The Digital World's most Magnificent Bastards, Digimon and human alike, can be found here.
"Let's go, Let's go, Digital World!"
- Devimon and Myotismon from Digimon Adventure could be the first ever contenders for this trope in the franchise.
- 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. Even in death, he still pulls some strings behind the scenes; by appearing before the Digimon Emperor he played on Ken's superiority complex into making him use some of his own data to create Kimeramon and so, Devimon gained control over Kimeramon and would gladly use it against the Digidestined and the Emperor.
- 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! And this is just the first series!
- In the second movie, "Our War Game", Diaboromon's mad search and hunger for data earns the attention of Gennai and the DigiDestined. Assaulted as a Keraman by Tai, Izzy, and their Digimon, he tricks the latter two by jumping from Rookie to his Ultimate Form, Infermon, and subsequently overpowers them. Earning his first victory by attacking them mid-transformation, Infermon escapes and covers his tracks by clogging up the dial-up phone lines. When Izzy uses a satellite uplink to continue the pursuit, Diaboromon hijacks the connection to send missiles to Colorado and Japan to put them on the clock. Multiplying himself to hide the real one to kill time, it takes the might of Omnimon to destroy them all. Although Diaboromon resorts to outspeeding them, he's eventually caught and defeated. Returning in the sequel, he orchestrates his revival by tricking the DigiDestined into opening gates for his Kuramon swarms. Diaboromon holds out against his old foe Omnimon in the Digital World, showing how much he learned, before successfully digivolving into Armageddemon in the real world. Boasting a mere two appearances, Diaboromon regardless managed to be one of the DigiDestined's most cunning, adaptable, and dangerous adversaries.
- Yukio Oikawa from Digimon Adventure 02 masterminded pretty much behind everything that happened in the series, and he started it all with just a simple e-mail he sent to Ken Ichijouji, a young boy wretched with guilt over his brother's death that he blamed himself for, which tells him to use the digivice he found some time ago to travel into another world. Little Ken does so and ends up in the Dark Ocean, a world of darkness and negativity which corrupts Ken into the evil Digimon Emperor. Now with Ken as his unknowing pawn, he uses him to conquer the Digital World and set up Control Spires, obelisk towers of darkness used to weaken the Digital World's defences and, in the long term, the border between the Digital World and the Real World. However, when the Digidestined defeats Ken and cleans the Digital World of the spires, Oikawa sends his agents Arukenimon and Mummymon to kill them by transforming the spires into monsters, and to destroy the Destiny Stones in order to hasten the weakening of the border. With enough Destiny Stones destroyed, the border becomes so weak that Digimon invade the Real World in thousends, and with that as a convient diversion, Oikawa moves on to his next step. He and his minions recruits some lonely kids with promises of power and talents and then kidnaps Ken, copies the Dark Spore that was planted inside him, and transplats the copies inside the children. With time, those copies would grow into something so powerful that it would give Oikawa the final crack on the border he needed to enter the Digital World and claim it as his own. A simple goal which required complicated tactics and difficult planning to reach, and yet Oikawa pulled it all off like it was no problem at all. But then unfortunately for Oikawa, it's revealed that he was just a pawn of Myotismon all along, and that Myotismon is the true Chessmaster of Adventure 02.
- Digimon Frontier:
- Ostensibly the leader of the evil Legendary Warriors, Mercurymon is the scheming Warrior of Steel prepared to undermine his own leader Cherubimon and allies for personal gain. Straying to the background to let his comrades do all the grunt work, Mercurymon seizes the chance to defeat Seraphimon in a single, bold Dark Reflection and steal his data for himself. Later, he uses his Beast form Sakkakumon to pit both heroes and villains against one another allowing him to copy their powers even when ShadowSeraphimon is defeated. Enough of a suave snarker to play Ranamon's jealousy to his advantage, Mercurymon was ultimately only undone when the heroes unexpectedly overcame his own Thanatos Gambit. Ever prepared to construct grandiose spectacle and speak in that slick Shakespearean accent, Mercurymon was one of the most competent villains in the anime.
