This is a work in progress. I will share this with some of my students and friends who I've talked comedy with and try to get all of the helpful advice I can packed in here. So come back, and see more added until I decide it's done and remove this message.
Here are some rules and guidelines I have developed over a decade plus of writing and performing stand up comedy. Every "Rule" I've observed is broken by someone who succeeds wildly anyway. The rules are for when it doesn't work and you want to know why. Ask yourself what rules you're breaking and then ask yourself if you're breaking that rule on purpose and if it's stopping the bit from working. If you want to keep breaking the rule that is getting in your way, you'll have some work getting around it. So these aren't hard fast rules I expect anyone to follow, they're rules I think you'd be wise to be aware of and the have fun playing with and breaking.
"Brevity is the soul of wit."
Probably the best thing ever written about comedy. Keep it short, keep it efficient. Sometimes the efficiency itself is the joke. Hearing a complex thought explained succinctly can be a thrill.
There are long jokes that work great, of course. I like to think of it this way; every word in a joke is weight. The punch line has to carry that weight. The more words, the stronger that punch line needs to be. Little laughs on the way to the punch can also throw a bit of weight overboard.
Wait for it... wait for it...
Give your punch line a chance. You tell your punch line and then they laugh, if you wait for them to laugh. There is that pause before they start laughing, that pause while their brain processes what was just said, and/or makes sure you're done. That moment is when we face the terrifying prospect of them NOT laughing. Pesky self preserving instincts will often see a comic throw in some words here to cover their ass. Words that say, "No, I wasn't pausing. I didn't expect you to laugh there, ha ha, nah, that wasn't even the joke." Sadly this steps on the laugh and kills it. One MUST have the confidence to take that risk. And next up is a tool to give you that confidence
How To Bomb
Knowing what to do when they don't laugh helps a-lot in having the guts to risk them not laughing. Having a joke bomb can actually be a gift. I like the definition of comedy "Creating tension and relieving it in a surprising way." When a punch line doesn't get a laugh, there's your tension. It's a very real tension too and anything you do that says to the audience, "It's okay. I'm alright. We're good." will be a huge relief. When a joke bombs a line as simple as, "Yeah, that bombed." will get a laugh, every time. Of course, you should have some fun and come up with something better and more unique but you want to recover and give your next joke a fair show, so use that if you need to use that. I have seen comics win an audience over, really get the audience on their side, without a single joke working.
Homework: Watch the late night talk shows. The monologues they turn in are gonna feature a lot of bombs. Along with their writers they have to churn out a lot of comedy and they don't get a chance to test it at an open mic, and rewrite, and try it again, and do it at a showcase, etc. So, they bomb a lot of jokes and get the biggest laughs they get out of dealing with these bombs. Johnny Carson was the master of this, swinging the golf club, knocking on the microphone, blaming the writers.
Open Mics are Invaluable and Horrible
If you're thinking of trying stand up comedy. Go to an open mic. Seeing people at all different skill and experience levels really humanizes comedy, especially if you've mostly seen the best of the best performing on television. And being there in the crowd, for me anyway, made it feel do-able.
Performing at open mics is the way it begins and mostly, it sucks. You get five minutes if that, and it goes by too quick and the audience is bored, or exhausted or just made up of other comics or all of the above. Do it. And do it again. And occasionally it'll be awesome. When at last you get to perform at a showcase or opening for a touring headliner you'll be amazed at how much easier it is to get over. So keep pushing through and build them comedy muscles.
It's not just a sappy love story, it's also a comedians most valuable tool. Whether it be an actual notebook, your smart phone, whatever, write down every funny thought that occurs to you. Most every comic I know has that memory of that one joke idea that they were so sure was the best joke ever but by the time they got a chance to write it down... they'd forgotten it. All they remember is that it was gonna be the one that made them, the one that would make the whole world laugh so hard they'd forget to wage war, the one that would save us all and bring harmonic balance to the universe. The ghost of that joke will haunt them forever.
And be organized. I had a comic friend who was blowing important gigs because he was just doing whatever jokes he could think of in the moments before he went up. When he actually sat down and reviewed his years of notes and made a list of all his jokes he not only had a much better A-list set for auditions and big gigs, but he was surprised to find he has a pretty solid hour, at least 30 more than he thought he had.
Notes On Stage
Better to have them handy and not need them than to need them and not have them. Better to use them than to try to go without them before you're ready. I see professional headliners stash a set list by their beer all the time. They tell a joke and while they give the audience a moment to laugh they step back, sip their beer and see what joke they wanted to tell next. Part of this working is giving your jokes a short name so the list can be efficient and easily read at a glance, and put your jokes in a logical order so you remember what triggers what.
The Punch Comes at The End
It's surprising how easy it is to mess up this seemingly obvious bit of formatting. Know your punchline. They're the words that make people laugh, the words that relieve the tension, the surprise, the twist. Make sure you've structured your joke so they are the last words you say. For the why of this one, see "Wait for it... Wait for it... " above.
We have no problem with Superman flying, outrunning bullets, being impervious to bullets, leaping tall buildings in a single bound and all that. What we have trouble with is Jimmy Olsen and Lois Lane not recognizing him when his costume consists of a pair of glasses.
We're given a reason to believe those other things. He's from another planet. He's not human. We are not given a reason for Jimmy and Lois, two journalism professionals, being so clueless. And so we scoff.
You don't have to tell the truth, but you do have to be believable. Emo Phillips really stretches this, with his outrageous tales but they work largely because he presents such an outrageous character to begin with. We can suspend disbelief when we look at his hair, clothes, body and when we hear his voice.
I've seen really good bits get thrown off by an outrageous aside and more often than not, it can be fixed by just presenting the outrageous thought as a fiction.
Example: Um... hang on. I'm gonna come with a good example I promise.
Look up, not at your feet.
(Unless you're Mitch Hedberg, in which case you're dead.)
Anatomy of a joke (explaining tags)
Paranoid works well to illustrate this
How not to be an asshole
Who is the butt of the joke? Are you laughing up or laughing down? When doing crowd work, are you picking on the easiest target in the room?
Woody Allen, Bob Newhart, Rodney Dangerfield all had a stage presence that was enhanced by them embracing their nerves, stutter, big ol' sweatiness. If you can't beat it, make it a strength. Be who you are up there because fighting it will be distracting.
Don't say car. Say Toyota Corolla. Try Acura, see if it gets a bigger laugh. Don't say some guy, say Bob. Don't say pet, say hamster, or better yet Dwarf Hamster. Be specific. It's funnier.