How far the jokes...and where does the freedom of speech stop

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Recently, we had a comedian who put his foot in his mouth, coming up with obscene and crude remarks on parents and sex. There is an outrage, naturally. I have unfortunately not come across the controversial content. Nevertheless, I do feel that it is an art to make others laugh. It requires knowledge, it requires quick thinking, consideration, empathy, and what has been termed by somebody as "artless art of repartee". Not everybody is equipped with that. Indeed, it is difficult to come up with jokes, simply because others expect it of you. It has to come naturally like pee. (How obscene can I get). And these podcast folks are humans too. They have their preoccupations with family and other jobs. So .. expecting humor, just because I am paying for it, is ...unrealistic and unreasonable. That said, when do we say line is breached? As one of the judges pointed out, when a joke is repeated too often, it soon loses its sting..and gets accepted as norm, even if it is hurting somebody. But the freedom of speech....where do we stop that... 1. Cautious not to hurt anyone directly or indirectly. Personal level jokes - we never know when they will hurt someone. Many insufficiently educated people feel the peer pressure to come up with something, and end up cutting personal level jokes. These are, in fact, ridicules. 2. Punishment for raking up riots. It can happen if the jokes are targeted on specific community. I too tease the Americans, but luckily, they have evolved to have some sense of humor. The same is not true of uneducated and under educated folks in India, so it is easy to brew trouble...unwittingly. 3. Usage of subtleness to increase the sense of humor of the under educated. 4. No trespassing the truth in the name of art. 5. Willingness to apologize, and not justify the actions. That is about it....right to exercise freedom of speech....responsibly. Is it so difficult to know where to draw lines?