- Murmukusmon is main antagonist of the movie. Arriving to the Island of Lost Digimon long ago, Murmukusmon obscured an ancient tablet about Ornismon to trick the populace into revering the monster as a benevolent legend. Posing as d'Arcmon and Hippogriffomon, leaders of the Human and Beast Digimon respectively, he strokes constant civil war through powerful rhetoric, convincingly feigned emotion, and appeal to their pain, causing many allies from all sides to revert into Digi-Eggs, and thus excess Digi Code, when defeated. By the time the Legendary Warriors discover his ruse, Murmukusmon acquires all the code he needed, reveals his deception and the true history, and initiates Ornsimon's revival. Cold and calculating, Murmukusmon played everyone for fools and schemed to conquer the Digital World with his new living superweapon.
- Digimon Savers: Nanami is a member of the Bio-Hybrid, a trio under the subservience of Akihiro Kurata. A genius who grew up isolated from everyone because of her prodigious intelligence, Nanami joined Kurata and hunted Digimon solely as an outlet to escape the droll in her life. Taking an interest in Thomas H. Norstein, Nanami undercuts his plan to protect the waterfall of the Sacred City located on ElDradimon by easily guessing where he'd be. Spending the entire scuffle against him and Gaomon predicting their every move with utter ease and mysterious grace, Nanami uses their shared experiences and her own dark charms to try and shake Thomas's faith in his friends. While undone by Thomas using a strategy unfathomable to both her and MirageGaogamon, Nanami still has the last laugh, gracefully accepting defeat only because she pushed Thomas into using someone else's power and tactics rather than his own, and uprooting Thomas's strategy by destroying the coveted waterfall.
- Digimon Fusion:
- The anime version has AxeKnightmon, whose magnificence is aided by being as Badass as his name would suggest. He spends years manipulating a meek Child Prodigy into thinking that the Digital World is a game where no one can die so that he'll willingly work for him and grant him access to DigiXros, then blackmails his sister into helping him too by using him as a hostage, neither aware of the other's true situation. While he is a servant (and younger brother) of the Big Bad, Bagramon, he poses as the leader of a rival faction for much of the series, and even spies on and sabotages the plans of the Quirky Miniboss Squad (partly to keep up the charade, partly to make himself look better, but mostly because it's hilarious). And in the end it turns out he really was working against Bagramon - he encouraged the protagonists to get stronger so that they would be around to attack Bagramon while he was focusing most of his power into his doomsday technique, allowing AxeKnightmon to stab him in the back while he's distracted and absorb him. Holding himself with an air of gentlemanly confidence even as he schemes, AxeKnightmon cemented himself as one of the most memorable strategists in the war.
- Bagramon, better known as Lord Bagra, is The Emperor of the Bagra Empire and general of the selfsame army who desires to erase the imperfections of the worlds. Commanding the Seven Death Generals and their minions, he placed everyone in such a position where, in victory or defeat, he would acquire the negative energy necessary to start D5 in hopes of remaking both the Human and Digital World In Their Own Image. As the older brother of AxeKnightmon, he suspected his sibling's treachery since the very beginning but played along even after being backstabbed. Congratulating and critiquing AxeKnightmon in the same sentence, Lord Bagra reclaims his title as the ultimate enemy by turning the absorption around from the inside out and remanifesting as DarknessBagramon. Giving the Fusion Fighters one of the hardest-earned victories in the franchise, Lord Bagra proved his dreaded strength.
- The manga's version of Bagramon also qualifies. Rebelling against Homeostasis because of her plan to have Digimon branded as heroic or villainous, in a system that would result in his brother's death, Bagramon is defeated and exiled. Finding the remains of the digital deity Ygdrassil, Bagramon uses them to empower himself and begin his conquest, creating the Xros Loader and the powerful artificial Digimon Tactimon. He then rebels again with the loyalty of dark Digimons, defeating the Royal Knights and breaking the digital world. Manipulating his brother using two minions and some humans, Bagramon intends to judge humans and Digimons based on who wins between them. When his brother "wins" while losing his sanity, Bagramon cries for him before using him to recreate Zeed Milleniunmon, intending to use it to euthanize both the digital and human worlds and save them from decay. When he is proven wrong by the heroes, Bagramon cheers for them and dies saving his brother, encouraging him to be better.
