Harry Mudd kind of is like the Joker... from the Silver Age.
Both start off more serious (Mudd was a space pimp at first and the Joker actually killed people back in 1940), then they quickly become pranksters who aren't doing things that are really that bad. And, at the end of each story, they go to jail, and everyone has a big laugh. And we all know they'll escape again.
Makes me wonder what Harry Mudd would be like if they made him darker and edgier. Like what happened with the Joker.
DIS kind of touched on this.