Kuyo and his student police force, who beat up the Unwanted Harem and actually killed Tsukune; this was the first time he was injected with blood.
Ruby's master helped the transition along, in an arc that focused heavily on Fantastic Racism, which has since become one of the series' most prevalent themes. She was planning to wage war on humanity, and was willing to cut down her own adopted daughter to do so!
Midou and the outcast monsters, who beat up Inner Moka, killed Tsukune again, and caused this next blood injection to put the Evil in Superpowered Evil Side. After this incident, the main theme of Fantastic Racism between humans and monsters, and between monsters and other monsters, really began to take over.
Legato from Trigun. See his entry under Gut Punch for more detail.
Monev follows Legato's cue and begins shortly afterwards - while previously Vash was always able to stop the villains before they can do serious harm, the guy basically moves down everyone in his path (including women and children) to get his target - and he actually enjoys this collateral damage. This is also the first time that Vash really loses it, and comes close to killing Monev.
The first one is Udo Jin-e. The series had started rather lightly... and in came this loudBlood Knight with a permanent Slasher Smile, an until-then-unseen degree of cruelty, the capacity of either killing you bloodily or put you in an And I Must Scream position, and the dubious "honor" of showing us some glimpses of what would happen if Kenshin ever fully reverted to his Battousai side.
The second is Saitou Hajime. His introduction signaled the arrival of the Kyoto Arc (and the much more dangerous villain Shishio) whereas previously, the series had been a light-hearted action comedy where, a few serious villains like the aforementioned Jin'e and Aoshi aside, Kenshin's everyday life continued as a light-hearted and comical romp.
Kurata from Digimon Savers is the perfect example of this trope. Before he had appeared the only real "dark" parts of the anime resulted from Gotsumon's incredibly hostile attitude toward Ikuto/Keenan. When Kurata arrived, he brought genocide (including the deaths of both of Ikuto/Keenan's "parents", resulting in genuine Tear Jerker scenes) and singlehandedly made the season the darkest one yet. For once we had a genuinely evil human, and also BY FAR the most evil character ever to grace the franchise.
Devimon in the original Digimon Adventure. While the first few episodes of the show were simple Monster of the Week, his appearance in Episode 8 introduced a proper, intertwined story arc and highlighted that the show wasn't kidding around anymore. It got somewhat lighter - though with even more Myth Arc - in the short 'Etemon arc' - only for Myotismon to firmly seal the series in Cerebus Syndrome.
Whenever Medusa or Asura show up in Soul Eater, things stop being wacky and people start dying and going insane.
Zophise from Gash Bell. Gash Bell tends to get a lot of these, because most of the enemies tend to be fairly goofy, it's jarring when you get someone who's playing for keeps.
Raditz in DBZ, who jumped the series out of being comedy-focused altogether.
General Rildo in Dragon Ball GT; until he showed up, GT was a throwback to the comedy of early DB.
Mazinger Z has a weird example in Count Brocken. To put it simply, he is the first villain to harm(and actually killed) innocent people. And from that, he proceed to do some horrible stuff. He is so notable amongst the villains that in fact, right in this wiki, he is the most notable person that is mentioned when the Dark part of Mazinger Z is talked about, complete with arguably creepier design than the already creepy Ashura and the show indeed goes into the darker parts after this. The weird part ? at the same chapter he appeared, he provided the single most hilarious moments in the entire series in a rather stupid way. Its kinda hard to think hes the same person who killed person on the screen for the first time.
Fate Averruncus from the Mahou Sensei Negima! manga. His first appearance saw him petrifying a bunch of people and essentially defeating the party (who had been putting up a good fight up to that point) all on his own. When he appeared a second time he averted Bloodless Carnage by impaling Negi with a hunk of stone and scattering everyone across the world. This was the trigger that eventually led Negi to begin using Black Magic. Oh, and Fate's ultimate goal is to erase the magic world from existence, along with everyone in it.
Arguably, Evangeline serves as an earlier example. Once it's revealed that not only is she a vampire with a Power Limiter curse that also binds her to the school, but the one who cursed her was Negi's father, and she needs Negi's blood to break it, the series started its Genre Shift from harem comedy to shonen.
At least until Jail, in the third season, mentioned that he had all of the Numbers (functionally, and sometimes biologically, his daughters) impregnated with clones of himself. Yeah...
The Huckebein from FORCE are taking the series to a new level of dark.
Mukuro Rokudo from Katekyo Hitman Reborn! is an example of this trope; in the beginning of his story arc, a number of major characters are badly beaten. His appearance also signals a major Genre Shift in the series, which had been comedic until this point.
Makubex in Get Backers. Before the IL recovery mission, Ban and Ginji were retrieving things like expensive melons and a blind girl's violin. Makubex threatened them with an atomic bomb!
Then came the true arms of Venus and all that, but Makubex was the first to give them a real battle.
Takasugi Shinsuke in Gintama is the first seriously evil character, and is featured in the series' first serious arc, benizakura. He is probably also the only main character in the show who doesn't have comedic side.
Unless he's hiding something behind that cute face and mindless violence, Kamui counts.
Though Tsutomu Nihei's Blame!! was never what you'd call light-hearted, the appearance of The Safeguard marked a dramatic shift in the storyline to something much more epic.
Pantyhose Tarou was only the first of a succession of very serious, very powerful foes in Ranma ½: while earlier opponents were always ineffectual antagonists versed in wacky, fun, harmless Martial Arts and Crafts tournaments, Ryugenzawa's Orochi, Prince Herb of the Musk Dynasty, Ryuu Kumon, and The PhoenixKingSaffron followed in Pantyhose Taro's footsteps by forcing Ranma & Co. into more serious, no-nonsense combat, where death was suddenly a very real possibility.
It should be noted, however, that Ranma ˝ doesn't have overarching plots and the "Cerebus Syndrome" brought about by those characters only lasted for their specific story arcs, being more or less forgotten about once their arc is over (not to mention that their arcs aren't entirely joke free either).
In fact, Tarou is actually the least "Grim Dark" of the series' Knights of Cerebus, as while a ruthless, formidable fighter, Tarou's stories also tend to be full of the usual goofiness and just plain ridiculous happenings. In his first story, the whole mess is over getting his name changed, while his last story has him battling a fellow lucky Jusenkyo victim over back-pain relieving magnets, which he ends up believing will give him the power to Take Over the World.
Gundam ZZ started out almost ridiculously lighthearted but after a bunch of Ineffectual Sympathetic Villains, Haman Karn gets into the plot and all of a sudden the heroes really need to worry.
Another Gundam example would be G Gundam though only the first few episodes are rather easy going until Devil Gundam and Kyouji are first mentioned.
It's still relatively easygoing even after the introduction of Kyouji and the Devil Gundam, but then Master Asia (or, more specifically, his Face Heel Turn and the Broken Pedestal that comes with it) jumps into the story...
Depending on if we're talking about the manga or the anime of Rozen Maiden, either Barasuishou or Kirakishou counts. It should be noted in Kirakishou's case that when the most cheerful and childlike character in the whole franchise gets eaten by her, you know there won't be much more comedy. Barasuishou on the other hand both directly and indirectly causes the deaths of all the other characters deliberately just to please her father, Enju, a jealous apprentice to Rozen, and with her dead serious attitude that everybody must participate in the Alice Game, it is not very surprising.
Butch and Cassidy of Pokémon be headed for this at their first appearance, being a Terrible Trio in their own right with a crooked Officer Jenny. It...didn'tlastlong, but at least other members of Team Rocket manage to stay properly intimidating — especially when they show up in force. Even Max admits that the cast is pretty lucky that they usually only have to deal with the Terrible Trio that stalks them around.
Pokémon Hunter J easily surpasses them in malevolence, being the darkest villain to ever appear in the series and to never suffer from Villain Decay, not to mention being one of the few characters that was actually killed off. While technically not a villain, Paul seems headed this way, being more abusive towards his Pokémon than anyone else.
Another good example is Sabrina, who popped up MUCH earlier than Butch and Cassidy and WAY before J did. Sabrina only appeared for three episodes, and after her arc everything returned for normal, but for years later, no villain surpassed Sabrina in terms of scariness*
Even though Sabrina was closer to a Woobie, Destroyer of Worlds, as it is implied that she was incapable of controlling her psychic powers before Haunter came along
. Let's face it: she transformed trainers she defeated into dolls, and was just plain creepy. J may be more evil and has no qualms committing murder, but at least she doesn't turn people into dolls!
Combining this with Not-So-Harmless Villain is the Team Rocket trio themselves in the Best Wishes series.
Cyrus of Team Galactic intended to destroy the entire world and everyone with it (even the other members of Team Galactic) while possessing Azelf, Mesprit, Uxie, Dialga, and Palkia to create a new dimension for him to rule. And he apparently dies in the episode right after J.
Dr. Yung in The Mastermind of Mirage Pokemon tortures Pikachu, and was previously expelled for his twisted experiments. And after his defeat he runs into his burning lab and is presumably incinerated.
N, Ghetsis, Colress, and Team Plasma in Best Wishes 2 Episode N.
Yami Marik in Yu-Gi-Oh!. Contrary to the original Marik he was not content to hide in the shadows relying on minions and trickery, he would personally duel and make his opponents writhe in pain in the Shadow Games he inflicts on them. In both the original Japanese and the English dub, Marik was focused on Yami Yugi and only saw his friends as pawns to be used to get to him. Yami Marik on the other hand didn't care who he faced, he would make them suffer and eventually Mind Rape them when they lost. He also underwent an Evil Costume Switch, trading in Marik's Bare Your Midriff pink shirt for a sleeveless black one with a Badass Cape, the Eye of Ra was permanently displayed on his forhead, his hair was suddenly spiking into the air, and his voice is deeper with an echo effect.
The Three Tenors in Yu-Gi-Oh! 5Ds. While the full extent of their plan isn't revealed for some time, when they first began to appear they rolled out the Meklord archtype and sent Yusei into a Heroic BSOD when suddenly the iconic Synchro monsters of the series that almost all the duelists rely on became useless, forcing them to re-evaluate their strategies in addition to the mystery of the new villains that had rolled into town.
Evangelion was a dark series to begin with, but the events of the "Action Arc" (from Asuka's arrival up to Leliel/Twelfth Angel) were relatively light-hearted, with Misato and Kaji seemingly making amends, and Shinji starting to gain some confidence. ...Then came Bardiel/The Thirteenth Angel, and everything went to Hell, culminating in End of Evangelion.
Rebuild of Evangelion 2.0 is, for most of its running time, a much Lighter and Softer story than the episodes it's adapting. There's a good amount of comedy, we see the kids bonding, Asuka's less of a Jerkass, and the angel battles ("Clockiel" and Sahaquiel) are focused more on awesomeness. Then Bardiel shows up and possesses Unit-03 with Asuka inside, and the movie goes straight into Nightmare Fuel territory.
Medaka Box once was a lighthearted, comedic series about school adventures of a God Mode Sue and her harem. After 14 chapters of that, the first serious antagonist, Unzen Myouri appeared, heralding oncoming Genre Shift into a fighting series with a brutal bloodbath (no one supposedly died, but a ton of people probably were put in hospital for years). And just as the arc, started by Unzen's appearance was about to end, Kumagawa Misogi stepped on the scene, signaling a lesser shift to even more Darker and Edgier tone.
Chirin No Suzu was all cute and adorable until the Wolf appeared and the mood became very dark.
Puella Magi Madoka Magica looked like it was going to be another typical magical girl show, albeit one with unusually dark undertones. Then came Episode 3, which introduced Charlotte, the third Witch. The moment when she ate fan favorite and Cool Big Sis Mami alive was the moment when the series showed just how dark of a Deconstruction of the genre that it could be. And this was only a taste of what would come later.
Unusually for this trope, Charlotte is defeated shortly after she killed Mami.
The Spin-Off manga Puella Magi Kazumi Magica has Yuuri. Another unusual example because she only took the role in the fourth chapter, having appeared as a Mysterious Watcher in the first two and an easily defeated antagonist in the third. But in the fourth, hoo boy...
Claymore never made any pretenses to be anything other than a dark series, but whenever Priscilla turns up, things are going to go south very, VERY fast.
