Funny material in a presentation is virtually fail-safe if it is personal, completely relevant to the topic at hand, and, if possible, self-deprecating.
I can’t prove it but I believe self-deprecating humor goes over well because it gets the audience on your side — feeling sympathy for you in the literal sense of the word. “Sympathy” means identification or being in sync with. Audiences not only feel sympathy with you but also identify with similar situations in their own life.
For example: Here is a fool-proof joke (it has a setup and a punchline) a former professor of mine used to open each semester’s new classes. I take this description from the my book Write Like a Pro:
One of my professors when I was an undergraduate taught a large lecture class and began by taking attendance and reading the names from a roster. Some of the names were challenging, and of course many names have varying pronunciations. He invariably butchered a couple of names and asked for the correct pronunciation.
After the third act of butchery he recalled how he began his career as a television announcer, and learned that a cardinal rule of saying an unfamiliar name on the air is to first make every effort to learn the correct pronunciation, but if you can’t, never hesitate before you pronounce it. If you hesitate, you’ll sound wrong, even if you are right.
He then recalled the time when, as a TV reporter, he had to fill in at the last minute when the sports announcer fell ill. He was required to read, with no time to check out the pronunciations, a list of current boxing champions. He did all right with names like “Larry Holmes” and “Marvin Hagler,” but when he got to lightweights, mostly international boxers with names like Sot Chitalada and Jorge Ahumada, he just barreled through and brazenly bluffed. He even added the lilt of a foreign inflection as he grew bolder.
He was pulling it off, but the camera crew dissolved into a fit of laughter when he announced a bantamweight champion as a “tough little scrapper” he phoneticized as TEET-lay Vah-CAHT-ed. He of course added a confident bit of Spanish inflection to the name, which of course was actually “Title Vacated.” (Here he wrote “Title Vacated” on the chalkboard.)
He used the joke at the beginning of every semester, and sometimes in public appearances where he had to meet and address people with unfamiliar names. The joke invariably worked, or at least never failed.
Even if it fizzled or most people don’t get it, the joke is a relevant part of the presentation and there is a reason for it to be there – unlike the awkward and all-too-common scenario where a novice speaker suddenly inserts an irrelevant story about a horse walking into a bar.*
The second reason this is never-fail joke is because the humor is about the teller, so there’s no reason for anyone to become indignant.
In sum: Keep humor somehow relevant to the topic at hand, make it slightly self-deprecating with yourself as the key player, and even if it doesn’t get much of a laugh you aren’t standing there squirming after a bad, out-of-place joke.
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*The bartender says, “Hey, pal, why the long face?” Sorry.
