Stop Making Sense: Questions Need Answers, No?
Silly is never silly.
When you think about humor, you instinctively want to say, "Oh, stuff that makes me smile or laugh. Sometimes it just makes me happy."
Why does it do that? At some level you see what the writer was trying to say. You may be seeing something you've never seen before. You may have the rose-tinted glasses removed from your eyes.
What makes things funny?
Humor is one of the most individualistic forms of communication. What I might find funny, you may not.
While millions of us may end up owning the same comedy album, video, or book what we take from it is our own. Monty Python to a Texan is probably an entirely different animal than it is to a Londoner. In fact, it's also something totally different to people today than it was 40 years ago when it was new.
Stop Making Sense
I have to admit, that the majority of time what people seem to find funny in my writing is just my phrasing. I've heard people chuckle at things that I thought were dry and boring. A lot of it comes from long exposure to funny people. I wrote a hub about 5 writers that I find funny. Repeated exposure to funny things may not make you funny, but it can't hurt.
When I intentionally try to be funny, it's often harder than if an idea just strikes and strikes right. Hemmingway wrote that the hardest thing about writing simply is to remember how complicated things were. You have to remember that funny may be far harder than straight prose. Plus, what you find hilarious others may not understand at all. What you meant in a totally non-offensive way may be misconstrued.
Questions without Answers?
I've actually found the Questions and Answers here at HubPages have been an invaluable tool. When I see a question, I may know the answer that the asker seems to want, but my brain almost always gives some sort of quirky answer. I almost always run with the strange answer.
Sometimes I ask a question that I think is quirky, but get a good, straight-forward answer that makes me stop and think more about what the answerer is saying. I think the best example of this is when I asked, "How high is up?" That's a traditional stupid question if ever one has been asked.
The answer that stuck in my mind though is "62 miles, that's where the Earth's atmosphere ends." That's a pretty good answer to a really bad question. That's what I've tried to do, give good answers to anything I've answered. My definition of good may not be yours. If you're looking for a deep philosophical answer, I probably won't stick my oar in. If you've made the mistake of asking a political or general question, get ready for the waves.
Humor, by definition, isn't offensive.
While some comics have gone out of their way to be offensive--Monty Python once pointed out that the purpose of The Meaning of Life was to offend everybody--most aren't trying to offend. Looking at things differently may shock some, but that isn't the goal.
If you offend everybody, nobody gets your message. If your message is, "Hey automakers, quit giving stupid names to cars," you have to do it slyly and quietly. You can't show up at Toyota's doorstep with a sign that says, "Sequoia's a tree, not an SUV!" Actually, that is kind of catchy, though.
Anyways, I think this is sort of an apology to those I may have offended with my Answers. In the words of the German from some episode of Black Adder, "Many appy lowgies. Byeeeie!"