Mag Mel from Bakugan. Previous villains were dark, but Mag Mel is by far the most terrifying villain yet with an extremely dark storyline. He was imprisoned for genocide and that's before the series even started! Once he appeared, he Mind Raped Dan and Drago in a very horrific manner. Once he was finally free, he started trying to burn Gundelia to the ground. In scope of sheer evil and darkness, he's the darkest and most horrifying villain in the entire series!
The first is Aizen Sousuke. In the Arrancar Arc, there's relatively little comic relief compared to the last two. And the man has no sense of humor himself. His reaction to SEEING comic relief unfold is to wonder whether or not it's a bad strategy to take him off of his guard. Even before outing himself as a villain, Aizen was completely humorless. During an extended flashback, Shinji comments on how uptight he is.
Shukuro Tsukishima was this during the Xcution arc, though he did have a sense of humor.
In the "Thousand Year Blood War arc", the Vandenreich are this. The devastation they have brought to Soul Society within the span of only a few minutes was unprecedented in the story to that point and the leader is willing to sacrifice his own followers for even slight infractions. In a slight subversion, the guy's only shown interest in doing that if they are some of the Arrancar that he enslaved.
The entire first episode of Cube X Cursed X Curious seemed to be setting up for a lighthearted Slice of Life comedy series. Episode 2, enter: Peavey.
Higurashi No Naku Koro Ni seems like a light-hearted harem comedy until Miyo pops up and starts putting things in Keiichi's head.
Ooishi can tend to be this for specific arcs as well. When he shows up, you know Mood Whiplash is about to kick in. It even becomes a plot point in Tatarigoroshi-hen, in which Keiichi sees him as the personification of the end of their happy days.
Tiger & Bunny has several, each one putting the series deeper into much darker territory:
Lunatic - Vigilante Man, first to kill somebody in the series. Whenever he shows up, things starts turning grim. He has a Day in the Limelight in episode 16, probably the most depressing episode in the entire series.
Jake Martinez - while Lunatic was treated seriously, he was at least a Well-Intentioned Extremist, while Jake held the entire city hostage, and sent the main character and four of his friends to the hospitalFor the Evulz. He was the first villain who was shown to take pleasure in evildoing.
Doctor Rotwang and Cis from episode 15, who have been indirectly responsible for starting a chain of heartbreaking moments that prevailed through the rest of the series.
And finally the Big Bad Albert Maverick mindraping Barnaby in a scene strongly reminding of date-rape scenario, being the first to murder non-villainous cast member and framing Kotetsu for it.
SpaceMonsters from Gunbuster - for the first two episodes series is lighthearted and funny, being basically sport story with mechas and serious elements were nothing more but backstory. Once the first battle has come, it turned into desperate fight for survival and stayed that way even after the shift to the Super Robot Genre.
Diebuster starts as sympathetic and optimistic Super RobotMonster of the Week show, but after one of true Space Monsters, the same ones as in Gunbuster shows up, things go to hell very fast.
Phi Brain Kami No Puzzle played with this - new villain, Herbert Müller, didn't started the shift to more serious tone. In fact his appearance stopped one that was already taking place, by putting delay on plans of previously established villain Rook, who resumed them after Müller was out of picture and became Knight Of Cerebus himself.
It's interesting to watch the increase of the power of the villains in One Piece. Alvida and Morgan possessed no real threat to Luffy, and Buggy wasn't really much of a challenge either. Afterwards, Captain Kuro and Don Krieg were much more menacing, but still relatively weak: They were just bad guys who happened to show up at the time. Everything changed when Arlong came along, and while the series retained its light-hearted tone for the most part, seeing what the stakes are when a real monster gets involved changed the world of the series forever. Follow this up with an enemy Luffy can't fight in the form of Smoker, and it's clear that the end of the East Blue saga was when the series hit its' stride.
And then Crocodile, Nico Robin and the Alabasta arc up the ante, going from relatively minor conflicts to an all-out civil war. It also marks the point where the heroes start ending up on the verge of defeat (repeatedly) by an opponent far beyond their level, as well as expanding on the series' Myth Arc (becoming far more than Luffy searching for some buried treasure and becoming King of the Pirates.)
Admiral Akainu finally averts the "Nobody dies in One Piece outside of flashbacks" rule by killing Ace. Blackbeard follows it up soon after by killing Whitebeard and bringing about a new age of pirates.
Transformers: Beast Wars II is an incredibly light-hearted show with hilarious characters, that hardly ever takes itself seriously. And its villains are no exceptions - Galvatron - the Big Bad is a narcoleptic who spends most of the show asleep, leaving his inept kid brother Megastorm to run the show with an effeminate Dragon (Starscream), a thug who can only repeat his own name (BB), and Beavis and Butt-Head (Thrust and Dirge) under his command. Cue the last 10 episodes of the show, where Galvatron wakes up, takes command, and we learn that he has a gigantic Doomsday Device en route to Gaia, which he intends to use to destroy the whole planet and siphon the Anglomois energy. And then things go grimdark... Gigastorm (Megastorm after his makeover) is fatally wounded and dies in Galvatron's arms, and the whole series ends with all the Maximals sacrificing themselves to destroy the Nemesis, in the end flying up to 'robot heaven'. Granted, Beast Wars Neo retcons this.
In Naruto, although the first major villain, Zabuza, had already been introduced we saw the kids handling on their own against him with the help from their teacher, Kakashi; when Orochimaru is introduced, he is shown to be a villain that even the most experienced jounin fear and ends up killing the Third Hokage. Much later, the reveal of Pain serves as this since shortly after his introduction he kills Naruto's bumbling master, Jiraiya.
Much like it's Spiritual SuccessorClaymore, Berserk is nothing short of a Dark Fantasy series. However, the TV series is considerably Lighter and Softer than its manga counterpart, so for the majority of the TV series' run, it was basically composed of Guts and Griffith talking about dreams and ambition, the Hawks battling the Tudor Empire for the Kingdom of Midland and a bunch of political stuff, and developing characterization that wasn't derailed by Adaptation Induced Plotholes or Adaptation Explanation Extrication. But when Nosferatu Zodd was introduced with his prophecy halfway through the series, followed by the introduction of the Godhand toward the end especially the transformation of Griffith, we knew that this series was going to end on a bad note.
Tsubasa: RESERVoir CHRoNiCLE has a rather interesting example where this trope is actually a heroic character, (or at least a good guy). Confused? Halfway through the manga, it's revealed that the main character Syaoran is actually a clone of another "Syaoran" that The Big Bad had locked away. The Original "Syaoran" eventually manages to escape and gets warped to where the heroes are, but by that time, Clone Syaoran (known as "Cloney" by the fans) has reverted to a heartless automaton. Cloney becomes an antagonist while "Syaoran" becomes the new main character, and from then on, the manga is a hell of a lot darker than it was before.
The Metarex in Sonic X fit this trope really well. So basically, the first two seasons of the show were pretty much light-hearted and funny in tone. Then cue the arrival of the Metarex, a group of dangerous cyborgs and robots that plan to harness the power of the Planet Eggs to cause a plantation of the entire galaxy and wipe out all flesh and blood so plants can rule. The Metarex come in many different types of their own, like the one-shot villain Red Pine, the Laughably Evilbrute Yellow Zelkova, emotionless monsters like Pale Bay Leaf as well as Black Narcissus, who captured and tortured Chris and Cosmo and used them as bait to lure Sonic to him, and the tragically villainousMagnificent Bastard Dark Oak himself.
Fairy Tail has two. Jellal is the first villain who poses a serious threat to the cast's lives, and is trying to return Zeref himself, as opposed to the various demon Zeref created that have been sought out in earlier arcs, or power skirmishes that have otherwise been the focus. In adition, while previous tragic backstories have been about losing or fighting with family members, his and Erza's past is full of all kinds of slavery, torture, and betrayal. After Jellal every arc is some serious threat that will either kill the cast or destroy the country. The second is Hades, who is also the second villain to seek Zeref. He turns the first lighthearted arc in over 100 chapters into a fight for survival that ends with the series no longer being a Nobody Can Die story, many characters' sufferings to turn out to have been for no reason, Zeref potentially unleashed on the world, and he inadvertently summons an evil dragon that leaves the core cast Legally Dead for seven years. Zeref himself, oddly enough, has yet to invoke this trope.
In the Monster Rancher anime, General Durahan's arrival signaled the end of lighthearted episodes; he even appears right after a lighthearted one. He's also a literal knight.
Toriko was a light hearted food hunting series with the occasional creepy GT Robots, and the arc after them is another finding secret recipe mission much like prior to their appearances. then Tommyrod shows up. Unlike Starjun and Grinpatch, who were Noble Demon and Affably Evil villains respectively, Tommyrod kept all kinds of hideous parasitic insects within his body, who seriously tries to kill Toriko and actually manages to win the fight, despite getting an awesome asskicking, and from there the story gets much darker.
Starjun is a milder example, being no-nonscence and having a dark aura, and being the truly first time that Toriko comes close to death.
Code Geass is by no means a light show, but it still has its breather moments. Except, for one, whenever V.V. meddles, invariably causing things to get worse.
By the time Deep Blue finally steps out of the shadows in Tokyo Mew Mew, things start taking a turn for the darker and more dramatic for the Mew Mews.
Vicious from Cowboy Bebop. Not only is he the main antagonist in five of the 26 episodes he's in, he's also a major threat to Spike.
One Piece usually has a strange Sorting Algorithm of Evil with its Big Bad bosses, ranging from dangerously competent to incompetent with each antagonist, with the occasional appearance of a serious threat like a Warlord like Kuma or Mihawk and the Three Admirals show up in which the situation drastically becomes more threatening. Then Akainu, the last of those three Admirals makes his debut and completely breaks the Status Quo by killing Ace, and the story's gotten significantly more Darker and Edgier in both in story and its enemies, while still retaining its positive elements.
Kirby: Right Back at Ya! features some Demon Beasts/monsters that take the otherwise lighthearted and comedic anime on a turn for the darker and more dramatic. First up, we have Powered Masher / Masher 2.0 in a Darker and Edgier episode of the same name (in English, of course). Sure, Masher was already powerful enough in his original appearance in the second Knuckle Joe episode before that, but Masher 2.0 is even more dangerous and powerful than he was before. He did a good amount of damage to Knuckle Joe and even now comes equipped with a powerful laser. After Joe defeats Masher 2.0, everything goes back to being comical and happy, until...
...we get introduced to Mumbies in Episode 84. This dude is considered to be even more dangerous than most of the bad guys Kirby's already faced before. Throwing in a creature that Kirby almost can't fight due to its trickery and supply of surprises was enough to give Kirby himself a hard time. And this thing's not the only one; there's even more Mumbies scattered across the universe, hidden on each planet all with the same goal of causing chaos and killing Star Warriors. After Kirby defeated this particular Mumbies, everything went back to happiness and humor. But not for long...
Twelve episodes later came the even Darker and Edgier five-part series finale, which featured the truly competent Destrayers. These things were the main reason why Pupu Village / Cappy Town was getting burned to a crisp and suffering from a Sugar Apocalypse. In fact, a blast fired from one of the Destrayers even knocked off a piece of... you guessed it... Kirby's WARP STAR! Yikes!
City Hunter is a strange version. It started serious (albeith with some dose of silliness), then got comedic in the Sayaka Ryujin arc and stayed comedic for most of its run, only for Sonia Field who wants to kill Ryo because he killed her father, who also was his partner at the time to bring back the seriousness. There had been other serious story arcs (chiefly Rosemary Moon's), and it happens that Sonia's father forced Ryo to kill him to protect her, but this time the story remained serious as it was before Sayaka Ryujin, culminating in the major antagonist of the initial part of the manga returning to settle the score.
Tenchi Muyo GXP has Tarant Shunk, a man so ruthless that even other pirates fear him. The episode that introduces him is the first and only one in the entire series to show any violent bloodshed.
While the original Queen's Blade series (both the anime and the original gamebook continuity) didn't have any of them (except Aldra in the Rurou no Senshi manga), in the QB Rebellion sequel we have three of them for continuity: Captain Liliana and Ymir in the anime, as Liliana stole Vingt from Huit, and later Ymir uses dark powers for controlling the undead, and Sigui in the gamebook continuity, as she's the one of the few people that gives Annelotte, the main heroine from Rebellion, a real challenge.
