Genuinely funny villains are probably more rare than they should be. I suppose it relates to the idea that villains are supposed to be scary or detestable, and a good sense of humor tends to have the side effect of making a character more likeable. In order for a villain to be both effective and funny, that humor has to feed into their evil in some way. Of course, this still has a tendency to make the villain in question likeable, but at least it serves the dual purpose of making the viewer a bit uncomfortable as well. Which brings us to Hellsing‘s Jan Valentine.
Jan is part of the vampiric mercenary squad known as the Valentine Brothers along with Luke Valentine, although given the fact that they look nothing alike, even having different skin tones, it is hard to say if Jan and Luke are actually related in any way. Both are moderately powerful vampires with great skill in firearms and strategy. Jan seems to be preternaturally agile and resistant to damage, as well as able to carry and fire two assault rifles at once with little concern for kickback or aim. He is also obnoxious in the extreme, constantly taunting, laughing, and cursing at his opponents, though whether this is to throw them off balance or simply part of his nature is hard to say. In most two man groups where one is the talker and one is the professional, the professional usually ends up coming across as the more well-liked, but as the Valentine Brothers go, I find Jan to be far more interesting than Luke. I attribute this to just how far he takes his trash-talk. There seems to be no limit to what horrible things he will say, whether it be announcing how “fucking hard” he is while committing mass murder, or telling a group of trapped victims he is moving towards that he recommends they start pissing themselves, followed by praying to their impotent god. He’s quite hilarious, until one takes a step back and realizes how awful he is.
Jan doesn’t really have much stated motivation for his misdeeds. My interpretation is that he’s a thrill-killer, who probably looks at life as one big video game where he can have the most fun and get the highest score by slaughtering people and drinking their blood. There is little information on who he was or what he was like before he became a vampire, but chances are he was either a degenerate or an XBox Live player who, upon being freed from mortality and morality, decided to just live like nothing meant anything. Underneath Jan’s joking exterior is a pretty vicious nihilistic streak, the laughter of a man who finds everything hilarious because he feels no connection to anything whatsoever, and the deaths of the people in his wake are consequently the equivalent of slapstick to him. Even in his own death, Jan finds humor, laughing maniacally as he burns away to nothing, and flipping off Sir Integra as he does so.
Jan lives a rather short life for a villain on this list, surviving only two episodes of the series. This is probably for the best. The candle which burns brightest usually burns shortest, as they say, and his extreme personality would probably begin to grate after too long. Nonetheless, Jan makes those two episodes his own, imbuing them with a heavy mix of personality, humor, and horror, not to mention numerous quotable lines. Toward this end, I will provide not one, but two clips of him, from both versions of the Hellsing anime series. Due to his ridiculous swearing, these are NSFW.