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The best '90s animated villains of all time

The '90s were a renaissance when it came to animation. Following a decade of what amounted to toy commercials, TV-borne cartoons finally spread their wings, demonstrating a creativity that had been missing in the '80s and branching out into previously unexplored genres. This included, for the first time in a long time, animated television successfully aimed at adults. Meanwhile, animation at the movies exploded, with Disney building on the success of 1989's The Little Mermaid to unleash a torrent of cartoon classics, as well as introducing audiences to a little studio named Pixar.

Coincidentally, the '90s were also a time when villainy became cool in pop culture. Perhaps spurred by Jack Nicholson's flashy performance as the Joker in 1989's Batman, more and more A-list talent decided to take a trip to the dark side, with actors like Anthony Hopkins, Tim Curry, and Sharon Stone offering up some of the most iconic performances of their career as antagonists audiences loved to hate.

So what happens when you mix golden ages for both animation and villainy? You end up with a rogues' gallery of amazing animated baddies that stand toe-to-toe with the most memorable embodiments of evil ever seen on screen. Here are the best of the worst when it comes to '90s animated villains. They're bad, and they're drawn that way.

Gaston was Disney's greatest animated villain of the '90s

Before "toxic masculinity" entered the popular lexicon, Disney's animated tale of a girl and her monstrous love delivered the absolute embodiment of the term. Arrogant, boorish, uncultured, greedy, and short-tempered, Gaston still manages to be hailed as a hero in Belle's unnamed French village thanks to his prowess as a hunter, his traditional good looks, and a way with cunning that sees him come out on top. Given his narcissism, he, of course, imagines Belle will have no choice but to accept his advances, but the joke's on him when she falls for her beastly captor ... as does Gaston, in a manner of speaking, plummeting to his death in a duel with the monster.

Gaston often gets short shrift in the discussion of '90s Disney movie villains, usually ranking behind the likes of The Lion King's Scar. While the fratricidal feline has his merits, it's Gaston's familiarity that most breeds our contempt. Let's face it. A lot of us know someone like Gaston, who manages to bully his way to prominence despite a rotten core. In fact, script writer Linda Woolverton has stated that she based bits of the character on her own ex-boyfriends.

Megabyte went viral before going viral was cool

When ReBoot premiered in September 1994, there wasn't a ton to Megabyte as a villain. More often played for laughs than for any sort of real thrill, his plots to overthrow Mainframe were thwarted easily by Bob and the Guardians. As the CGI show evolved, however, so did its antagonist, developing into an adversary that combined intelligence, imposing physicality (dig those Wolverine-like claws), and, unlike many cartoon villains, a strategic patience that often led to him having the upper hand against the heroes he battled in his efforts to infect the computer system they all called home.

Notable for his complexity, Megabyte wasn't content to be your run-of-the-mill cartoon villain. His complicated relationship with his sister, Hexadecimal, and his apparent possession of even a small degree of honor gave him a multidimensionality not often seen in children's programming. He was also unique among animated bad guys in that he knew how to win, even managing to banish Bob through a web portal and conquering Mainframe during the Web Wars. While he was eventually overthrown, he returned as a Trojan Horse virus, once again doing all kinds of damage before his plans could be undone. Naturally, he returned to his evil ways when the ReBoot universe was relaunched in Netflix's 2018 series ReBoot: The Guardian Code.

Chairface Chippendale was the best of the Tick's wicked weirdos

While it contained its share of superhero action, The Tick functioned best as a satirical take on the genre, showing us the silly side of the tropes leaned on by so many other shows. Nowhere was this better embodied than in the form of Chairface Chippendale, a James Bond-style evil genius who had the distinguishing characteristic of having a chair in place of a head. Weird? Absolutely. Was it any weirder, though, than the likes of Flyface or Flattop, two of the numerous physically distinctive bad guys from the Dick Tracy universe? Okay, yes, it was. That's The Tick for you.

A carryover from the comics, Chairface was a nattily dressed, well-cultured crime lord. With a gang of henchmen, including his own personal scientist, Professor Chromedome, he was regarded as one of the most dangerous villains in the City, and he proved that a fair evaluation with his first massive scheme: to carve his name on the moon. His plan was, of course, foiled through the efforts of the Tick, but not before he'd actually managed to partially accomplish it, leaving Earth's neighbor with a massive "CHA" on its face for the duration of the series. Diabolical!

Shredder was a villain who could really get under your shell

Okay, so, there have been scarier versions of Shredder than the one who showed up in the Teenage Mutant Ninja Turtles animated series from the '90s. The one in the comics racked up an impressive body count, and the one from the 2012 cartoon was pretty terrifying. There's no doubt, however, that the Heroes in a Half Shell's animated series was a '90s phenomenon, and their greatest foe remained front and center throughout the proceedings. As has been the case in most incarnations, it was his connection to Hamato Yoshi, who would become Splinter, and his position as the head of the nefarious Foot Clan that put him square in the Turtles' sights. And while other enemies would arise, he would remain their primary foe for the entire run of the show.

