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  • Accidental Innuendo: Tai is especially guilty of this, particularly because of his tendency to say he needs to "hook up" with the others rather than use the much less sexual sounding "meet up". Examples of this include episode 22, in which he said he needed to "hook up" with the others, and episode 36, in which he told Sora to "hook up" with Matt.
  • Complete Monster: This series has three: Myotismon, Piedmon, and Machinedramon.
    • Myotismon was the most sadistic and psychopathic villain in the initial anime series. A Nightmare Soldier Digimon with aspirations to fuse the Digital World with the real world into a singular underworld for him to rule over, he took in Gatomon under his wing only to abuse and assault her to the point she became his loyal killing machine. He also routinely tortured his Ineffectual Sympathetic Villain minion DemiDevimon for petty reasons, and traveled to the real world in hopes of finding and murdering the eighth DigiDestined child, destroying much of Tokyo and killing several of his hench-mon along the way for the slightest failure; (he very seldom leaves a minion alive, in fact). After discovering that Gatomon was Kari's destined Digimon partner, Myotismon covered all of Odaiba in fog and launched an attack, kidnapping almost every family in the district and forcing Gatomon to identify which among the children of said families was her partner or he would kill them all, except then even when Kari was caught, he stated his plans to eat all the children later anyway. When Kari was finally brought before him, Myotismon attempted to kill her and ended up killing poor Wizardmon in the process. Any minions he hadn't already killed were eventually cannibalized to fuel his Super Mode, and he was stopped just in time to prevent the entire population of Odaiba from becoming his dessert. The entire time, Myotismon was motivated solely by undying hunger for power over both worlds.
    • Piedmon is a psychotic Monster Clown who doesn't give a damn about life at all so long as he has the power to step all over others with. As the leader and most powerful member of the Dark Masters, supreme leaders of all evil Digimon in the Digital World, he is fittingly the most vile member. He led the Dark Masters in all of their destructive acts, including wiping out Primary Village and all of its' Digi Eggs entirely (mass infanticide, pretty much) and warping the entire Digital World into Spiral Mountain. Early on he attempts to outright murder Mimi when her crying annoys him, and Chumon ends up Taking the Bullet and dying from being skewered instead. His entire reason for saving himself for last was to enjoy seeing the Digidestined be tormented by his fellow Dark Masters and their minions, and when they finally face him down, he savagely beats down their Digimon partners before turning the Digimon and children into keychain dolls for him to toy with; the entire sequence where he hunts down the kids and their Digimon one by one before transforming them, all while laughing with sadistic glee and mocking the two youngest team members (who he saves for last) is surprisingly tense and scary. But then he actually gets worse! He corners TK and Kari on a rope high above Spiral Mountain. Does he try to kill them with his swords? Nope. Try to turn them into keychains like their friends? Nope. He cuts the rope and sends them plummeting to the ground far below, laughing about it all the way! What makes Piedmon so horrible is that he's positively giddy about murdering children or confining their souls to a Fate Worse Than Death purely for his own amusement.
    • Machinedramon also counts. Most Killer Robots are unfeeling killing machines, and Machinedramon's Creepy Monotone would imply this applies to him too. But it's the things he actually says that show his true colors: his every word shows he's a cold, calculating sadist who loves killing people, and according to Piedmon, he lives only to destroy. He lent his machine army to Piedmon for his slaughter of the digital guardians in their castle when he went to steal the tags and crests, and his army also wiped out the Otamamon and Gekkomon kingdom, leaving few survivors. When the Digidestined are in his territory, he rigs the city with death traps in attempts to kill them, kills his own henchmen when he deems them no longer useful, and massacres an entire hoard of Numemon when they attempt to protect Kari from him. The most chilling line he has in the entire show is telling Kari, a little girl and one of the youngest Digidestined, that he is going to kill her in the most painful way he possibly can.
  • Crowning Music of Awesome: Best use of El Boléro de Ravel. EVER.
  • Ear Worm: "Digimon! Digital Monsters! Digimon are the champions!"
    • "Hey Digimon! Hey Digimon! Champions of the Digital World!"
  • Ensemble Darkhorse: Wizardmon, by far.
    • To elaborate on just how much Wizardmon was loved by the fans, one must see all the artwork the Digimon fans made of him and Gatomon together. Oh, and artwork of him in general. Not just that, but some even entered him and his badassery in online "versus" debates, contests and stories, pitting him against the likes of Mewtwo, Skeletor, Optimus Prime, Captain Planet and so on...
    • Piximon (at least in Latino America) Pi. It was as if a Furbill swallowed a cherube. With a small lance. Pi. He was also an very powerful and wise digimon that acted as a sort of Obi-wan for the Chosen ones. Pi. But it was his death scene against the Dark Masters to save the Chosen Children that cemented his eternal badassery with the Fanbase. Pi.
    • Machinedramon has the least screen time of the Dark Masters but has the largest fanbase thanks to his intimidating presence, voice (in both the original and the dub).
  • Epileptic Trees: Some fans speculate that Myotismon is actually Devimon, who was reborn after his defeat in File Island due to fact that Myotismon is an evolution of Devimon and that Myotismon seems very obsessed with Digi Destined, which would make sense if Myotismon was actually Devimon who sought revenge against them and it would make more meaningful if The Big Bad of Digimon Adventure 02 was their very first enemy.
