A lot of it is knowing your audience. If you're midway through a story and you can tell it's shit -- we've all been there -- a) you misjudged your audience to begin with, probably, and b) for god's sake don't finish the story, find some way to defy expectations. You've also got to know when to laugh along with what you're saying and when to deliver it straight-faced. Both can save jokes that seem headed to hell. This is huge, knowing your audience if you are dealing with a small group of individuals is fundamental to getting a real laugh (not to be confused with a pity laugh; you know those chuckles people throw at the guy who is trying too hard). If you are dealing with 1 or 2 individuals I stick to safe ground jokes until I get more familiar with them. This comes from experience, I have seen people go in hard with jokes early, misjudge the audience and it just doesn't work... The opposite of this and one of the easiest places to get a laugh (IMO) is when you are in a large group of strangers and there is that awkward early phase (i'd love to try stand-up but I cant write jokes). As an example, I recently attended a training session in a different country and we had to do some silly task on the first day involving company logos. One of the trainers (formally dressed, strict woman with a goal on running a 'tight' training course) approached me and asked: "I just wanted to ask are you familiar with that company logo? Do you guys have Starbucks in Ireland?" My response: "We have Starbucks, we also have running water and electricity, indoor toilets are planned to arrive next year" pretty much ground the room to a laughing halt for the next 5 minutes. It was an easy joke to deliver as the room, audience, trainer and context all worked together to help me. Reading that it might sound very sarcastic but I softened the delivery and presented it as a semi self deprecating joke complete with apple eating grin. If I went with a straight sarcastic delivery then the trainer would have felt awkward, the room may have divided in support for her and the moment would be lost. Its fluid, you have to take a chance sometimes but sticking a warm smile and being friendly will keep you out of trouble when you get it wrong. Don't be a smart ass taking pot shots, that's just getting cheap laughs and anyone can do it. Break with convention, spot the story being put forward and undermine it but do it with style, charm and a warm smile. The goal is to come off like a funny, relaxed person who wants everyone to enjoy themselves; everyone will get on-board with that and laugh with you. If you sit back and make smart ass comments and you do it from a bitchy place then you will run out of audience patience very quickly.