Comic Books
Cerebus didn't actually have one of these; the major turns for the Darker and Edgier usually (but not always) involve the scary-as-hell matriarchal fascists called Cirinists, but there's no one character that fits the bill.
During the 90s comic book phase of 'grim and gritty', DC's Justice League was played for laughs by Giffen and DeMatteis until the arrival of Despero in JL #38 and his subsequent killing spree (including killing a team member's parents) and introducing a new 'serious' phase in the history of the book... whose readership then tailed off.
And with the advent of Infinite Crisis Justice League ally Max Lord was retconned into being one of these. His recent return as a White Lantern ramps this Up to Eleven.
The supervillain Harm in Young Justice; the first page of his first appearance is marked by Arrowette, bloodily impaled with one of her own arrows, saying "But that's n-not funny..."
Willy Pete in Empowered gruesomely killed a bunch of people by literally raping them to death (which is all too easy for him to do, as he is a fire elemental who cannot shut off the powers that make his body superhot) in his very first appearance. Note that we're talking about a comic book that was almost purely comedic up until this moment.
Since he is a fire elemental, his raping them to death wasn't done in any of the normal ways, because the meat burned away too quickly. So he'd use an eye socket, since the skull would hold the pressure better. More durable sorts he tended to cannibalize (occasionally as they watched), since he couldn't eat normal food because it burned up in the same way; superhero meat would resist longer and be perfectly cooked by the time he could eat it.
Ninjette's pursuers, while having their moments of black humor, ventured firmly into this territory when they hunted her down, and after suffering much pain, decided that the best way to bring her back without further incident was to chop off her arms and legs, which she wouldn't need anyway to fulfill her destiny as a ninja baby-maker. She was saved by her friends in the nick of time, but the mental image of what they tried to do left her a bit unhinged for the whole next volume.
Scott Pilgrim is a Wickety comic, and starts out very happy until Gideon shown up and stabbed and killed Scott and Ramona (well, Ramona almost gets killed).
To a lesser degree, the Katayanagi twins also messed up the comic's quirky nature.
The appearance of the Anti-Monitor in Crisis on Infinite Earths was such an Up to Eleven example (just like everything else about Crisis On Infinite Earths) of this trope that he not only ushered in Cerebus Syndrome for the entire DC multiverse, but induced a CosmicCerebus Retcon upon its entire history. However, instead of taking the danger to a new level, he instead warped the fabric of reality into the Dark Age and all its Darker and Edgier '90s-ness, since no one since has ever been able to come close to either his threat level or evilness level.
Sonic The Comic, while becoming somewhat dark as the issues passed by, really started becoming dark once Super Sonic appeared. It got even worse when he separated from Sonic and even more worse when Chaos appered.
Archie's Sonic the Hedgehog comic similarly started out rather lighthearted, but Robotnik was gradually made more and more into an actually menacing villain, and as he did the general tone of the series grew darker, and the constant gags and attention to construction that fueled the early installments gave way to constant peril and at least one issue that was almost entirely traced. Then Robotnik died and the comic turned to high school relationship drama, and I'll leave it up to you what effect that had on the tone of the series.
Played with upon Robotnik's return and revamp as "Eggman". While he's still the biggest threat in the series for the large part, and has played part in the mass genocide of several notable characters (as well as robotocizing Sally Acorn and seriously wounding Antoine), it is merged with an unusual dark comedic wit and whimsy that matches his other more inneffectual counterparts. He even has his two mooks from the games to banter with as he simultaneously terrorizes Mobian civilians.
Darkhell is believed dead several time, but everytimes he shows up, it always ends up with people dying. Even more extreme, the flashback show that he did a lot of horrible things in the backstory : so far, almost everything bad to ever happen on Alysia has somehow a connection to him... no wonder he became The Dreaded in all Alysia.
While the Guardian was more of a Lawful Neutral type than an actual villain, his role as an antagonist in book 2 caused the whole cast to die, ironically because of him).
While Skroa didn't really have time to cause much harm at his introduction in book 2, his come-back in book 7 and 8 caused a lot of death and almost led to the extermination of the Jaguarians. Spoilers about the next book suggest that he might do ever worst soon.
The Nodwick print comic, in order to move from the gag-a-week strips show in Dragon Magazine into a Myth Arc, introduced one of these as a Big Bad: God of Evil Baphuma'al, who was a lot more competent and Genre Savvy than Dragon villain Count Repugsive (though, really, outdoing a villain whose first 'Evil Plan' was using his undead armies as part of a blockbusting scheme isn't that hard to beat...). Repugsive did get A Day in the Limelight in the print comic (where he ironically came closer to conquering the world than Baphuma'al did), but the plan was mostly Played for Laughs (it involved turning the universe into an 8-bit platforming game) and the heroes defeated him fairly handily. Repugsive inadvertently got mixed into the main storyline and ended up helping to save the day in the end; the villains attempted a Grand Theft Me scheme to upload Utharr's mind into his body, and failed because Repugsive's mind refused to let itself get entirely booted out.
While stories about Batman are normally not comedic or light-hearted in nature, The Joker's reappearance in Death Of The Family, after a year-long absence, certainly changes the mood to more dramatic, more serious, and terrifying! Where Night Of The Owls felt like a mystery/action thriller, Death Of The Family feels like a horror story.
Paperinik New Adventures has Due and High Caste Evronians (or higher). Where most of the series tend to be still comedic in spite of being Darker and Edgier for Disney comics, Due's four appearances are some of the few times where Paperinik nearly gets killed, and the Evronians, usually relatively harmless villains, shows exactly why they are the dominant power in the galaxy and have never suffered a major defeat before when High Caste members show up. Needless to say, those times where both Due and Evronians of the highest caste showed up were among the most dangerous issues of the entire run, with Paperinik only surviving due sheer luck (the first time the Evronians were pissed at Due for hijacking a group of newborn warriors and saved Paperinik by taking them back and waiting until they were recovered before blowing up everything, and the other was only due the Evronian Chronical Backstabbing Disorder getting in the way at the last moment).
Transformers More Than Meets The Eye: Has all sorts of quirky humor and conflicts. The Decepticon Justice Division's appearance turns their arc into a desperate struggle for survival against a team of Knight Templar troops. Their ruthlessness makes all Decepticons current and former dread. Overlord's appearance Transformers Last Stand Of The Wreckers didn't have the light tone to make him contrast as much, but here, he just decides to go out and murder a bunch of people, and goes on a rampage through the ship.
Fan Fic
Dungeon Keeper Ami: a strange, strange example in the form of Mukrezar. Mukrezar is a goofy, slightly manic Keeper of dubious competance. He dosen't even look threatening, he's a pink-haired elf! Following his resurrection he serves as a decidedly plucky comic releif sub-plot and foil to Ami's introverted competence. Yet despite all of this, the story has not only arguably taken a turn for the darker since his introduction, but the level of threat posed by Mukrezar has risen exponentially with his every appearence. Why? Despite dubious success in most of his Zany Scheme -ness, his sadistic streak and ability to bounce back from crushing defeat is intimidateing to the extream.
ChaosGallantmon from the Tamers Forever Series. Before his appearence, the series was a lighthearted romantic comedy series. However ChaosGallantmon's appearance kicks the series Myth Arc into high gear by triggering the series first Wham Episode. And his second appearance is the catalyst for the series Darkest Hour.
For an even more extreme version of this, we have Daemon. See Darkest Hour for more information.
Saint Ayame and Saint Sarutobi from One Piece: Parallel Works. We first see them trying to enslave an entire island, which Aria talks them out of. But, as the series progresses, we learn that they've done some pretty nasty stuff, especailly to Heathcliffe and Yuki-Rin. Kicking Heathcliffe out of his house and killing Molly's parents ( even though her parents faked their deaths) don't even begin to describe how they've also almost brainwashed Holden by sending him to a boarding school for the children of the Tenryuubito. It's also implied that Saint Ayame frequently beat Yuki-Rin for her love of pirates.
Getting Back On Your Hooves had some sad moments in the beginning, but mostly a rather lighthearted story about Trixie trying to do exactly what the title says...Then CheckerMonarch enters the picture. Word Of God states her mannerisms were based off those of a Sociopath if that's any indication. Example? She Mind Raped Rainbow Dash and convinced the Diamond Dogs not to try anything funny with her by saying she'd turn their mine into a parking lot...with them under it. That was only her second appearence.
The Pony POV Series has Loneliness; up till she showed up, the Reharmonization series was much more light hearted than the Discorded Ponies series — it had its dark moments, yes, but nowhere near the amount of Nightmare Fuel Loneliness brought with her. Not only that, but only a couple of chapters later the Princess Gaia arc started up.
Nightmare Eclipse/Paradox manages to be this for Dark World, which was alreadyDarker and Edgier. When the story finally turns to her, it instantly becomes a WhamArc and the stakes go simply from freeing the world from Discord's tyranny, to having to save the entire timeline from being erased from existence due to her Groundhog Day Loop plan. Add in her rather frightening Faux Affably Evil personality and the fact she has the largest body count of any villain in the fic due to having gleefully erased the entire timeline and everyone in it several million times and she's most certainly this trope.
In The Dresden Fillies, the story takes a darker turn when Trixie and the Nightmare kidnap Spike.
In My Little Denarians, the Denarians. Discord may be more powerful, but the Denarians are more evil.
Shards Of Memory, the story takes a much more foreboding turn when Chaos makes his entrance. Killing Cosmos was just the start of the havoc his introduction caused.
Umi Tsuda in Windows of the Soul. The first time she shows up, she tries to kill Shizuru for killing her fiance, and the parts in which she's involved are some of the darker parts of the fic.
Earth And Sky: A mild example, all things considered, but Diamond Tiara's entrance into the story (followed shortly after by the Flim-Flams) not only brought in actual antagonists, but also an overall darker tone to the story.
Subverted with Chrysalis. At first it looked like she was going to be a Knight, but instead was reduced to an Ineffectual Sympathetic Villain, whose one major act of villainy (framing Rarity being a changeling) was negated within hours.
The Powers Of Harmony: While it was fairly obvious from the start that the story was ultimately going to go in a dark direction, it was pretty easy to ignore, given the story's mostly light tone for most of Act 1. Then, just after the Guards' Dark Secret and backstory are revealed at the beginning of Act 2, Cetus shows up, and everything goes straight to Hell.
Star Wars: Paranormalities: While Maesterus is one of Zolph Vaelor's most dreaded foes throughout Episode I (Zolph is defeated by him three times, and he killed his father), he is a charismatic Anti-Villain at best, as he prefers not to kill his enemies. The Forceless Collective and their generals, the Archfiends, are not so kind in comparison. They are perfectly willing to kill and possess other beings without second thought (and for elaboration, the victims are consciously aware of it, and they don't get control of their bodies back unless they serve willingly). While they seem to have ambiguous morals in their debut appearances since they don't talk (usually) and are pretty bizarre to begin with, this gets jossed near the end of Episode I when they are revealed to be capable of sadism and are also willing to resort to psychological warfare.
Film
Something Wild is a quirky comedy - til Ray Liotta makes his entrance.
The Boondock Saints is a series with lots of laughs along with the kickass action. But when Il Duce gets called in, things get serious very quickly.
The original Star Wars Trilogy had one of the darkest villains of all time in Darth Vader but when Emperor Palpatine shows up in Return of the Jedi, suddenly Vader seems like a pretty nice guy.
When Darth Maul first showed up in The Phantom Menace, the movie got darker and it led to the death of a major character.
Rattlesnake Jake from Rango, whose appearance instantly stops the funnier bits of the movie.
Lampshaded when Rango starts to make another joke, but Jake cuts him off by showing his fangs.
The first half of Duck, You Sucker! is a Black Comedy, as we watch bandito Juan Miranda try to convince Bomb Throwing Anarchist Sean Mallory to join his bank robbery attempt, whilst getting into a lot of trouble in the process. Then Colonel Gunther Reza arrives, murders Juan's children, and turns the entire film into a serious drama.
El Indio from For a Few Dollars More is an interesting case. The film has several moments Played for Laughs, but every time when he appears, the film becomes very dark, addressing issues such as psychopathy, drama, cold sociopathy, Kick the Dog moments and that would not be out of place in a thriller.