  • Evil Is Sexy: LadyDevimon. Also, Myotismon, who easily seduced women as a lure to suck out their blood.
  • Fan Nickname: Koushirou/Izzy's laptop is quite obviously an iBook with the apples and logos replaced with pineapples, leading to the common fan nickname of "PiBook".
  • First Installment Wins: Many longtime Digimon fans see this as the season with the most creativity and originality.
  • Freud Was Right: VenomMyotismonmon's death.
  • Growing the Beard: While the Devimon and Etemon storylines contain some good, mindless fun (especially Etemon, who is delightfully silly), most fans agree that the series, along with the entire franchise, didn't really come into its own until Myotismon burst onto camera for the first time, with the far longer and more epic plot arc around him taking the show in a completely different direction than other Mons shows (and into places most "kids" shows never dared to go).
    • Arguably the dub as well. Early on it was in pure Gag Dub territory, but by the end it kept the vast majority of the serious moments serious and allowed for plenty of character development.
  • Hilarious in Hindsight:
    • When the DigiDestined are on the subway, they fall asleep, miss their stop, and end up in Shinjuku, where Digimon Tamers takes place.
    • Izzy's "alien theory" just got funnier with the rise of the Ancient Aliens meme.
  • Ho Yay: Tai and Matt to the fangirls, Izzy and Tentomon to their voice actors.
  • Magnificent Bastard:
    • Devimon, as the first ever Big Bad, was behind all Black Gears and traps set for the children on File Island. Whenever something didn't go his way, Devimon rolled with the punches and took the next best option, nearly succeeding at killing the kids and their Digimon multiple times, and rarely losing his composure, even while dying! Not to mention that he was probably the only Digimon villain who had some sanity in him, except the whole "plotting worldwide conquest" thing.
    • Meanwhile, Myotismon's entire scheme for traveling to the Real World is a gambit to kill the Eighth Child before she can fulfill her destiny and defeat him. Well in advance as he was readying for it, he ensnared the separated DigiDestined into traps that would have kept them in the Digital World and prevented their crests from glowing to make their Digimon partners stronger were it not for Sora and Biyomon acting as a Spanner in the Works and his lackey DemiDevimon's ineptitude. When he finally faces the DigiDestined himself when they're at a vulnerable point, he dominates the fight and was all set to kill them all prior to Garudamon fighting him to a standstill. After arriving in the Real World, he distributes mock Crests to his minions so that they can tell when they're near the Eighth Child, and when this fails he uses that child's destined partner Digimon, his own minion Gatomon, to pick out the child for him (all while keeping the Digivice and Crest safely far away). He is even charming enough to beguile human women so he can drink their blood in a weirdly sexual way, savvy enough to use his best techniques to his fullest advantage, and his plans are shrewd enough to be frighteningly competent, to the point of planning a backdoor from his own death!
  • Moe: Kari.
  • Nightmare Fuel: Piedmon's, ah, "keychain hobby", and Gatomon's life under Myotismon, and Wizardmon getting shredded by Myotismon, even in the edited version, and...well, needless to say, for a "kid's show" this sure got dark at times. That so much of it got past the censors is rather impressive.
    • Definitely qualifies. That episode literally gave me a nightmare. (A rather tame one, but a scary dream nonetheless.)
    • The pentultimate episode, when Apocalymon pretty much deleted the Digidestined and their partners. That's got to be pretty traumatizing for a kid watching the show...
    • Puppetmon.
    • Myotismon in general. Venom Myotismon is even more due to his...eating habits...
    • Machinedramon. The combination of his Creepy Monotone and the fact most of his dialog is composed of how much he enjoys killing people makes him one of the scariest villains in the show.
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  Machinedramon: Just what I was looking for, victims!

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  • Ship-to-Ship Combat: Tai/Sora fanboys/fangirls are notorious for this, as Digimon Adventure 02 has an epilogue wherein it's shown that Sora hooks up with Matt in the future, and most of them can't stand the thought.
    • It goes both ways, Sorato fanboys/fangirls are just as easily notorious for this.
      • For some reason in recent years, their seems to be a growing rift between Koumi and Jyoumi fans.
  • The Untwist: The search for the eighth Digidestined child plotline would've been more suspenseful, had the series not done the episode of Tai warping back to Earth, and realizing his sister knows a lot about the Digital World. Even worse, the end of that episode lampshaded Kari eventually joining up with the heroes. You'd have to completely skip that episode to be surprised by the outcome, and even then, probably not. At least the plotline still managed to be awesome, regardless.
  • Toy Ship: TK and Kari. Helped along by the relationship that their Digimon share.
    • Piedmon ships them. Seriously.
  • The Woobie: All the kids have their moments of being Woobies, but Matt and Izzy stand out.
    • Gatomon. Her life with Myotismon makes it impossible not to feel bad for the poor girl. Then Wizardmon's death and seeing her break down and cry.
  • Woolseyism: Some believe the added humor in the dub made the show even funnier, especially considering the dubbing company's past productions.