14. Herman
20th Century Fox TelevisionDid you even remember who this was referring to when you read the name? If you didnt, its not really your fault because Herman really isnt that memorable or interesting. He is one of the characters who appeared in multiple episodes early on but got gradually faded out because, by that time, the show introduced newer, better characters. He is not the only one in this list in this situation so, for the sake of brevity, lets just call it Herman Syndrome (Google says that that's actually a real thing) Herman Disease it is. Another problem with his character is that the writers dont appear to know exactly what Herman is about either. At one point, he is a (relatively) honest dealer of military antiques, another he is involved in selling counterfeit jeans and in another he takes Chief Wiggum and Snake prisoners and puts ballgags in their mouths for some fun, Pulp Fiction-style. Not even the idea for his own recurring gag worked out: in the commentary, Matt Groening mentions that the initial plan was for Herman to give a different recollection of how he lost his arm each time. However, this idea only lasted for one gag because the second one was cut during editing and the writers decided to drop the idea altogether afterwards.