For the folks offended by various words and phrases and stereotypes etc. What do you think of stand up comedy or vulgar comedic movies?
Serious question. Do you just not ever go or you think it's OK in that context to offend or what?
It's not hard conceptually, it's just subtle. Fundamentally, it is about power. Making fun of people "below" you in the social hierarchy is bullying and so not funny; making fun of people above you in the social hierarchy is subversive and so can be funny. And making fun of yourself or your own group falls into the subversive/funny category.
The other aspect is that comedy has to be unexpected. Jokes based on stereotypes aren't funny because there is nothing unexpected about them -- like, really, that's the best you've got? OTOH, flipping stereotypes is unexpected. The best jokes reveal a truth that the audience never noticed before -- think of Chris Rock on the difference between "rich" and "wealthy."
Best example I can think of is "Blazing Saddles" (one of the funniest movies ever made). Plentiful use of the word "nigger," but used to mock the idiocy of the people who would call a powerful black man a "nigger."
To my mind, I don't personally care much about hurtful words, because it says more about the speaker than about the person/group he is referring to. Hell, I am foul-mouthed and detest euphemisms myself; there are no sensitive ears here that require protection. But I do object to disparaging words when deployed by people with power against people without, who cannot defend themselves or strike back -- like, say, the boss calling his underlings "gals" and expecting them to get coffee (flashback to "9 to 5" here). In many instances, it's just largely cluelessness (that particular boss was probably trying to avoid saying "girls" because he knew that was bad, but thought "women" sounded too formal and so chose "gals" thinking it was the most comparable to "guys). In that case, I'm most likely to respond along the lines of "dude, you know what that sounds like, right?"
OTOH, someone who is well aware that a particular word hurts but insists on continuing to use it is just a bully and an asshole.