise. As such, be on the lookout for a whole ton of spoilers down the line.

#10: Rebooted

As you might have expected, a series of films celebrating the original anime was going to contain a tremendous amount of emotional baggage. The third instalment of Digimon Adventure tri, known as Confession, takes this to a whole other level as our favourite Digi-pals become infected with a mysterious virus, all the while the Digital World is on the verge of rebooting itself. If that wasn’t bad enough we have to watch Tentomon fend off his afflicted-friends before the imminent reset.

#9: One Lonely Puppetmon

Sure the guy may have been mentally unstable and liked to kill anyone who disagreed with him, but there was just something about this particular Dark Master that we felt kind of sorry for. He actively went out of his way to try and play around with TK … even if it was in a really creepy kind of way. In his final moments before death he wondered why he couldn’t defeat the Digidestined, only to recall upon the words of an old ally (which he had previous murdered) that it was because he lacked any real friends.

#8: Kari’s Incident

Tai for all intents in purposes is a very protective older brother, especially since his little sister hasn’t always been in the best of health growing up. After being separated from her, Tai reveals that when they were much younger he took a sick Kari outside to play, which nearly ended up killing her as a result. We’re not sure what’s more upsetting here; Tai’s regret or the fact Kari nearly kicked the bucket. it’s a very dark, yet realistic scene that you wouldn’t have thought would find its way into a series about with talking monsters.

#7: The Death of Piximon and Chuumon

The Dark Masters certainly had a lot to live up to when they were introduced as the final group of villains for the Digidestined to face. What did they do to prove their infamy? They slaughtered every side character they came across. This unfortunately included the Digidestined’s one time adorable mentor figure Piximon as well as the comic relief sidekick known as Chuumon. While we may have scoffed at them in the past, seeing them erased from existence was heartbreaking.

#6: BlackWarGreymon’s Sacrifice

He may have knocked the crap out of them on numerous occasions, but over time due to his longing to understand the true nature of the heart, BlackWarGreymon turned into something of an anti-hero who wanted to forge his own path. This all came to a head when he decided to give his life in order to seal off the Digital World, protecting it from Oikawa and his cronies. He lived a warrior, and chose to die a hero.

#5: The Death(s) of Leomon

Not to make light of a character’s untimely demise, but man does this guy have the worst luck, since he repeatedly meets his maker multiple times throughout the franchise. In Digimon Adventure, he faded out of existence while making his peace with his rival while in the third Digimon Adventure tri movie he also finds himself getting deleted. But undoubtedly the most heart-wrenching moment came from Digimon Tamers, where he is mercilessly torn apart by Beelzemon while trying to protect Jeri.

#4: Ken Has a Change of Heart

It’s no secret that at the start of Digimon Adventure 02, Ken was something of a jerk. He turned Digimon into slaves all the while declaring himself emperor. There was also the fact that he was verbally and physically abusive to his supposed partner Wormmon. However, Ken’s reckoning finally came after Wormmon died in his arms. This moment would serve as the tipping point for Ken to abandon his evil ways and truly appreciate his partner.

#3: The Death of Wizardmon

Digimon has no shortage of heroic sacrifices. But without a doubt this was the one that had all fans in tears. Taking the brunt of the fiendish Myotismon’s attack, the benevolent Wizardmon dies in the arms of Kari and Gatomon as he reflects on how, despite the course his life took, he was happy have a friend like her at the end of it all. While this leads into another action scene, most of us are still too traumatised to process what just happened.

#2: So Close Yet So Far

Yukio Oikawa, above all else, was a weak man who was manipulated due to his childhood desire to one day see the Digital World for himself. After serving as MaloMyotismon’s unwilling pawn, his body begins to waste away. Despite his mini-redemption arc as well as being so close to seeing the Digital World for himself, he doesn’t quite get to cross that final threshold. After being put through so much, even getting his own Digimon on the fringe of death, seeing Oikawa miss out on a happy ending is soul destroying.

Before we reveal our number one pick, here are a few honourable mentions.

The Death of Pumpkinmon and Gatsumon

Thomas’ Mother

The Death of Mama Frigimon

#1: Goodbye

Practically every entry in the franchise has it, and every time it becomes harder and harder to watch. After defeating the great evil that threatens both the human and Digital Worlds, the Digidestined have to say goodbye to their beloved partners, which always results in plenty of tears and cries of affection. Digimon Frontier gave us a more upbeat and comedic twist, Digimon Tamers was just downright depressing with theirs, but of course the one everyone remembers the most is at the conclusion of the original series where the Digimon let loose their final heartfelt farewells.

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