Digimon Adventure/YMMV

"Machinedramon: Just what I was looking for, victims!"
 * 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.
 * That definitely blew up in his face.
 * Complete Monster: Myotismon and Piedmon.
 * Special mention goes to Myotismon. The main reason is he's unmatched in sheer sadism (except the ones below) by any other enemy. His entire arc is pretty much one long string of Moral Event Horizons and he murders most of his henchmen in cold blood. Really driven home when Angemon and Angewomon outright ask him if he feels one ounce of guilt over his actions and he replies with a resounding no. There's a good reason that until Digimon Savers, he was considered the most evil Digimon villain ever (he ends up getting killed three times, more or less possibly because of this).
 * Piedmon should be explained as well. As the leader and most powerful member of the Dark Masters, supreme leaders of all evil digimon, 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 (baby killing, pretty much.) His entire reason for saving himself for last was to enjoy seeing the Digidestined be tormented by his fellow Dark Masters and then his minions. He then proceeds to hunt down the Digidestined and their Digimon, turning them into keychains one by one and then taunting the remaining ones with them! But he gets worse! He corners TK and Kari on a rope high above Spiral Mountain and cuts off their only route of escape. 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 and laughs about it! What makes him so bad is that he's positively giddy about murdering children or confining them to an And I Must Scream fate. His ultimate fate (going inside MagnaAngemon's Gate of Destiny) is one that he well-deserves. Arguably he is just as bad as Myotismon.
 * Machinedramon, while less so than Myotismon and Piedmon (mainly due to much less screentime) also qualifies. Just listen to the things he says, unlike most Killer Robots, he actually likes killing people. MetalSeadramon was more "just business" and Puppetmon was at least a little sympathetic, but Machinedramon was a cold, calculating sadist. Probably the creepiest line he has is when Kari starts towards him, he tells her he'll make her death as painful as he possibly can. She's a little girl and he outright said he'd kill her in the most painful way he possibly could, despite the fact she doesn't seem like a threat to him at all. He's also has the highest onscreen death count of any of the Dark Masters, killing an entire swarm of Numamon like thay're nothing but flies. One can't help but think he'd have leveled the city to find the Digidestined whether it was abandoned or not. Suffice to say, watching him getting sliced in half is quite entertaining.
 * Apocalymon, the true Big Bad, may qualify for this trope. Although he came out of nowhere, was rather Laughably Evil Large Ham in the dub and didn't have much screen time and lacked huge amount of characterization, he is still the cause for all chaos and trouble in Digital World, is the master of Dark Masters and his mere prensence caused chaos and his goal is to twist both Digital World and Real World in his image. Also in Digimon Wonder Swan Series it is stated that Apocalymon's existence brought Dark Masters, Devimon and Myotismon into existence, meaning that he is responsible for creation of three complete monsters (Myotismon, Machinedramon and Piedmon) and is indirectly responsible for.
 * Crowning Music of Awesome: Best use of El Boléro de Ravel. EVER.
 * Butter-fly should rank high on most anime fans's list of most inspirational anime theme songs. Brave Heart pretty much defined what an "evolution" song should be like, and how it should be used: every time you heard it come up, you just knew a Crowning Moment of Awesome was just about to happen. In fact, if it's by Wada Kouji, it counts as Crowning Music, PERIOD.
 * Don't forget the opening theme for the dub, or the digivolution music. Hey, Digimon was also pretty good, if kind of a weird fit for fighting sequences.
 * Truly, its a sad, emotional moment when  MUGENDAI no yume no ato no nanimo nai yo no naka ja Sou sa itoshii omoi mo makesou ni naru kedo Stay shigachi na imeeji darake no tayorinai tsubasa demo Kitto toberu sa oh yeah . In solo voice. With a small chorus. For this troper who was 12 at the time, it was the most awesome thing 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.
 * 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
 * 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 was behind all Black Gears and traps set for the children on File Island and rarely lost his composure, even while dying!
 * Not to mention that he was probably the only Digimon villain who had some sanity in him, except the conquest thing..
 * 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. He distributes mock crests to his minions so that they can tell when they're near the chosen child, and when that fails, he uses that child's potential partner to pick out the child for him (all while keeping the digivice and crest safely far away). He is charming enough to beguile human women so he can drink their blood in a weirdly sexual way, and his plans are shrewd enough to be frighteningly competent. And this is just the first season!
 * Moe: Kari.
 * Nightmare Fuel: Piedmon's, ah, "keychain hobby", and Gatomon's life under Myotismon, and Wizardmon, 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  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.


 * Back to Piedmon's "hobby", what makes even scarier is his hunting them down one by one in a methodical and sadistic manner. Except for the fact he doesn't actually kill them, it's almost like watching a slasher killer hunting down his victims one by one...
 * Tokomon's teeth.
 * Two Words: forced Digivolution. The fact the Transformation Sequence just didn't feel right didn't help toning down the audience's reactions.
 * Ship to Ship Combat: Tai/Sora fanboys/fangirls are notorious for this, as, 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.
 * Tear Jerker: The ending of the series. *sniffs*
 * Gatomon's flashback to her life with Myotismon...
 * Not to mention.
 * Tai's moment concerning his Big Brother Instinct for Kari in 48.
 * 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.
 * Woolseyism: Some believe the added humor in the dub made the show even funnier, especially considering the dubbing company's past productions.