When it comes to writing, different people do different styles well. No style is easy be it reflective or expository or informative.
Writing to entertain can take various forms but the most challenging to pull off, according to me, is the humorous.
Why?
1. When the joke falls flat: You’re always taking a risk with jokes. Nothing fails so badly as a joke that fails to be funny. You end up worse off than you were before if you’ve insulted someone or if the piece had nothing else to recommend itself than the humour.
2. When the joke is taken seriously: When readers read quickly, they don’t catch the subtleties. In an older post, I happened to say that we are in a “post literary age.” The irony escaped quick readers who took it seriously and I ended up meaning exactly the opposite of what I intended. I’ve seen readers mistake articles in The Onion for real news but that’s probably a different story.
3. When the object of fun does not have a sense of humor: This point requires very little explanation. It’s hard to justify humour when everyone involved does not appreciate the fun. By the nature of the style, being funny often involves an object of fun unlike other kinds of writing.
4. When you can’t handle the sentence length: I’ve seen that if you believe brevity is the soul of wit but fail to pull off the joke, you come off as smart aleck-y. If you use long sentences overloading them with irony or word-play or too many qualifying clauses as part of the joke, you end up with clunky sentences that are not funny anymore. Fun requires the light touch and no handbook can teach you how to write funny sentences.
5. When shared subtleties of a culture escape the audience: Jokes that are immediately appreciated in one cultural setting or in a set of people who speak the same languages fall flat in a different setting or may even seem politically incorrect. If you’re trying this kind of humorous writing, you have to be super careful or stick within a certain community.
6. When shared values of a time are gone: When I watch old TV shows I find gay jokes or “taming of the shrew” style jokes about women that just don’t seem funny anymore. The fun has sort of evaporated with the times. But there may be equally hurtful jokes circulating in the present eliciting laughter which tell me we haven’t necessarily become better people but that those sensibilities have changed (fortunately in these examples).
7. When you don’t consider taste: There is “in your face” humor, gentle and subtle humour and a million other styles that you can adopt. But unlike reflective or expository writing, the audiences for different kinds of jokes might be mutually exclusive so that the “market” is divided so to speak. You have to know very well who you’re appealing to and who you’re not. So one section will love you and the others hate you.
The humorous style is the most difficult to pull off because it has the least rules that lead to success and is the most difficult to control.
It also has a paradox embedded in it. When, as a writer, you run out of humour, you become tragic.
bottledworder 
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