This Is England started off as a edgy but nice enough movie about a twelve year-old befriending some affable skinheads who protect him from bullies. Then racist thug Combo crashes the party (literally) and the film immediately takes a dark turn.
The Big Bad of Galaxy Quest, Roth'h'ar Sarris, is actually pretty disturbing for a sci-fi comedy movie villain. He even guns down most of the main characters but beheads his second-in-command, and he even has a Nightmare Fuel design.
After Daniel Craig took over as James Bond we had the menacing Le Chiffre in Casino Royale and the cunning Dominic Greene in Quantum Of Solace. But the drama didn't really kick off until Raoul Silva made his entrance in Skyfall (though he's a Large Ham in true Bond tradition and is funny along with being threatening).
The David Trilogy and its eponymous character took the Animorphs series down a darker path than it had ever gone before, forcing its heroes to extreme measures in order to attain victory. While the series was never particularly lighthearted, the trilogy's aftermath saw the War Is Hell aspect really kick into overdrive, culminating in the last ten books.
Nihil from Brian Clevinger's Nuklear Age, who single-handedly transforms the story from a goofy, episodic, villain-of-the-chapter superhero parody into a tragic, post-apocalyptic drama. All of which is intended, by the author's own admission, as one huge joke on the reader.
The Denarians in The Dresden Files are literal Knights of Cereberus, and far scarier than anything that has previously appeared. Things tend to get a lot worse (particularly if you happen to be a Knight of the Cross and all around nice guy).
It's notable that a series as dark as The Dresden Files can even have Knights of Cerebus. After all, previous antagonists were a drug dealing warlock, psychotic werewolves, a ruthless and vindictive vampire, and an insane member of the fae. But none of them were as evil as the Denarians are.
In the Codex Alera books, the Vord are definitely this. While they make an appearance in the first book, their importance grows quickly to the point where they become the Big Bad by the fifth, completely dominating the previous enemies.
While the newly-revealed backstory for the Ring made it obvious that The Lord of the Rings was going to have a darker tone than The Hobbit, this doesn't really hit home for either the reader or the characters until the introduction of the Nazgul, and especially of their true nature.
Especially noteworthy in that their appearance was completely unplanned: at first, Tolkien wrote about a man in a gray cloak on a white horse (namely, Gandalf finally catching up)...then changed both to black, and took the story into whole new not-Hobbit directions.
The introduction of Dolores Umbridge in the following book didn't help - while not the most evil villain in the series, she's easily the most rage-inspiring among fans. As if that weren't enough, the same book also properly introduces Bellatrix Lestrange*
Bellatrix Lestrange had earlier appeared in the Pensieve in The Goblet of Fire after Harry accidentially stumbled upon the Pensieve, although it took place in the past and thus doesn't count
The Yuuzhan Vong indirectly killed off Chewbacca, and Anakin Solo died fighting them. They completely destroyed the New Republic. The Star Wars Expanded Universe took a dark turn the minute they showed up and it has not been able to regain a lot of lightheartedness since.
Atlas from Percy Jackson and the Olympians is the first titan that the heroes fight, replaced the comedic one-shot villains that the heroes defeat during their journey with invincible skeleton warriors that constantly chase down Percy and his friends, and his apperence lead up to Bianca and Zoë getting Killed Off for Real.
While the earlier villains of Septimus Heap were usually too stupid to be real threats most of the time, Tertius Fume since Queste is the first antagonist that became a threat to the Castle itself, signaling the more serious events of the later books.
In Stephen King's It, while it still had bullies, it is this when IT shows up
While opening with a death, Neil Gaiman's Anansi Boys doesn't get truly dark 'til the introduction of Tiger and Graham Coates subsequent possession.
It is said that in the Book of Genesis that God created the Garden of Eden for Adam and Eve to live in. It was gorgeous. They would've lived happily ever after in the Garden had Satan in the form of the Serpent didn't decide to screw them up. After the Fall of Man, The Bible discusses genocides, rapings, and so on.
The Discworld series started out as a rather dark satire or fantasy tropes, but it was still intended as a tongue-in-cheek comedy, with a protagonist who was a wizzard [sic] who only knew one spell and couldn't cast it. Then Terry Pratchett branched out with some other characters who are pretty awesome. Then he discovered Sam Vimes, who took over the book he was introduced in and dragged it, kicking and screaming, into the Century of the Fruit Bat. Since then, Pratchett has had to work quite hard to keep Vimes and his coppers from taking over any Discworld book he writes.
Live Action TV
Power Rangers' Big Bad is always either this or a Large Ham. It's rather rare for them to be both, though. Some examples:
In the original Mighty Morphin' Power Rangers, Lord Zedd fits the trope perfectly. In a series known for ineffectual series of monsters and goofball villains, Lord Zedd almost singlehandedly reversed that in his debut by locking Rita Repulsa back in her trash can, restoring Goldar's wings, and causing the destruction of the rangers' old Dinozords. Though the old pattern eventually reasserted itself, Zedd himself was such a serious villain for the show that his character was eventually watered down to avoid scaring the kiddies.
And when Lord Zedd started losing his edge we got the superficially goofy Master Vile... who had MUCH stronger monsters, which would routinely trash the rangers, and force them into a corner while he came closer than ever to ruling the earth. Even his monsters of the week were far more dangerous than Zedd's, having annoying special powers and almost never being defeated in a lame one hit kill zord battle (Despite the rangers having STRONGER zords at this point). And he's easily the most Genre Savvy villain that Power Rangers has ever had; after many failures at defeating the Rangers, what does he do? He goes back home, where as he puts it, the bad guys always win.
Trakeena from Power Rangers Lost Galaxy actually started out as Daddy's Little Villain and grew into a Knight of Cerebus. Of course, a lot of the events were touched off by Deviot, so maybe he's the real one responsible.
Before Trakeena or Deviot, there was the Magna Defender. Not a villain, strictly, but just as bad at first - the series' first Anti-Hero, he was on a Roaring Rampage of Revenge and willing to sacrifice innocents (albeit reluctantly) to do it.
Divatox is a weird example. In the movie, she was supremely goofy and whiny, played 100% for laughs, and the evil demon-thing Maligore served this role. In the TV series, at least for the first half of the season, she got a new actress and was a bit more serious. Ironically, when the old actress returned and went right back to being ridiculous, she destroyed the Rangers' base and powers successfully, leading to the season's Cerebus Ending. Viva la Diva!
Power Rangers Samurai has Serrator, who appears near the beginning of Super Samurai. Not only is he responsible for making the Deal with the Devil with Dayu that turned her into Nighlock, in the process erasing Deker's memory and turning him into a half Nighlok cursed to walk the earth searching for the ultimate battle (which wasn't part of the deal, Dayu thought she was saving his life!), which he admits to Dayu's face that he enjoyed every minute of, he's leagues beyond the Rangers and routinely beats them down. On top of this, the Nighlok he brings with him are pretty much living torture devices.
Not to mention why he did all these things. He needed Deker the way he eventually became, and the suffering his Nighloks caused as raw material; it's all part of The Long Game to do in one stroke what Xandred and company were trying to do one monster at a time and he nearly succeeded. He didn't do what he did For the Evulz; he's quite a Magnificent Bastard. And even once he was gone, the consequences of what he did to Deker and Dayu only got darker. In the end, since Dayu's grief over Deker's Final Death is what allowed the injured Xandred to restore himself and become immune to the sealing symbol, Xandred going from Orcus on His Throne to the real menace he was in the finale is also courtesy of Serrator.
Power Rangers Dino Thunder had Mesogog. In comparison to just about every other Power Rangers series, nothing about Mesogog was played for laughs, and he never cracks jokes or engages in comedy antics. He also looks pretty damn menacing, and his voice was a perfect complement.
MASH inverts this. Its one-shot villains, usually a Colonel or General, often have a high casualty record or disregard for human life. The recurring 'villains' like Burns or Flagg are comically inept.
Angelus in Buffy the Vampire Slayer. Not that the show was exactly family friendly up to that point, and plenty of the villains had been genuinely dangerous, but from mid season two (when Angelus turned up) onwards, the show got noticeably darker. Some mention has to go to Spike as well, as he was the one who kicked off the storyline.
For the Spin-OffAngel, Daniel Holtz qualifies big time. While Angel was pretty dark anyway, Holtz was a sign that Angel's quest for redemption may be Unwinnable by Design. He manages to put resident Magnificent Bastard firm Wolfram and Hart under serious pressure when he manipulates them, successfully causes a long-term fracture in the team, and despite dying he basically achieves his goal of revenge, in fact his death is all part of his plan, which works and has consequences which last long into the last season.
Dark Willow could also count; between her excuse for her actions, the fact that she shows no reservations about killing (or worse) the main cast despite being their friend originally and almost immediately offs the previous Big Bad in a truly brutal fashion (not that he didn't deserve it), she may also be one of the most efficient villains on the show for such little screentime.
Scorpius, in Farscape. Within a few episodes he tortures the main character, kills his love interest and usurps the previous villain.
Serial killers Mr. Yin and Mr. Yang on Psych. The latter played mind games with Shawn, and later hooked Shawn's mother up to a bomb; and the former murdered Mary, kidnapped Juliet and Abigail, placed them into death traps to taunt Shawn, and got away scot free (for now). A terrified Shawn even remarked during the Yang case that his constant wisecracks were a coping mechanism to keep himself sane.
But since he had to focus all his energies on solving the case, he asked Gus to pick up the slack in the goofiness to keep him from cracking under the stress (with hilarious results and lots of awkward looks from everyone else).
Supernatural: when Mary Winchester showed up in Season 1's "Home", everything started going downhill. The writers even lampshade it in the commentary. After they realized how well Jensen and Jared worked together, they made everything more emotional, darker and less comedic...if you ignore "Yellow Fever", "Hollywood Babylon", "A Very Supernatural Christmas", "Mystery Spot", "Monster Movie", "Fallen Idol", "Changing Channels", "The Curious Case of Dean Winchester", "The Real Ghostbusters", " Sam Interrupted" and "Bad Day at Black Rock".
Ashes to Ashes has two fairly spooky but ultimately ineffective villains in season one's Clown (who is more a mental/emotional villain for Alex than a true threat) and season two's Martin Summers, who doesn't directly hurt anyone. That changes in season three, when Jim Keats is brought in.
It is pretty hard to pin down the exact point when Castle has started to become darker, but the 3XK certainly fits this trope. Especially since his introductory episode was the series' first one to have a real Downer Ending.
Kamen Rider OOO is a goofy series about a homeless man fighting greed, but it soon got crazy when we meet Dr. Maki, learn his backstory, and find out about the purple medallions. Before Maki's appearance, there were legitimate villains, but the episodes were still Strictly Formula, and Maki is soon elevated to Big Bad status.
Also a case of Crouching Moron, Hidden Badass. At first he seemed comedic, with the doll on his arm and messing with it being his Berserk Button, and it would always move while offscreen. While a Mad Scientist, he was under Kougami's thumb, and was the only one who thought his working with The Starscream Kazari was actually a secret. Nobody could have forseen that Creepy Doll Guy was going to turn the tables on everyone and become a dark and deadly villain and shoot past Kazari and Big Bad Wannabe Uva to the top of the heap.
Star Trek: The Next Generation initially gave us the Ferengi, an Ineffectual Sympathetic Villain race that was meant to be the new Big Bad on the level of the Klingons and Romulans from the previous series. This didn't quite work out, due to them being comically short trolls with a lust for money and rampant mysoginy. Then the Borg were introduced, and became the number one ultimate threat to the Federation for the entire series, despite only appearing in six episodes. In their first encounter with the Borg, the Enterprise was utterly defeated and on the verge of being dissected and assimilated before Q rescued themnote After having exposed them to the Borg in the first place in order to give them a kick in their smug complacency..
Q: You judge yourselves against the pitiful adversaries you've encountered so far. The Klingons, the Romulans; they're nothing compared to what's waiting.
Other
Makuta from BIONICLE started out menacing enough, but his constant defeats and failures gradually robbed him of his credibility. After the original head of the Story Team left, the character of Makuta underwent a serious retcon, which resulted in him turning into a calculating mastermind who had planned his victory from the start, turned out to be the Bigger Bad behind a lot of former villains, and by the end of the story arc, ended up winning.
Theater
Camelot is extremely lighthearted up until Mordred arrives, and then starts building toward a genuine tragedy. This could easily have caused Mood Whiplash, but it's handled extremely well.
