So, you want people to laugh at you in the good way when you’re gamemastering (GMing) a role-playing game (RPG). Which is to say, you want people to laugh on purpose at what you’re saying and doing, instead of having them laugh because you’re messing things up at a level that people can’t quite manage to ‘overlook.’ But you’re worried, because everybody tells you that comedy is hard! …Well, yes, it is. But that’s just an excuse to not even try. So, here are some basic guidelines:
Most importantly: if you cannot be funny, try to be fun. Normally, people writing these things try to weasel out of it and say that “You just need to relax” and “Everybody can be funny” and a bunch of other things that add up to “If you fail at this, it’s your fault.” Well, let me just rip off the bandage: not everybody is a natural comedian. And not everybody is capable of being even a serviceable comedian. It’s like everything else: some people are funny all the time, some people can be competent at being funny with a little practice, and some people just will never, ever be funny at all.
But if you can’t be funny (which is a trait) you can still be fun to be around (which is a behavior). If you can’t manage to make people laugh, then concentrate on making them smile. Pay attention to your players, prepare for your games, don’t get huffy when they short-circuit your plots, and generally chill. Do that, and you’re cresting the GM curve right there.
Assuming that you do have the ability to be funny, the second thing is NO FEAR. If you want a table where everybody is laughing, then you have to be prepared to go to where the laughter takes you. Taking things to their logical conclusions — well, that’s half of comedy right there. Don’t be afraid of embarrassing yourself. Revel in the idea of embarrassing yourself. If you’re trying to keep hold of your dignity, you’re doing it wrong.
Related to this is The Rules are not your friend. A lot of comedy involves chaos, and rules are there to keep chaos under control. That’s fine. That’s perfectly fine. But that’s not what you want when you’re trying to be funny. Or when you’re trying to help your players be funny. What you want is a situation where the people at the table are feeding off of each other in order to come up with silly suggestions and bizarre possibilities: at times like that, the question is not “Do the rules allow that?” It’s “Wouldn’t that in fact be awesome?” Awesome is the goal.
And then there’s There Shalt Be No Consequences. For good or ill. If the players have to run around with live chickens strapped to their heads for one adventure, fine: never bring it up again. If they did it because they got +5 to their Seduction rolls in the prospect, also fine… but you should still never bring it up again. That might sound weird, but: one of the things about funny is that it’s best when it’s fresh. A joke retained because it is useful rapidly stops being a joke and becomes something that you have to do and God help you if you don’t. That’s a definite drag, man.
Moving on, Be the butt of the joke. Seriously, you should always make sure that it’s always the non-player characters (or the GM!) who are the targets of humor, UNLESS a player begs to be the target. Not ‘all right with it’ or ‘taking it in good humor:’ if you’re going to unload on a character, do it only after his player enthusiastically signs off on it. And be prepared to stop when the player has had enough. And, of course, make sure that the rest of the party doesn’t keep on with the joke anyway*.
Lastly: Don’t expect a laugh riot every game session. Improvisational comedy isn’t the easiest thing in the world to sustain; and while you can reasonably count on getting a steady supply of chuckles, expecting to earn the hysterical belly laughs and weeping gasps every adventure is a bit hubristic. Relax, and let the laughs fall where they may.
*It may happen that you will find that somebody who you play with has less of a sense of humor than he or she thought, particularly when it comes to their dignity. This is why you want to have your players voluntarily agree to be the target of humor; that way, if it turns out that there was a misstep, then it’s at least understood that there was no premeditated malice involved on anybody’s part. That should be enough for functional adults. …And you are playing with functional adults, right? I mean, this is 2016. The potential player pool has never been larger.