If you’re a comedian or someone in any other field who wants to push some boundaries let me make something perfectly clear. The trick is to go against the prevailing system, not simply discuss a “controversial” subject (and certainly not to discuss it in a way that enforces prevailing norms/power structures). If you want to make a joke about, for example, rape, make it a joke that undermines rape culture. Ridicule our ridiculous acceptance of violence against women as expected/acceptable. If you want to make a joke about race, make it a joke that undermines our racist culture. Ridicule our ridiculous acceptance of and blindness to everyday discrimination. Really, the only way to push boundaries is to make people uncomfortable and enforcing dominant attitudes does exactly the opposite.
Your jokes CANNOT be at the expense of the minorities/oppressed group. That’s not to say they can’t be at the expense of the oppressor.