Also in Into the Woods when the female giant shows up in act II, lets just say things go down hill from there.
The Archmage in Grim Grimoire. The moment he stops being mentioned as being a defeated threat and starts being an active character, things get a lot more serious, fast, and what was once a light-hearted magical school drama becomes much darker.
Hawke in Advance Wars 2 manages to simultaneously pull off a Knight of Cerebus and a Worthy Opponent. While the game's Quirky Miniboss Squad are about as quirky as you can get without major surgery, Hawke is serious to a fault and Dangerously Genre Savvy, especially when facing off against Eagle: when his giant sea fortress comes under attack by Eagle's squadron is approaching, he says "how predictable" and surrounds it with anti-air units, forcing the player to resort to clever tactics and massive casualties. And later on, he decides to stop Eagle from interfering all together by forcing his troops to march past a place where his air units can't go: an active volcano.
Kurtis looked like one of these in the first Disgaea game; up until that point, Laharl's major enemies (Unknown Rival Mid-Boss, Love Freak Flonne, Dirty Coward Madeiras and Lord Error-ProneCaptain Gordon, Defender of Earth!) had been little more than comedic interludes, to which the cyborg proved to be remarkably strait-laced by comparison. It turned out he was neither particularly evil nor particularly competent—the real Knight of Cerebus was his boss, General Carter. Who had, it later turns out, made a deal with Vulcanus (who was being manipulated by Seraph Lamington)!
Kurtis is nothing compared to Judge Nemo in the fourth game, or real Overlord Zenon in the second game in this regard.
Malice in Riviera: The Promised Land. Her first appearance is part of a very dark scenario, but the game returns to its lighthearted self when she leaves. Her return marks the shift of the game to its main themes and the serious core of the series.
The Lego Adaptation Games are a barrel of laughs and fun to play, in Lego Star Wars, the Emperor doesn't abide by this rule, he rarely has any funny scenes to show, minus one with his alter ego, he's more or less played seriously in comparison to the rest of the games. Lego Harry Potter has an odd aversion of this trope with Voldemort, who ends up more like an Ineffectual Sympathetic Villain.
Final Fantasy V brought us Exdeath. While he did become a comedy goldmine in Duodecim and Dissidia, it's worth noting that the game's tone became incredibly serious whenever Exdeath showed up. In a game like Final Fantasy V; which is very lighthearted and at points silly compared to it's predecessors (and many successors), Exdeath's appearance always seemed to stop things flat and ram into the player the severity of their situation.
Final Fantasy VI is a generally light blend of mild angst and whimsical humor...up until Kefka usurps the power of the Warring Triad and causes the apocalypse, creating the World of Ruin and becoming a god. The tone of the game completely changes after, focus shifting to the characters trying to rebuild their ranks and find reasons to continue living in a barren and dying world.
Kefka is also this to the series in general; with the exception of Cloud of Darkness, all prior villains were generic Tin Tyrants who wanted to take over or destroy the world, and aside from being Evil Overlords none of them got much characterization. Kefka on the other hand quite clearly loved the carnage and destruction he was causing and gleefully Kicked The Dog every chance he got just for the hell of doing it. Since him, the villains of the series have become more sinister and ambitious.
Mortal Kombat 9, as per its series tradition, is normally gory, but things do start out looking good for the heroes despite Raiden's attempt to change the timeline. Then Shao Kahn becomes one by killing Kung Lao right after his victory over Kintaro, showing that Raiden's actions started to have disastrous effect. The bad news, that's just the minor one. The next time, Sindel becomes empowered with Shang Tsung's souls... and brutally murders the majority of the good guys, effectively putting Raiden and the Forces of Good at a severe disadvantage.
Bowser himself actually became this in the games Super Mario Galaxy and Super Mario Galaxy 2. Granted he's still humorously hammy as always, but at least he holds onto the fearsome Big Bad role this time.
Mega Man Zero was already the darkest series in the franchise to begin with, but when Dr Weil appeared in the third game, the already dark series got Even DARKER!
Every game in the Ace Attorney series has one of these near the end.
Ace Attorney: Your rival, while competent, was hardly a monster. The game's first two cases featured villains who were both hammy and incompetent, while the third gave us a morally ambiguous but not entirely evil killer, the fourth case brought legendary prosecutor and murderer Manfred Von Karma. With a super-aggressive courtroom demeanor, demonic voice and appearance, and full willingness to cheat to win, it's a rather jarring turn from the previous case, which concerned a murder on the set of a children's TV show.
Trials and Tribulations: An odd case here in Dahlia Hawthorne. The villainess of three of the games five cases, Dahlia is found guilty of murder in the very first one. However, the true depths of her depravity isn't truly revealed until you see what crimes preceded and succeeded that one.
Apollo Justice: Like the above example, KristophGavin is the villain of both the game's first and last case. And like the above, his murder in the first is nothing compared to what he did to Phoenix and the Misham family. For a game whose other two killers are a none-too-smart Bitch in Sheep's Clothing and a goofy-haired rocker, Kristoph's ruthlessness and intelligence is all the more threatening.
Investigations: Super-serious and super-dangerous international criminal syndicate leader QuercusAlba who is responsible for just about all of the game's events. While perhaps not as villainous as the other entries, he still takes the cake for his stubborn, utter refusal to admit to his crimes.
Investigations 2 has BansaiIchiyanagi. Unlike the killers of the game's previous three cases, he has absolutely no redeeming features whatsoever, his Amoral Attorney streak rivals or even surpasses von Karma (he auctions off evidence from past cases, for one) and he manages to drives Edgeworth into a Heroic BSOD so bad he resigns as a prosecutor! And just when you think it can't possibly get any worse, he crosses the Moral Event Horizonright in front of everyone by telling his own son, in the cruelest way possible, that he would never have amounted to anything without his help. It's no wonder that he pretty much causes until-then rival Hakari Mikagami to go: "Screw this, I'm doing a Heel Face Turn."
Shadow the Hedgehog's introduction into the Sonic the Hedgehog franchise took the series down a much darker and grimmer path. Sonic Adventure had a larger share of dark moments than any of the previous games but ultimately contained an upbeat tone. Sonic Adventure 2 (Shadow's debut) is certifiably a point at which the series started experimenting with much heavier themes and Shadow was certainly a catalyst in the series' move in that direction (which continued all the way up to Sonic Unleashed).
And he also gets beaten out by Mephiles the Dark in Sonic The Hedgehog 2006, who was depicted as having no justifications behind his horrific actions other than enjoying destroying things simply because he could, succeeded in murdering one of the heroes, and even successfully shattered the fabric of existence until he was defeated. He doesn't just get killed, he gets completely erased.
Speaking of Shadow, Black Doom from Shadow the Hedgehog is a pretty dark villain as well, having his aliens invade the world and planning to kill all humans ( though he claims to only be trying to save them from a path of selfdestruction). If Shadow chooses to help Black Doom in the Pure Dark path (and the player must view every ending in order to unlock the real ending) Black Doom has Shadow blow up a city with a bomb. Also, in the real ending of the game, Black Doom paralyzes Sonic, Tails, Knuckles, Amy, Rouge, and Eggman and tries to feed them to carnivorous aliens.
Reflux in Rayman 3 could be argued as such, having probably the fewest humorous quirks in the game.
ZODIAC Virgo from RefleX holds this title for turning what would be a rather regular shmup plot completly on it's head.
The Kingdom Hearts series has always been lighthearted even when being grim and morally deep, being a Disney crossover after all. However, the arrival of Master Xehanort in Birth By Sleep made the game the darkest game of the series, depicting Eraqus being beaten down by Terra before Xehanort finishes him off, Master Xehanort possessing Terra's body to become the current Xehanort, Ven being sent into a coma when he destroys his own heart, and Aqua being trapped in the Realm of Darkness. Heck, the Sequel Hook for the game at the end of Kingdom Hearts II serves to show this guy is in a league of his own, showing him freezing Ven solid and raising mountains of earth with a flick of his hand, instantly making him the strongest being the series had seen up to that point.
Even before Darkrai appears, the game begins to gradually get darker once Dusknoir shows up. Ditto for Primal Dialga. Hell, even Drowzee can be seen as an example of this.
In Pokemon Mystery Dungeon Gates To Infinity, things suddenly get a lot darker when Kyurem shows up personally to attack the hero after his followers fail to get rid of them like he had intended.
Ghetsis from Pokemon Black And White. Would you like some horrific child abuse and attempted murder with your cute monster-battling game?
Colosseum and XD represents this for the franchise at large, as not only is the Orre region Darker and Edgier than the rest of the known world, the Cipher syndicate is much nastier than anything that came before them and a damn sight nastier than just about anything that has come since. The Sequel Hook after XD does not help, and neither does the implications that Ghetsis' plot would have left Unova ripe for Cipher to conquer. In any of the other games' WMG sections, bringing Cipher up darkens the discussion in record time.
As proof, the fanfic Ashes to Ashes pits May and Maxie against Cipher - Maxie already has somewhat sympathetic motives in the source work, so naturally compared to Cipher, he's an absolute saint.
Purple Eyes from Pokemon Ranger Guardian Signs fits this trope to a T. Let's see, before we even meet him in person for the first time, he's beaten Rand badly and kidnapped his wife and daughter, ouright attempts murder (which, mind you, has only been attempted by a few Pokémon villains such as a certain Dragon from Shadows of Almia and the likes of the Pokemon Mystery Dungeon villains) ranging from you and your friends, to the entire region, to the entire human population except himself, he mugs the elderly Societea members (who deserved it, but still), laughs after making Mewtwo attack Edward and Rand, laugh once again at the thought of everyone in Oblivia being killed, as mentioned before, after being broken by questing at the Ranger Union, he turns into a Misanthrope Supreme, tries to convince ARCEUS to kill all humans except himself and let him rule under him. After a battle with Arceus, he deems it unsafe for him to be in the mortal plane and whisks him off to his world/dimension, to be judged. He's certainly unique as Pokémon villains go, and is pretty much Pokémon's answer to Kefka. Not to mention how it looks how he might possibly be related to Sabios, the BigBad from the past missions, and that he at least looks like he's 21 or something... And there's no knowing what this guy has done before he became a member of the Pinchers. There's a reason this guy's entry is spoilertastic.
In the Kirby series, Galacta Knight is revealed to be this in Kirby Super Star Ultra. He destroyed entire civilizations, as shown in flashbacks, and, according to Nova, whom Meta Knight made his wish to fight the greatest warrior in the galaxy to, was so dangerous that he was sealed away out of fear that his power was too great.
Chaos Lord Ledgermayne of Adventure Quest Worlds counts as well. Basically, many villains before it, especially some of the previous Chaos Lords, were lighthearted and comical in nature, and even mainly focused on Incredibly Lame Puns, big deal. Then cue the arrival of Ledgermayne, who proves to be almost invincible due to being immune to regular weapons and magics and even being able to control magic itself. And later, Ledgermayne reveals its plan to cut off all magic from Lore - all without caring about the fact that all life on Lore will die if it itself succeeds, which it is, of course, fully aware of.
Vordred, also proves to be this as well. He shows players that he means business by using his signature spell, the Voiduminance Necrot-Morph, to turn other people, especially the very paladins he was trained to fight and destroy (after all, he is a Paladinslayer), into his undead slaves. And that's not all, his armor, which is made up of Too Many Skulls, is immune to light-based magic, and he gets even more powerful thanks to an experiment performed on him by ArcAttack with the help of the hero, plus he's the reason why Part 1 of the Doomwood saga is Darker and Edgier than the previous sagas in the game before it.
Bloodtusk Ravine's story proves to be the darkest out of all the Chaos Lord areas so far, seeing how Xing & Xang's scheme for the ravine is darker than their previous schemes were, and not to mention Krellenos also lands himself in this spot since he worked behind the scenes during the war between the Horcs and the Trolls and even murdered his own brother Antiphuus. Then Khasaanda kills and usurps her own twin brother, planning to use his powers to exact revenge on Drakath for what happened to her brothers themselves.
