Demon Castle Special: I'm Kid Dracula
The Castlevania series has always had a sense of humor about itself. Although many of the games lean heavily on the Gothic genre tropes, there's always been a sly eye towards the silliness of the common devices. Take, for instance, the parody credits at the end of the original game (Belo Lugosi, Christopher Bee, etc. for the monster's "names"), or Portrait of Ruin and the cream pies and paper airplanes for weapons. The games are serious, but even the game makers liked to have a little fun with their series once in a while.
From that perspective a game like I'm Kid Dracula makes perfect sense within the series. Although offically not a part of the continuity -- itself being a parody of the series (that kind of started as a parody, so a parody of a parody), the game was officially known in Japan as Demon Castle Special: I'm Kid Dracula (with the "Demon Castle" being part of the official name for the Castlevania series in Japan -- Demon Castle Dracula). In many ways it's of-a-piece with the greater series -- the character, Kid Dracula, starts off in his castle and has to go venturing out into the lands to face down a challenge from a rival villain, Galamoth. The game literally starts you off in the Castle Keep of Dracula's castle, the same keep the heroes are always fighting to get to normally. Everything about this game say's "this is Castlevania but, you know, for funnies!"
Although the game originally didn't come out in the states, it was eventually ported (as a sort of remake-come-sequel) to the Game Boy as simply Kid Dracula. Even then, it wasn't announced as part of the Castlevania series, instead being called simply I'm Kid Dracula (thus why we call it that on this US-centric site), so many Castlevania fans (the editors of this site included) missed out on the game during it's initial release.
Which is a tragedy since, aside from the fun, funny attitude this game as towards the series, it also had a few notable lasting impacts on the series as a whole. For starters, the character of Kid Dracula is, in actuality, Alucard. This was one of his first staring roles (and followed Castlevania III, Alucards offical first role, by only a month). Although not officially in continuity, it's not hard to imagine this game (and it's Game Boy "sequel") taking place in the early days of Dracula's life (which has it's own, rather convoluted timeline by this point), before most of the official games take place. The Kid Dracula version of this character also showed up in other Konami games (like the Parodius series of parody space-shooters)
More important, still, is that the I'm Kid Dracula sub-series introduced Galamoth, a special boss in Symphony of the Night and a soul to collect in Aria of Sorrow. Galamonth then returned s the driving villain behind the events of Castlevania: Judgment -- and all that spawned out of this one little game.
So it's weird, then to think of the influence this game had on the series a parody game when it doesn't actually fit into the official series. Were a game like this released now it would probably be as special download for consoles (XBox Live Arcade or Wii U Ware or something) and might have had a larger market than the original, Japan-only release. But then, it's hard to know if Konami would release a game quite like this again. It's been a long time since this game came out (and nearly as long since Konami was interested in creating parody games). For now this game shows as the best weirdest little one-off (two-off if you count the game boy game as a true sequel) showing the kind of fun Konami could have, and mayb the kind of fun they might be able to get back to, one day...