1. Negaduck from Darkwing Duck.
Negaduck is probably the most badass villain on Darkwing Duck. I mean, boyfriend IS just an alternative version of DW after all. He's also the leader of the Fearsome Five, and is definitely the most evil person to ever terrify the fair city of St. Canard.
2. Team Rocket from Pokemon.
Team Rocket is definitely the most adorable group of villains on this list. I mean, they shouldn't really even be classified as villains since they haven't ever been successful in doing anything "evil". But they're so cute with their matching outfits and talking Meowth and long motto that a large part of me always kind of wants them to catch a break and steal that Pikachu once and for all. And what's their story anyway? Lots of people claim that James is gay but sometimes you'll catch a moment between them that's filled with sexual tension. Are they or aren't they? Will we ever find out?
3. Sideshow Bob from The Simpsons.
The last thing you hear before you die: show tunes. Say what you will about the quality of The Simpsons in recent years, but you can't deny that episodes with Sideshow Bob are always top notch. I mean, dude is voiced by Kelsey Grammer! I'm pretty sure that man was created for the sole purpose of providing voices for cartoon villains. I mean, he's voiced other kind of characters, sure, but they all sucked. I wonder why Kelsey Grammar doesn't narrate things the way Morgan Freeman does. He should.
4. Hexxus from Ferngully.
Holy shit, where do I begin? I didn't watch Ferngully for nearly 10 years because Hexxus scared me so much. What the fuck is he anyway? One minute he's a sludgy skeleton, and the next he's this singing cloud of gas. Hexxus is voiced by the one and only Tim Curry. And he sings a song about pollution and I gotta say, for a children's movie, it's pretty sexual. That's kind of ridiculous. I mean, the film's whole message is about how we need to preserve the environment, and yet they make pollution sound like the sexiest fucking thing in the whole world. I'm not even kidding! You can listen to the song here.
5. Dr. Reginald Bushroot from Darkwing Duck.
Dr. Bushroot makes me sad. He wasn't evil before he became half plant-half duck. He was always picked on by his colleagues and so after his accident, he had a lot of built up anger issues and thus became a villain (see kids, THIS is why you shouldn't bully others). I think it'd be super sweet if he was in a movie where he had to battle Hexxus. Remind me to write that screenplay later. Anyway, it disappoints me that he chose to use his plantlike abilities for evil rather than good. Who doesn't like a man that likes flowers?