Sepulchure himself in the games made by Artix Entertainment that he appears in fits this trope perfectly, seeing as how there's less humor when he's around. In contrast with many Harmless Villains working for him, he invokes fear in others and kills off many people, including the ones in the Guardian Tower he crashed his fortress into, as a show of proving that he means business. Of course, his lack of remorse in turning Fluffy into a Dracolich and causing death and destruction doesn't stop him from being an Anti-Villain with standards who loves his daughter Gravelyn so much that he becomes unwilling to kill her despite her being the Champion of Light he sought to destroy, and is trying to bring back his lost love Lynaria.
Henry in No More Heroes. At the game's halfway point of the fifth ranked fight, things have already been getting darker with Travis actually feeling remorse for the last ranked assassin he fought. Then you notice a trail of blood on the street, leading to a long tunnel to the next fight...where someone is constantly just out of your reach. When you actually reach the next fight, Henry jumps out of nowhere and murders Letz Shake with a single slash, and it is hinted that Sylvia knows who that was. It is at this point where No More Heroes goes from dark comedy to constantly unsettling, with the calls for money becoming more demanding and a major supporting character being killed off. The game is quietly telling you and Travis that you have gone down a very dark path, and there's no getting off anymore. There's someone waiting for you at the finish line as well, and you have seen what he can do first hand already.
The Legend of Zelda: Skyward Sword takes a somewhat more balanced approach with the franchise, using dark elements but also lighter moments within the same game, and also lampshading the series' traits, but whenever Ghirahim appears, the game makes a big change in tone, becoming much more serious. His owner, Demise, isn't much better.
The Flood's appearance in Halo: Combat Evolved could count. Granted, it was a pretty serious story to begin with, what with aliens declaring humans heretics and attempting to purge us from the galaxy, but it was a pretty standard sci-fi alien-shooter story, and the enemies weren't too threatening (the Grunts especially were too whacky to take seriously) . Then we get to 343 Guilty Spark and have to deal with those gurgling abomninations that just won't stay dead. Along with the threat of them getting loose and finding earth, the story went from "resist the aliens" to "save the galaxy" pretty quick.
While Soul Nomad & the World Eaters never where really bright and happy to begin with things turn viciously sinister when the Devourlord enters the stage.
Gray Mann in Team Fortress 2. In his very first appearance he murders his brothers Redmond and Blutarch in cold blood and takes control of their companies, plots to take over Mann Co., and dispatches an army of robots for that very task that the formerly RED/BLU-employed mercenaries must band together to repel for the sake of their jobs. Now, this kind of diabolical behavior is par for the course in TF2, but what sets Gray apart is his dead seriousness compared to the other characters and the absolute lack of humor in his actions and schemes, in contrast to the kindofstuff we usually see in the game and its side material. Even the premiere video of Mann vs. Machine is noticeably darker and more solemn in reflection of just how much the new gray team is playing for keeps.
He's not completely serious considering his robots run on piles of money.
Mass Effect is another series that wasn't exactly light and happy from the beginning, but the series takes a dramatic turn for the darker on the planet Virmire. Things get bad from the beginning, but then Commander Shepard meets Sovereign, whose appearance heralds the apocalyptic mood of the rest of the series. Arguably, the Collectors and by extension Harbinger then one-up Sovereign in the opening scene of the second game, destroying the Normandy and killing Shepard. The heroes never even get a chance to fight back before getting utterly defeated.
A rare inversion of this trope in The Walking Dead with Molly. When she joins the group, the game becomes more light-hearted, like an action movie. When she leaves at the end of Episode 4, things rapidly start going to shit as usual for this game, such as Lee getting bitten, Clementine getting kidnapped, the boat getting stolen, and the deaths of two other group members.
Her backstory plays the idea rather straight though. Also seems more like Dude, Not Funny! considering the severity of things that still happen with her around.
As if the Modern Warfare trilogy wasn't dark enough, things get real serious when Vladimir Makarov appears. He's also a Hero Killer.
The moment Ephidel appears in Fire Emblem 7 is the moment where the game's plot, until then mostly light though with some dark episodes here and there, starts shaping up...
The series tend to follow the general "kill some bandits that are anything but threatening and then BOOM the big bad shows up and stuff gets serious", but so far the one guy who managed to turn an entire game from a mostly lighthearted adventure to a dark rollercoaster of death is Manfloy. His actions cause the death of various characters, including Sigurd and most of the 1st Generation playable units, contribute to the subjugation of most of Jugdral to his puppet Arvis' Grannvalian Empire, cause the evil dragon Loptous to posess Arvis' son and start child hunts, and a whole lot of other very unpleasant things for the continent. Not to mention his granddaughter despises him. The amount of crap this guy did to the mostly peaceful land of Jugdral and its happy map tunes is unprecedented and unchallenged in the series.
Star Fox Assault has the aparoids. In Star Fox 64, the main villain was a standard megalomaniac, and so was the villain in Star Fox Adventures (although the former killed Fox's father, and the latter is quite brutal and is described as a tyrant and dictator who controls the planet with fear). The aparoids, however, intend to assimilate all life in the universe. The aparoids destroy most of the Cornerian Fleet, and General Pepper is nearly assimilated by the aparoids, which almost forces Fox to kill him. Not to mention Peppy nearly sacrifices himself so Fox and the others can get to the aparoid queen, and Wolf, Leon, and Panther narrowly avoid death as well.
Let's not forget they invaded Sauria/Dinosaur Planet from the previous game, and killed many dinosaurs there including the ThornTails Fox worked so hard to protect before.
Web Animation
Red vs. Blue introduces, in Reconstruction, several characters who are entirely serious military personnel, including the Director of Project Freelancer (Dr. Leonard Church), Agent Washington (who isn't actually a villain, but nonetheless marks the shift to a mix of silly and serious for the series) and the Meta, who's a creepy, insane blend of several A.I. It's a considerable shift from Omega's "feast on their bodies and crap out their souls" vibe.
Washington double-dips on Knight of Cerebus duty by coming back at the end of the more comedy-oriented series "Recreation" and offing two major characters on the spot.
Church, after witnessing Washington ruthlessly execute fallen enemy South on Delta's advice, summed it up the best: "Dude, you guys are some cold motherfuckers."
Zetto in TV Tome Adventures, a Blood Knight who usually shows up in each season around the time things are getting serious.
Webcomics
Damien from El Goonish Shive is a great example of this trope, to the point where the author killed him just to stave off Cerebus Syndrome. It didn't really work, as the series has since entered Cerebus Syndrome from a different angle.
Abraham was supposed to be even worse, but the whole thing turned out to be one huge misunderstanding on his part, and after everything was explained to him, he surrendered without further fight. He even got to be funny in places, something that did not apply to Damien. Pandora seems primed to do this in-universe, as she seeks to give her son a world where he can make a difference.
Sluggy Freelance kicks its Cerebus Syndrome off with a Mook vampire named Kullan. He fits this trope because his introduction is (a) pretty much the first strip in the series to end on an ominous note rather than a straight-up funny one, and (b) the start of the "Vampires" arc, Sluggy's first more or less serious storyline.
As the strip progressed, the presence of Oasis, K'Z'K or HeretiCorp is a fairly good signal that a given arc is going to be darker than usual.
Dr. Schlock may qualify. Not only is he involved in virtually every other arc's sinister events, but even his first, still-comedic appearance, as a scientist testing cosmetics on Bun-bun (or, well, trying to), sets up numerous events in the series, including the nanomachine plague. It's not clear if that cosmetic lab—which also did nanomachine research—was part of HeretiCorp or not (and, if it was, if it had been all along, or if Abrams decided retroactively that it was).
Played with in 8-Bit Theater with the Four Fiends. The first two, Lich and Kary are played as fairly serious villains, with their presence resulting in major character deaths (and in the case of Black Belt, Killed Off for Real) and some dramatic moments. The later two, Ur and Muffin subvert this trope, with Ur being killed in an Anticlimax while the Muffin Arc is dealt with humourously as usual.
And then we get Black Mage's "Almighty wizard of infinite evil"-form, which, unlike all other "evils" up to that point, actually causes a major Cerebus Syndrome and manages to kill off half of the cast in less than 10 comic strips before squaring off for THE FINAL BATTLE with the awesomest wizard ever. Until Sarda comes in and reveals his plan, that is.
The Wanderer, better known as The Cheese, from It's Walky!. Anyone who can be ominous and badass even when people refer him as "The Cheese" is obviously not someone to trifle with.
Zebra Girl has always kept a somewhat uneasy balance between funny and dramatic, but it tilted firmly into dramatic territory (and ditched some of its sillier, Fourth Wall-breaking gags) with the appearance of Harold DuVase. This is kind of odd, since DuVase appears at first to be a Harry Potter parody. In the end, he turns out to be something much, much worse...
Jeff from RPG World is the greatest example of this. He kills Eikre's family and makes some pretty disturbing scenes giving a whole lot of drama to a webcomic parodying classical RPG cliches.
Sam and Fuzzy takes a turn for the serious which is arguably kicked off by Fridge. Although he starts off as comic relief, his actions in the "Friday Night" arc drag Sam into the Ninja Mafia plotline that has dominated the last four years of the comic.
Last Res0rt was already pretty dark, but by the time we bring Veled around... she's the Big Bad, and she doesn't leave much doubt of it either.
Even if she does have more comedic value than most as she's easily bored (and eager for entertainment), Veled never comes off as harmless — in fact, when she's bored, she's even more dangerous.
Ozimaar from Jayden and Crusader appeared unexpectedly on page 14 after 13 silly comics and created a nonsensical storyline which lasted 'till December '07 when the author cancelled the arc and skipped on ahead in the story, because the Ozimaar Arc was boring him.
Then Computer re-appeared rampaging through the ongoing story lines and twisting them onto her self.
Despite only appearing once so far, the hooded archer from Slightly Damned counts. Devenol even more so.
Given the ever-escalating nature of Homestuck, there are at least three "candidates" throughout the story so far: the meteor at the end of Act 1 (not a character, but the moment where things start to shift from inventory shenanigans to plot), Jack Noir in Act 4 and Lord English, or alternatively his servant Doc Scratch in Hivebent/Act 5.
The Midnight Crew intermission also had one with Snowman. While the Felt were otherwise portrayed as hilariously incompetent gangsters existing only to mess up with their time powers before getting killed by the Midnight Crew, Snowman came in, and spent the rest of her screentime horribly maiming the fan-favourite main characters.
Lord English could count as this. Before his appearance, every major villain had some sort of comedy to them. Bec Noir wanting bones like a dog would, Doc Scratch as serious as he usually is has some humorous lines. Lord English has yet to do anything supposed to be perceived as comedic. In fact, the first thing he does after his introduction is to go and kill the author, who was absolutely terrified when he appeared. He then proceeded to presumably erased many dead characters' souls from existence with a single mouth laser. Although, his younger self is quite a humorous villain.
The only somewhat-serious The Dragon Doctors gets a lot more heavy once the Crax chapter begins. It's a horrible flesh-and-mind-devouring parasite, and it's followed up on with a serial killer who kills people with nightmarish death spirits, a Die Hard scenario in a hospital, and tragic backstory after tragic backstory.
Kiwi Blitz features the villainess Gear,whose presense is currently the only source of grimness and darkness in an otherwise fun and whimsical webcomic.
The chainsaw unicorn from Modest Medusa. It starts a rather bloody fight in what had previously been a lighthearted comic with no action and heralds the start of the Story Arc.
Schlock Mercenary has played with this trope before, but it didn't stick until the introduction of Admiral Emm. ExtremelyDangerously Genre Savvy, the only reason the Toughs weren't immediately compressed into neutronium and fed into an annie plant was because Admiral Emm wanted to let Colonel DeHaans torture and mind-rip them first, just to make sure her clean-up job on Laz'R'Us nanite information was complete and thorough. The Toughs only survived by handing over an expert on immortality treatment and agreeing to let the UNS mindwipe them. The fact that the very next story arc was the darkest story arc by far didn't help anything.
Xanthe from Sinfest brings in the Sisterhood arc after which much of the series' humor has vanished.
After Mechakara was dealt with, things got sillier again with Dr. Linksano as the main villain... only for a second Knight of Cerebus to emerge: Lord Vyce. "All that he sees, he conquers."
The Entity/Missingno.. In general, if there's a Big Bad of a story arc in Atop The Fourth Wall, chances are they aren't a Harmless Villain.
