I think if they did, she would end up like Venom in the 90s, a perfectly good villain who is turned into an anti hero to give him or her their own title and becoming less interesting in the process. Typhoid Mary works as a villain, a sympathetic villain perhaps, but a villain all the same, its a shame that so many great villains are turned into anti heroes, it means less great villains.
Jester has a huge problem, he was made as a rip off of the Joker in the Silver Age. Making him more sinister would make him just seem like a rip off the modern Joker. So what do you do with him? Try to highlight any difference between Jester and Joker or Trickster or Toyman or any other similar type of villain. I think Jester's career as an actor is the key to making him unique, that is what should be highlighted and think giving him someone in his past who wronged him and ruined his acting career, gives him a story that would be different from a typical Joker story.
The original Death-Stalker is dead, he was brought back in a recent mini, only to die again, it might tricky to bring him back again. However there is a new female Death-Stalker working for Purple Man.



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