Despite the fact that his efforts always seemed to fail, Shredder was portrayed as possessed of a keen intelligence, with an IQ of 300. He was also a formidable martial arts master, surpassing the titular turtles and matched only by Master Splinter himself. His greatest problem appeared to be his dependence on undependable henchmen like Rocksteady, Bebop, and his army of Foot soldiers, who rivaled Star Wars' Imperial Stormtroopers for their general incompetence. Although he never managed to come out on top and ended up trapped in Dimension X, it's fair to say that Shredder holds a special place in the memory of TMNT fans.

Megatron was the very model of an ancient evil Predacon

You have to work pretty hard to make Transformers fans associate the name "Megatron" with anything other than the Golden Age version brought to life by the great Frank Welker. It's a testament to the work done by David Kaye in this seminal reboot of the robots-in-disguise series, then, that for the generation that came up in the '90s, his is the voice they most remember. It's for good reason, too, as the Beast Wars' Predacon general is a calculating, cold-blooded foe for the Maximals and Optimus Primal. Though the series' computer-generated animation looks prehistoric by modern standards, it has personality to spare, and nowhere more so than in the form of this T-Rex-transforming villain

Partial to quoting Shakespeare and possessed of a murderous wit, this Megatron, like his predecessor, is eminently quotable, having done more for the word "yes" than anyone other than wrestler Daniel Bryan. He also shares with his namesake a healthy dose of hubris and a lack of patience with the incompetence of his lackeys. He manages to separate himself from '80s Megatron in one key area, though. He's actually effective, winning his war and managing to conquer all of Cybertron so hardcore that it takes Optimus Primal making the ultimate sacrifice to undo it. Even then, Beast Wars Megatron bounces back, reincarnating to battle his heroic enemies again when Unicron kicked off the Universe War in comics form. It just goes to show that you can't keep a bad 'bot down.

The Brain tried to take over the world throughout the '90s

Sometimes, the greatest villainy comes in the smallest packages. Exhibit A in this phenomenon is the Brain, a megalomaniacal mouse who, from his cage at ACME Labs, plots to take over the world. Every. Night. Though his physical stature isn't much to speak of, he makes up for it with a heaping skull-full of mental capacity, concocting elaborate schemes such as dosing the population with a psychoactive toad toxin, publishing a romance novel containing hypnotic text, and developing a conspiracy theory to convince the public that hidden forces are using their unseen influence to keep him from seizing power. Each plan is more diabolical than the last, but unfortunately, they also tend to be foiled by Brain's soft spot for his bumbling friend, Pinky.

Pinky and the Brain's adventures started out as a segment on the now-classic Animaniacs, but they proved so popular that the two were eventually spun off to their own show. Voiced by Maurice LaMarche, the Brain was modeled after Orson Welles, with a little bit of Vincent Price thrown in for good measure. His plans were more often played for laughs than for any real sense of threat, but his intentions were good — um, bad — and for the sheer scope and endurance of his megalomania alone, he deserves a place on this list.

HIM scared the bejeezus out of the Powerpuff Girls and their viewers

Mojo Jojo might get more press, but when it comes to memorable Powerpuff Girls villains, none seared their way into the brain like HIM. We're not sure whether it was the demonic look, the weirdly lilting voice, or the reality warping powers, but whatever it was, HIM had it in spades. His effeminate demeanor and falsetto tones created a disturbing dichotomy with his appearance, which approximated that of a traditional devil but with makeup and outfits to die for. Unlike other villains on the show, he also seemed to revel in sadism for sadism's sake, attacking the Powerpuff Girls not for money or power, but just because he really enjoyed causing them pain. What a jerk.

HIM's modus operandi tended toward psychological torture, as he'd use his powers of mind control and illusion to twist his victims' worlds around. Nowhere better was this demonstrated than in his very first appearance, when he possessed Bubbles' stuffed octopus, Octi, to turn the team against itself in what is genuinely one of the scariest episodes of kids' TV ever aired. It wasn't all fun and mind games, though, as HIM was also powerful enough to telekinetically push the sun away from the Earth. He's so evil, in fact, that to even say his real name is too much for the show's narrator to bear, and we all know one's name not being utterable is the highest badge of honor a villain can hope to attain.

Sid Phillips, Toy Story's psychopathic toy surgeon

Okay, so who among us who grew up in the action figure era hasn't conducted a little transplant here or there, swapping out one character's arm for another's leg, etc.? That seemingly innocent childhood pastime takes on a different shade, however, when the toys are alive, unless you're as sadistic as Andy's neighbor, Sid, the villain of Pixar's debut film, Toy Story. Unlike Woody's owner, who lavishes love and attention on his playthings, Sid is every toy's nightmare, delighting in whatever cruel torments he can concoct and not caring how many disturbing hybrids he has to create in order to get his jollies. That spider-baby-thing still gives us nightmares.

When Sid meets the movie's main toy protagonists, however, his villainy goes beyond mere modification. His plan to strap Woody and Buzz to a rocket and launch them to a fiery death isn't the most complicated villainous plot, but for toys, it's about as final as it gets. Fortunately, it's easily foiled, even if it takes absolutely traumatizing a young child by revealing the secret life of his toys to do it.