- Tactimon in the manga is also far more honorable and intelligent than his anime counterpart. Leading his armies in the fractured Digital World, Bagramon is the digimon that broke it during his fight against the powerful Royal Knight Omegamon. A ruthless yet effective general willing to fire against his own soldiers in harsh fights, Bagramon also prefers to not waste their lives in pointless battles. Manipulating Mach Leomon to his death to test the power of his rivals, Tactimon follows the heroes to test their power as well. During the final battle of the Bagra Army, Tactimon asks permission to use his full power and challenge the heroes in a harsh fight, showing his impressive unmatched skill and only being defeated by their determination and teamwork. Lethally wounded, congratulates them, happy at having find worthy opponents.
- Lucemon, leader of the Seven Great Demon Lords who embodies the sin of Pride, frequently walks the fine line between this trope and a Smug Snake in his various appearances throughout the franchise. His appearance in Fusion is particularly magnificent; a citizen of the Heaven Zone, Lucemon campaigns to be elected the Zone's next leader who, if elected, would embrace love and mercy as a policy as contrast to GuardiAngemon's extreme justice. When the Fusion Fighters are wrongfully accused of a crime and threatened with execution, Lucemon pleads for clemency to both them and the real culprit, Cupimon, and voices the importance of allowing citizens to speak for themselves, getting him popular support among those in the Heaven Zone. But once he's won and is to be crowned, he returns to his true self - an ally to the Bagra Empire and fellow Demon Lord Laylamon - and rips the zone in two, revealing the temple that holds the Code Crown and trapping it in a giant sphere of darkness. Even when it looks like Lucemon has been beaten, he survives the attack and returns to kidnap Nene just as she's transmitting the dark sphere's power to AxeKnightmon, making him an unexpected thorn in even AxeKnightmon's side.
- Digimon Universe: App Monsters features the following two incarnations of Leviathan:
- Anime: Leviathan is the "Final Boss AI" sealed in within the Dark Web of the Net Ocean, the founder of L Corp who allows C.E.O Knight to operate under his direction, and the orchestrator of all events within the plot. Separating himself from Minerva, Leviathan sought to fulfill his directive of guiding humanity through the "Human Applification Project," where he planned to turn all of the Human World into Apps to remove all conflict and suffering at cost of free will. Once the extent of Leviathan's strategies are revealed, he has shown to be one step ahead of the heroes at all times, factoring in their growth to his ultimate plan and managing to keep tabs of their developments. After one last Sadistic Choice in hopes of keeping his dream alive, Leviathan is so impressed by the actions therein that he takes his deletion with grace, wishing humanity "good luck."
- Manga: Leviathan is the leader and founder of the L Corp who seeks the fulfillment of the "Human Applification Project" alongside her partner, Knight Unryūji. Masterminding every conflict through her L-Virus and putting her henchmen in the positions to apprehend the Seven Code Appmon meant to stop her, Leviathan ultimately manifests via possession of the powerful Deusmon to force a hard-fought battle for the worlds. After being defeated and shown the strength of the bonds between Humans and Appmon, Leviathan seemingly joins Haru with Minerva, showing a willingness to be swayed from her strong ideals.
- The franchise's greatest example would be Millenniummon, since unlike all the others he ultimately achieved what it wanted: to become Ryo's Partner even though he would have also liked to start conquering the Multiverse immediately (note that he can wait for it anyway). His actions led to nearly everything that went wrong with Digimon Adventure and Digimon Adventure 02 (including those of the ones mentioned above), but because he managed to remain undetected and completely out of reach he became The Unfought. He also succeeded in creating himself without being noticed by an omniscient being. Details can be found in the series synopsis page.