At risk of implying that Asshole Skepticism is largely about getting a laugh - far from it, being factually accurate IS paramount - I continue on on the track of things I learned about being funny when I was officially in that business. At some point in the not too distant future I'll get more specific ablut how and when humour in skepticism is appropriate and/or a recommended strategy.
Early on I realised one important thing, never waste a moment asking yourself whether something you might say is witty or not. Just say it. You will find out immediately whether it's funny or not. If you wait, the moment will be lost and it WILL NOT be funny.
Once you get in enough practice doing this you'll find that you are start saying things even before you've thought them through... do not panic! Just let your instinct carry you through... just say it!
The simple fact that you 'thought' to say whatever you have said so damned quickly will often make it seem funnier. Yes, you will occassionally get laughs for things that upon further reflection aren't really that funny at all. That's just fine. People laughed. They register that as you being a funny person - that means they'll be far more likely to laugh with the things you say, 'cause they expect you to say clever things.
Inevitably, whether you are percieved as funny or not, you will sometimes get laughs, and sometimes you won't. This is where confirmation bias really springs to your defence. When you aren't funny - so long as you don't say something appallingly offensive instead - people will hardly notice. They may not even realise you were trying to be funny. But when you do manage to come out with a killer zinger, they remember that. Some people have a distinct "I'm telling a joke now" tone that enters their voice when they are trying to be funny. It's not that that tone makes the joke not funny, it just helps call attention to the myriad times when the joke isn't funny. I am very confident that this is why 'dry' people are often seen as so funny - because when they are funny you REALLY notice it.
I'm going to finish with a brief anecdote:
Months back at Skeptics in the Pub it was a relatively small night (I think actually it was at the time a 'big' crowd, but since then the average attendance has dwarfed that night.) one of the regulars and a very interesting one-timer got in a very spirited debate in the centre of the room. It was impossible to ignore their discussion, and as far as I was concerned, you didn't want to miss it. They were both 'on.' The discussion danced around the outer-edges fo my ability to follow along let alone participate and it seemed as though most people there were in the same situation. What we had was two philosophers challenging each other's position on specifics of atheist thought. It was fascinating. They were both eating it up - revelling in the organic heated debate with a worthy mind. If it had gone on all night it would have been too much, but as it was it was an SitP highlight I will probably never forget.
After quite sometime of back-and-forth with only limited input from other people the two of them got into an exchange that was made up of quotes. I've actually forgotten the specific quotes, and I'm not going to do the research to make up a plausible argument/counter-argument that would lead to the same place it did that night. After about two quotes from each debater, each countering the other's point, and the listening crowd hanging on the tension before I even realised I was doing it leapt in with one of my own: "'You can't reason with Jesus freaks, otherwise there'd be no Jesus freaks.' Dr. Gregory House, M.D."
It was really only tenuously connected, but it brought down the (ahem) house. it broke the tension and ultimately wrapped up the discussion at about the right time - they weren't going to come to a conclusion any time soon and they had definititely hit a climax. They gave each other a delighted and respectful shake of hands agreeing that it had been a lot of fun to 'go at it.'
That discussion has come up a few times in other discussions at SitP - always mentioned as a highlight. I've never heard anyone quote the debaters. They all quote Hugh Laurie via me.