Angelica Pickles embodied the kind of evil of which only children are capable

Look, Angelica Pickles never tried to conquer the world or commit mass murder, but graded on a curve for her youth and that of her victims, she may be the most perfect villain on this list. The primary antagonist for the babies of Nickelodeon's Rugrats, Angelica was selfishness and spoiled-brat behavior incarnate, with a streak of devilish cunning that allowed her to manipulate the adults in her life into thinking that she was a good egg. As the cousin of main Rugrat Tommy Pickles, she was often tasked with babysitting the toddlers, which gave her ample opportunity to get up in their business for her own amusement, from breaking a lamp or framing one of the group for her own misdeeds.

Of course, like the best pop culture villains, Angelica has a complex back story that explains her evil ways. An only child, she was spoiled by parents who, thanks to their demanding careers, were rarely around to give her the attention she so craved. She was even softened over time, thanks to Rugrats co-creator Arlene Klasky's discomfort with how Angelica was depicted in the early seasons. Still, she remained a constant source of trouble for the show's leads, always ready to take advantage of a group she thought of as "dumb babies."

The Joker was never funnier, or more fiendish, than in Batman: The Animated Series

A lot of talented actors have taken on the mantle of the Clown Prince of Crime, so it's somewhat surprising that what many fans think the definitive version of the character came in animated form. That's thanks to the vocal talents of a man whose best-remembered role was decades prior ... and who was actually a backup after Tim Curry didn't work out. 

Seriously, if Bruce Timm's Batman: The Animated Series was remembered for nothing else, we'd recall it fondly for giving Star Wars hero Mark Hamill a second shot at stardom, which the actor dove into with a madcap relish that provided the perfect funhouse mirror for Kevin Conroy's dignified, subdued Bruce Wayne. Fortunately, that's not all the show had going for it, as it also provided a mature, nuanced take on the adventures of the Caped Crusader.

It wasn't, however, all fun and games. The difficult part about bringing the Joker to life is that the character needs to be able to tread the line between terrifying and hilarious, making them feel like — with apologies to Two-Face — two sides of the same coin. Hamill's take could certainly be hysterical, but it also made no bones as to the character's homicidal mania as he sowed anarchy and pain in Gotham City. The laugh, alone, could send a chill up your spine. Whether he was torturing Tim Drake or psychotically seducing Dr. Harleen Quinzel, Hamill's Joker did it all with a ghastly glee that no other Joker has been able to match.

Oogie Boogie was one of the scariest animated villains of the '90s

Leave it to Tim Burton to craft a villain who — even in a movie filled with every form of ghoul, ghost, and monster you can imagine — sticks out as the stuff of nightmares. That's Oogie Boogie, a bogeyman made of sack cloth who takes Jack Skellington's semi-innocent kidnapping of Santa Claus and turns it into a life-and-death struggle, torturing the Christmas icon and the lovely Sally. He has a haunting lair full of booby traps. He sings like Cab Calloway. He can project his shadow on the moon. Oh, and also, he's literally made of bugs. Gross.

Not a part of the original Tim Burton poem that inspired The Nightmare Before Christmas as a film, Oogie's creepy design came from a sketch the filmmaker made of a potato sack man filled with insects. The stop-motion puppet that would bring him to life was a testament to his imposing nature, standing a full two feet tall, twice the height of the other characters. It's his sadism, though, that really puts him over the top, separating him from the macabre but otherwise charming, characters who make up the rest of the movie's Halloween Town residents. It's kind of implied that he also has a gambling problem, which is a bummer to be sure, but no excuse for strapping Santa to a giant roulette wheel or cooking anyone in a snake and spider stew.

Mr. Burns has been taking capitalism to its extremes for 30 years

Every citizen of Springfield have gotten up to some sort of shenanigans over the course of The Simpsons' decades-long run, but there's only one who's cast a long, hunched shadow over the town — once, literally. That man is Charles Montgomery Burns, the embodiment of corporate avarice. As the owner of the nuclear power plant where Homer Simpson works, he's had ample opportunity to make that character's life hellish, but his unquenchable thirst for wealth and power has led to him negatively impacting any number of other Springfieldians. He's not above crippling a child to advance his agenda or slaughtering puppies so he can use their pelts to craft a suit. He even tried to take candy from a baby, although he kind of paid the price for that one.

Of course, this being a comedy show, Mr. Burns is also pretty hilarious, with plenty of plays on his indeterminately advanced age and physical frailty. His catch phrase, a muttered "excellent," became a go-to quote for anyone hatching their own evil plan, and he's even been shown as sympathetic from time to time, albeit briefly. With an army of sycophants willing to do his every whim, Mr. Burns has done some truly horrible stuff. He's gone so far as to block out the sun, and while his plans usually get foiled, his bottomless resources means he'll always be back to serve as the eternal thorn in Springfield's side. It really makes you want to say "boo-urns."