Being in charge isn't a simple task. It’s a job that a lot of people want until they discover the things that come with it. In the world of superpowers, things get trickier than they do in the real world. Leaders come with a different kind of baggage and things are more dangerous. For instance, you could be forced to work with Bullseye or Sabretooth. Guys who are known for being murderous and backstabbing.
Working for the wrong person can get you and your loved ones killed. The Riddler is a lunatic who’s with a reputation for slaying his henchmen or driving them crazy. On the kinder side of villainy, there’s Catwoman. She’s not just a boss. Selina Kyle is a teacher as well. Two characters with opposite styles that work for certain people (somehow Riddler keeps getting Henchmen). Nevertheless, both of them could end with your death. These are only two examples.
Here are fourteen fictional characters and what it would be like to work for them.
This is the last person you’d want to work for. He’s a psychopath with with zero regard for anyone. That sometimes includes himself.
Let’s take physical harm and death off of the table. Working with the Clown Prince of Crime will leave lasting mental scars. DC Comics fans have seen the verbal abuse he’s unleashed on everyone he’s worked with (for example, Harley Quin). Plus, even if you complete your goal, he may kill you just for a laugh.