The sequel follows suit with the following Big BadThe Executor, who while not as serious as Malachite, is a lot more dangerous since he plans to wipe out Earth and any world that opposes his rule.
Mechakara also counts for this one, maybe even more so than The Executor. He is the only villain in the entire feature who is never played for laughs and even Zodd and Turrell are terrified of him in the end.Word Of God says that Linkara was very protective of the character, and wouldn't let Doug write anything that would cause Mechakara's threat to be Played for Laughs. They were even originally planning on doing the switch for Suburban Knights, with Mechakara being forced to play along with the antics, but Lewis argued that Mechakara would rip everyone's throats out before participating in a fantasy quest, leading to his role in To Boldly Flee.
Demo Reel was a pretty sad show anyway, but it got sincerely depressing whenever Donnie's mom got mentioned. For good reason too, as she was an aging actress who committed suicide, leaving her only child alone with nobody that gave a shit about him.
Reflets D Acide started out as a Light Hearted Heroic Fantasy parody with no villains beside monsters met by the heroes. Then, we get:
Belial, who on the other hand play this trope straight
Geronimon in Godzilla and His Amazing Friends. While previous enemy monsters weren't exactly lighthearted, he's the first one to be depicted as explicitly out to kill the group and have planned to do so (previous monsters were primarily predators or space monsters the group happened to come in conflict with). Word Of God has stated that Geronimon's goal is to kill Godzilla's friends one by one, then kill Godzilla himself, and that he's done something in the past that Godzilla will never forgive. He also has the dangerous ability to resurrect other monsters. Not only do he and his monster army nearly beat Gomora and Godzilla to death, it takes the entirety of Monster Island's inhabitants to stop them. And on top of that, he manages to brutally kill Gomora, a recurring ally, by stabbing him to death with his feathers and escape before Godzilla can take his revenge.
Western Animation
Both lampshaded and played straight in The Venture Brothers episode "Victor Echo November." When Phantom Limb gets in an argument with Harmless Villain The Monarch, he shows his superiority by calling for the immediate killing of the Venture family, whom the Monarch has ineffectually antagonized for the whole series. When the Guild henchmen prove to be much more dangerous than The Monarch's Mauve Shirts, Dr. Venture asks, "This is different, isn't it, Brock?" Brock replies, "Yeah, we might not win this one."
Although by season 4 Limb has become rather comedic due to insanity.
The Monarch himself has become much more threatening by Season 4. When the person he's after is not Rusty Venture, he can come off as downright scary.
Though he was introduced in the very first episode, Slade from Teen Titans didn't take center stage until the end of the first season, and the previously light and comedic storyline took a much darker turn. Though humor episodes were still very common later on, any time Slade's around things get dead serious very fast. Things get even darker with the introduction of Slade's master, Trigon, though they return to normal after both are defeated. Needless to say, this was a show that tended to dance a jig up and down the Sliding Scale of Seriousness Versus Silliness.
Mozenrath from Aladdin. Prior to his introduction, the recurring villains on the show had been a bunch of cartoonish joke characters like Abizz Mal and Mechanikles. Then, suddenly, we meet this highly competent dark wizard with an army of zombies and a magical glove which is slowly eating his flesh. Only his flying eel sidekick prevents him from being too dark.
Mirage also qualifies as well, while most of the villains Aladdin and his friends faced are typical cartoon-y bad guys. Her introduction begins by lighting a village on fire.
Nox from Wakfu. When most of the villains of the series are harmless, being slightly ridiculous or just not evil at all, Nox is one hell of a dramatic villain. He is eager to destroy any living things to get their primordial energy, including a baby that he stalked for ten years. And some flashbacks seems to indicate that he's responsible for the death of his own family, and ready to kill anyone/anything to bring them back to life. Altougth it might be a slight subversion, because he was introduced in the very first episode; the later villains were more light-hearted.
Apocalypse from X-Men: Evolution. After he appeared, the series got less goofy and more serious, with more dramatic tension and more focus on stories about mutant persecution, less on high school drama. Apocalypse's ultimate genocidal plan really emphasized this.
Though to be honest, the plot had already become divorced from the High School Drama even before Apocalypse arrived thanks to the triple disaster from Magneto, Mystique, and Trask. All at same time. Mutants become a hunted by the entire world, the School blows up, and Professor X turned out to be an Imposter and the real one is missing. That was not a very good day.
Actually, two other characters predated all of them. One was Wanda Maximoff aka the Scarlet Witch, the other was Mesmero.
King Hiss in the 2002 He-Man and the Masters of the Universe cartoon. Shortly after being released, he defeats Skeletor and his entire army of evil warriors, before breaking into Castle Grayskull. Although temporarily defeated, he later returns and destroys the royal palace of Eternia.
Megatron of Transformers Animated is another semi-example like Slade and Rubilax... Once he gets his body back, things get bad.
Here's one for the Transformers franchise as a whole: Anytime Unicron shows up, things are going to get serious very quickly. This is especially noticable in his very first appearence, which opens up with him destroying an entire planet full of life. He only get's worse from there on out.
Chase Young of Xiaolin Showdown was introduced as the Big Bad in the second season. In the first season, the villain had been Jack Spicer who is comically beaten once an episode. While he was partly taking orders from Wuya (an evil spirit with no physical form), she was also strictly comical, except in the Season One finale. Chase, however, was a strictly non-comical and threatening villain.
Wuya deserves special mention. Like Rubilax, her snarking makes her strictly comedic for the most part... then she gets free and suddenly thelaughingstopped.
In GI Joe Resolute, Cobra Commander himself has become a darker, edgier, EFFECTIVE villain, explaining away his old incompetence as a (failed) method to coerce his minions into being better soldiers (adaptability, resourcefulness, so on). This CC manages to be a credible threat to the world.
In The Grim Adventures Of Billy And Mandys Halloween Special, there is Jack O' Lanturn. While quite comedic, he is shown to be the only villain to outsmart Mandy by not falling for her trap and capturing her. He is only defeated when Irwin, in the most hillarious use of Deus ex Machina shows up and humiliates himself enough to destroy Jack's army.
The Freak of Crystal Cove AKA Mayor Jones is even worse then Pericles. His deeds involve: Chasing off the original Mystery inc. Kidnapping the son of two of their members as insurance to raise as his own, scarring Pericles and pinning Mystery Inc's dissapearance on him, and causing the dissolving of the present Mystery Inc. as Fred leaves to find his real parents, Daphne blames it on Velma for not figuring it out sooner, Shaggy gets shipped off to military school and Scooby gets sent to a farm. And all this from a villain on a Scooby Doo show.
The finale gives us a final one, though only for its two-part sequence: the Nibiru Entity a being whose evil has projected onto everyone, and is responsible for all the costumes, all the cruelty, and all the evil, including that of the previous two. Once freed, he kills Pericles, eats the original Mystery Incorporated, and eats all of Crystal Cove. His destruction raises this to a meta-level — as he was erased from the timeline, all the evil characters grew up to be good, and everyone's lives are for the better, bar Daphne's sisters.
The Lich of Adventure Time is this, as he manages to kill and possess Princess Bubblegum, and even after his defeat, he still manages to live on through a certain background character, though whether or not he'll actually return remains to be seen in the coming season. Nevertheless, The Lich is not immune to slapstick comedy and being made a fool of, although he still has absolutely No Sense of Humor and its also worth noting that in the pitch of the show, it specifically mentions in bold dripping letters that "The Lich King is not funny."
After his return in the season 4 finale, he's still as frightening as ever. He appears in Finn's dream complete with a jump scare, is in possession of the Enchiridion, currently possessing Billy, a famous hero of Ooo and then manages to trick Finn into giving what he wants. Even after being out of the spotlight for nearly two whole seasons, he still shows how Dangerously Genre Savvy he is through manipulation of events without even a hint of humour or sarcasm.
He didn't just possess Billy. He killed him and took his skin.
Even the Ice King goes between Sitcom Arch-Nemesis to saddeningly realistic depiction of dementia.
Granny from the episode "Have You Seen This Snail?". She, unlike other recurring villains in the series (including Mr. Krabs, who is considered funny in his actions even more deplorable), she contrasts absolutely comical traits, and the episode itself made things very serious. Later, she revels who killed all the snails to eat them!
Believe it or not, Plankton manages to be one in The Movie.
In that same vein, the Forever Knights in Ben 10 Ultimate Alien, combined with Took a Level in Badass. In the earlier series and several earlier episodes, they were pathetic mooks that got beaten easily and usually made Monty Python references. In the episode "the Purge" their founder, Old George returns, ends their Enemy Civil War and unites them as one faction to rid the world of aliens, and the excrement hits the cooling device.
While the fourth series Ben 10 Omniverse is Lighter and Softer than the two sequels; Khyber the Huntsman is not played for laughs at all. In fact, he's the first villain in Omniverse to fully defeat and capture Ben.
Malware, a villain who first appeared in the first episode and whose origins were explained in "Trouble Helix", also appears to be heading this way, due to his origin episode, while showcasing his Fatal Flaw (a particularly bad case of boasting and talking on and on), also shows that he has committed murder (though not on-screen; the flashback cuts off before it shows the gruesome details), though the rest of the episode showcases him as what just seems to be another villain, until "Of Predators and Prey" reveals that he's the Big Bad, and shows that him, Khyber, and Dr. Psychobos forcefully test the Nemetrix on Phil, with no amount of comedy appearing.
Hell, when Ben sees him again in "Malefactor", his reaction is to back away in fear. And considering how many life-threatening things Ben's been through without flinching, that really says something about Malware.
And then Malware not only kills some more members of his own species, he tops it off by blows up his own homeplanet.
Toy Story 3 has Lotso Huggin' Bear, who is anything but what his name implies.
Lord Shen from Kung Fu Panda 2. While the first film featured slapstick kung fu fighting and Bloodless Carnage, the sequel opens with Shen ordering a mass genocide, and then a few scenes later he rolls out what he's been inventing during the Time Skip — the cannon.
Him of The Powerpuff Girls, compared to the rest of the show's Ineffectual Sympathetic Villain cast, had a much creepier presence (even noted frequently by the cast and the narrator) and frequently supplied Mind Rape or other much deadlier tactics of bringing the girls to an end. Granted he also often supplied in Nightmare Retardant and did have the occasional bumbling role (he was Camp Gay after all) but he was still miles deadlier than most of the Rogues Gallery. And then there's the episode "SpeedDemon".
Mojo Jojo himself is this in The Movie, where he had a much more dark presence than any episode of the series. He deceives the Powerpuff Girls, and is probably responsible for a mass murder and mass destruction in the city at the climax.
Abrakadaver from the episode of the same name as well.
The Gnome from the episode "See Me, Feel Me, Gnomey". While not as terrible as those mentioned above, is probably the most powerful villain that has appeared in the series, since it seems to be a greedy, Manipulative Bastard that he just wants to be the only villain, a massive hypocrite manipulating and controlling the masses. He is also responsible for killing all the recurring villains of the series.
Played with in The Dreamstone with Zordrak. While he appears in each episode dishing comical banter to his far lessthreatening minions, the Urpneys, he is a genuinely intimidating villain, and the odd time he has an active role in a plan it is usually a sign things are going to get a bit more serious.
Inverted in My Little Pony: Earlier villains (like Tirek) were rather terrifying, while later ones are extremely goofy and hilarious.
The CanterlotWedding introduces us to the Changeling Queen, Chrysalis, who plans to feed off of the love and magic of Princess Cadence's groom, Shining Armor, in order to enable her invading army to breach the magical Deflector Shield that Shining Armor cast over the capital city and seize control over all of Equestria.
She gets even darker in the comic where she turns the Mane 6 against one another (although they get back together and she intended them to), and intends to kill Twilight after draining her magic, and have her changelings feast on her friends when their emotions peak. Not to mention she kills a luvcat in front of the Cutie Mark Crusaders ( whom she also intends to do away with).
King Sombra, the villain of the third season's premiere "The Crystal Empire," is arguably the most evil antagonist yet seen on the show between the sheer scale of his atrocities and the fact that a selfish lust for power is apparently his only motivation for it all.note As mentioned, Nightmare Moon has a highly sympathetic backstory, while Discord and Chrysalis's crimes at least were, in part, a result of their very natures. Unlike earlier villains of his tier, his episode almost treats him less like a character than a disembodied force of hostility (hence his few lines of dialogue; he prefers monstrous roars instead), and in a first for this show, he is seemingly Killed Off for Real in the end. Naturally, outside of some tension-lightening comedic moments, the overall events of the episode are presented quite seriously even when compared to past two-parters.
