Audiences like being challenged with risky material, as long as you make them laugh.
For a comedian or comedy writer, hitting an audience with offensive or controversial material is an advanced move. Everybody wants to do it because it’s advanced, but don’t be too eager. Learn to walk before you fly.
When you’re ready and you’ve earned some confidence, how do you offend without angering the audience?
Six ways:
Build rapport with them. Show some vulnerability or a “hey, I’m just kidding around” vibe. Tell some relatable jokes first. If you build some rapport, you can burn some of that capital offending, as long as you make them laugh.
Be aware of how you come across. As a performer, this is something largely out of your control. Do you look like a jerk or a pushover? A conservative or a hippy? Once your audience gets a sense of who you are, they’ll show you what your parameters are if you read them carefully.
Love them. Whatever group you’re offending, be sure to show that you care about them as human beings. If there are any in the audience, speak to them directly.
Make them a part of a joke. If someone is marginalized, or identified as part of a marginalized group, they want to have fun too. Tell jokes they can relate to and enjoy. If they’re used to being excluded but you include them, they’ll love you for it.
Don’t express a strong political opinion about the offensive material. Make sure you’re mocking everyone on all sides of the opinion spectrum. (Except Nazis—say whatever you want about them.)
Make them laugh.
Number 3 is tough one -- love thy enemies. Are comedians supposed to be saints too?
This is a great piggyback to the Getting Cancelled piece. Along with Nazis, I think we can say anything we want to Flat-Earthers.