25. Dr. Horrible
Appeared in: Dr. Horrible's Sing-A-Long Blog We're starting this out on a light note: Dr. Horrible is probably the newest character that can be considered part of the Whedonverse - and is the single greatest singing supervillain with his own blog ever imagined. Created as a web series during a writer's strike in 2008 which kept Whedon from working on other projects for a bit, Dr. Horrible's Sing-A-Long Blog was something new and absolutely unique: a web series done as a musical, told from the perspective of a not-so-super supervillain hoping to make it big and get into the "Evil League of Evil" with a couple of well known actors anchoring the action on-screen (Neil Patrick Harris as title character Dr. Horrible, and Nathan Fillion, whom Whedon had worked with on both Firefly and Buffy, as his arch-rival, the superhero Captain Hammer). There was, of course, a love story mixed in, and the girl for which Dr. Horrible pines (Penny, played by Felicia Day) winds up dating his nemesis, motivating him even further and spurring on his attempts to impress Evil League of Evil leader Bad Horse (yes, he's actually a horse). NPH absolutely shines as Dr. Horrible, and he parleyed what should have been a funny, one-off character into something more. Dr. Horrible (NPH in character) managed to interrupt the Emmy awards in 2009 (in reality this was a sketch with Dr. Horrible and Nathan Fillion's Captain Hammer, which gave Dr. Horrible an even wider audience), where the web series had won a Primetime Creative Arts Emmy Award. Dark Horse Comics also released a comic of the property, which included an origin story for Dr. Horrible, and the show was a smash hit on DVD (sold exclusively via Amazon, originally). Dr. Horrible works so well simply because he's relatable: despite his quest to be the best evil-doer he can be, his fears are our fears: his inability to talk to a girl, his hesitance to approach her, the humiliation he feels when someone "better" for her comes along - in a very real way, Dr. Horrible is a regular guy, who just happens to be a practicing supervillain.