Babs Seed, while not as dark as the other examples from the show is a much more realistic and scary portrayal of a bully than one would probably expect from the show including her excuse for her actions, especially jarring compared to the relatively harmless Diamond Tiara and Silver Spoon.
In The Lion King, Scar himself qualifies. The film begins quite cheerful, but when Scar kills his own brother and takes the power, the film definitely becomes quite dark. He may be this to the whole franchise as he's the first Disney villain to successfully kill a main character.
Zira is no slouch either. Her appearances in the film are quite dark and her Villain Song is even more intense than the last.
Amon from the Sequel Series, The Legend of Korraalsofitsthis. The couple of episodes before his first appearance were quite lighthearted. Once he showed up, the series has gotten darker and darker with each episode.
The most notable thing about Amon is that he is the only major villain in either of the two series who is never once Played for Laughs or the butt of jokes from other characters.
Even though he appeared in only one movie, Dark Danny, Danny Phantom's Bad Future version, made quite an impression as the most dangerous and psychotic villain in the entire series, even worse than Vlad Plasmius.
Vlad himself served this role in the first season, though to nowhere near as great an extent. His first appearance marked the beginning of the show's main Story Arc, and subsequent episodes that featured him tended to be darker in tone. He was also the first villain to utterly curb-stomp Danny.
Darkseid and the armies of Apokolips in Superman The Animated Series. While Superman wasn't a goofy show, being largely a good combination of silliness and seriousness, the eight episodes where Darkseid appears are much more serious that regular episodes. In "Apokolips... Now!! Part 2", Darkseid kills Dan Turpin, a major supporting character; and in "Legacy Parts 1 and 2", Superman is brainwashed by Darkseid to attack Earth and many other planets, killing who knows how many people. It culminates with a brutal brawl between Superman and Darkseid.
Justice League Unlimited had several end of season threats amping up how much darker things were. The last season had this from the beginning via Gorilla Grodd (himself a recurring Knight). What would top this? At the end of that season Darkseid returns and sets out for revenge against the Earth. Not only does he set crust digging machines all over the world to cover the entire surface in boiling magma, he also brings a kryptonite knife to carve out Superman's heart as a war trophy.
Likewise, Amanda Waller, starting in Season 3 but becomes much more pronounced in Series 4. She masterminded the Cadmus Arc and the episodes dealing with Cadmus and their experiments were among the darkest of the entire show.
Although The Brave Little Toasteris a dark film, it starts getting much darker once the infamous Monster Clown makes his appearance. Alternatively, Elmo St. Peters could be considered a Knight of Cerebus as well.
Yosemite Sam of Looney Tunes is another "comparison only" case. At his best he was an Ineffectual Sympathetic VillainPlayed for Laughs, however he was specifically created to be a far more malicious and active villain for Bugs Bunny than the rather pitiful Elmer Fudd. As Sam eventually became even more harmless than Elmer, Chuck Jones created Marvin the Martian, an Affably Evil alien set on denoting the Earth with an "Earth-Shattering Kaboom". Even Bugs was pretty creeped out by this.
Perhaps the series' oddest move was evolving Daffy Duck into one for Speedy Gonzales. Similar to the above examples, Daffy was still rather bumbling and comical, however he was often portrayed as Speedy's most competent foe compared to the rest of his completely ineffective Rogues Gallery, often putting Speedy and his friends in much more dire circumstances (eg. enslaving them or depriving them of water) and downplaying the former's Comically Invincible Hero streak.
Jeff Fecalman in Family Guy. There is absolutely nothing funny about him in the episode he appears in.
The moment Rattlesnake Jake first appears in Rango, things get really dark.
Also happens in The Movie, with the twist that the Knight of Cerberus in the movie is actually an alternate universe version of the shows regular Harmless Villain Dr. Doofenschmirtz. He is far more competent and scarier than the regular Dr. Doof, has actually conquered his dimensions Tristate Area and is now a cruel dictator who uses an army of robots to keep the population under control, turned Perry the Platypus into his loyal cyborg henchman, and is not afraid to try to kill the protagonists.
In The Penguins Of Madagascar, Dr. Blowhole can be established as one since he tried to melt the ice in the world and flood it so that the humans would have to go through a ring of fire, and in his second appearance, he intentionally tried to drown Skipper when he gave him amnesia.
Miss Power from Word Girl. Magnitudes more powerful than every other villain and WordGirl herself, and much more intelligent. Pretends to be a hero and trains WordGirl while slowly corrupting her and the citizens. When WordGirl finds out she's being played, Miss Power simply beats her up and takes over anyway. And given the nature of her powers, she's pretty much the embodiment of bullying.
Lord Dregg of the 1987 Teenage Mutant Ninja Turtles cartoon. The fact that he plays his actions more seriously than Krang, the Shredder and his goons, who were all Laughably EvilHarmless Villains, definitely shows that this guy means business.
Speaking of the Shredder, he was made crueler and more brutal and competent in the 2003 cartoon. This was just a small change compared to his even more completely monstrous self in Turtles Forever.
While Fast Forward was intended to be Lighter and Softer, Sh'Okanabo, the Big Bad of that season, downplayed the humor in almost every episode he was in.
So far the Shredder in the 2012 series is shaping up to be this. When the Turtles actually face off against him for the first time, they end up getting their shells handed to them; they only manage to escape because the Shredder was distracted by Xever and Bradford mutating.
While the villain of the first Cars film is an arrogant and obnoxious green racecar, the sequel's villains are an organization of evil, beaten-up cars led by a German microcar and a malfunctioning British SUV.
Sideshow Bob from The Simpsons. While still rather slapstick prone and displaying humorous wit (being voiced by Kelsey Grammer and all) most of his appearences he attempts to kill' Bart ( 10-year old boy'') or Krusty The Clown and his intents are (mostly) played seriously with episodes becoming more intense and dark when he appears.
Mr. Burns also qualifies, at least in seasons 1-8. While he does have some comical traits and funny quirks, the episodes with him are more serious and dramatic than any other episodes and his actions are played seriously. Most notable examples are "Who Shot Mr. Burns?" two-parter, where he screws over all other characters and finally blocks all the sunlight from Springfield and this was so evil that his loyal doormat Mr. Smithers objects to this and all of his actions are played seriously and episode is dramatic and intense, not to mention that it is the onlytwo-parter episode in the series; "The Curse Of Flying Hellfish" where he crosses Moral Event Horizon by attempting to drown Bart and in "Mother Simpson" where he worked on biological warfare and made Mona Simpson, Homer's mother, run from the law and hide from the rest of her life, meaning that Mr. Burns is responsible for Homer losing his mother and setting some of the series plots in motion.
The series had few villains who have no funny quirks and are played seriously. Examples include the winemakers from "The Crepes Of Wrath", who treated Bart like a slave and nearly killed him by giving him antfreeze-laced wine, the Babysitter Bandit from "Some Enchanted Evening" (who tied up the kids and tried to rob the house) and Bart's kindergarten teacher from "Lisa's Sax" (whose treatment of Bart made him considered suicide, when he was just a five year old boy and made Bart what he is today).
Frank Grimes is an interesting case. Although he is not a completely vile (only a jerkass), the things turn very dark in his only episode where he appears, "Homer's Enemy". For many fans, is one of the darkest episodes of the simpsons.
Wallace and Gromit: Piella. She murders twelve bakers, and plans on making Wallace her thirteenth. This was because she hated bakers.
While the show on a whole is lighter than previous continuities, Ultimate Spider-Man's version of Venom is, half the time, not played for laughs and there are less Imagine Spots whenever he manages to make an appearance. Similarly, his creator, Doctor Octopus, while hardly ever seen outside of his lab, also appears to have no humorous quirks and if he's in an episode, the episode has a likeliness of taking itself seriously.
And when Norman Osborn becomes the Green Goblin, things really get dark.
Courage the Cowardly Dog gives us Mad Dog. He abuses Bunny to the point where he buries her up to her neck in dirt when she tried to escape, he tried to drive her and Courage down with his car, and most importantly, he somehow caused Kitty to be convinced that all dogs were evil. And that, like Katz, he's played dead seriously, and that he almost resembles a real life abuser.
Katz himself should not be overlooked as well. Whereas the general series dealt with courage battling monsters and whatnot, at least they had some light-hearted tones in those episodes. Katz starkly contrasts these themes as he's essentially Ax CrazySerial Killer played completely, horrifyingly, and competently straight. Courage usually struggles in the episodes he's in, nearly getting killed twice.
Freaky Fred's episode, while still quite funny is a lot creepier than the average Courage episode. And that's saying something!
Legion Of Super Heroes had a very quirky and upbeat first season. Season 2 opened with Imperiex making it to the past to conquer it, setting up the Darker and Edgier season.
The second season of Hero 108 gives us Twin Masters, an Omnicidal Maniac and embodiment of Chaotic Evil determined to destroy all life in Hidden Kingdom. Their introduction take the show from lighthearted to a more serious action show.
Taurus Bulba from Darkwing Duck. While the other villains are comical and overly arrogant, Taurus Bulba is a crime boss of the Magnificent Bastard category who rarely acts comical or over-the-top. Not only did he kill Gosalyn's grandfather, but he also tried to kill her onscreen, just to blackmail Darkwing Duck for a passcode. And it wasn't anykind of Bond Villain Stupidity attempted murder with a slow-moving trap or anything, no, he straight out dropped her from the sky. The best part is that he's the very first villain to ever appear in the show. Then there's Darkwarrior Duck, who's an alternative futuristic version of Darkwing Duck who has gone insane and overzealous on crime, and appearently even killed Negaduck at some time just to prove to everyone who was in charge.
Trent Boyett from South Park belongs to this trope, he played himself seriously all the time in the episode "Pre-School".
The Super Adventure Club from the episode "The Return of Chef", who brainwash Chef and turn him into a pedophile, among other things. The episode on whole is darker (and more bitter) than most South Park episodes.
Grandma Stoch, despite the absurdity of a grandmother acting like a schoolyard bully, is still rather disturbing, especially when she buries a fork Butters.
Sheila Broflovski in the The Movie is one of the few antagonists of the series that has been played seriously in a very short period.
He can be Played for Laughs all the time, but Cartman is played much more seriously in the "Coon & Friends" trilogy.
The Crazy Old Farmer from the episode "Cow Tipping". While probably played for laughs, the series definitely takes a much darker tone by the normal standards.
Daria's Tom Sloane is an interesting example. While not a villain (which this show doesn't have much of, and in fact, he's not an obnoxious guy), he could very well be responsible (whether directly or indirectly) for driving the series into a more realistic and character-building show.
But still, Tom is nothing compared with Jake's father ("Mad Dog" Morgendorffer). Although he never made an appearance in the series (is confirmed to have died), he is probably the worst of all jerks in the series, starting because he mistreated bad his son, did not care what happened to and he did not accept it as he should. Agree to this, a type of villain is very unusual in a series with few elements of violence or domestic abuse like this.
In fact, his own nickname, could claim that he was an extremely impulsive and violent person.
Eddy's Brother from Ed Edd N Eddys Big Picture Show. Consider that he is the only villain in the entire series who has dedicated all his life to physically assaulting children, starting with his own brother Eddy. His abuse on Eddy is still displayed in a cartoony manner but it the trauma is played in a poignant light and is probably the single most serious scene in the entire series.
King of the Hill has Leanne Platter. The whole reason Luanne lives with her aunt and uncle is because her mom stabbed her dad with a fork. Only appeared on screen in one episode where she gets released from prison, but it's clear she hasn't changed a bit.
Trip Larson from Pigmalion. Not only does he try and transform Luanne into his ideal woman, he literally attempts to kill her with a pork processing machine.
In Captain Planet And The Planeteers, the episodes with Verminous Skumm as the primary villain tend to be Darker and Edgier than the rest of the series. He's one of the only villains who specifically wants to hurt and kill people, not the environment.
Futurama has Donbot as this. Unlike other villains, he's played seriously many times.
Subverted as Joey Mousepad and Clamps (his henchmen) are purely comic relief.
, It's Walky!
