Trickster humor is all about finding contradictions that we&#39;ve stopped noticing and pointing them out. It is also about crossing boundaries that are normally left intact. The tone of voice and the posture are essential to the humor.
If there were an Olympics in martyrdom, my grandmother would have lost on purpose…

Traditional jokes with punch lines are the hardest to pull off

Communication

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<li>Create an overarching story that is different from what you’re apparently talking about. </li>
<li>Something important has to be at stake. </li>
<li>Its viewpoint has to run counter to the one held by those currently in power.</li>
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3 rules for making irony memorable

It also impresses with intelligence: 
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<li><ul>
<li>But don’t try too hard. Wit flows from passion for the subject.</li>
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<li>Wit is all about overturning expectations. The wit is in the surprise.</li>
<li>To be witty, take the subject, but not yourself, seriously. Wit begins with yourself, with self-deprecation.</li>
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Wit is the humor that creates charm

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Humor can be hazardous to the health of public speakers. Most speakers want to be funny, but you've got to do humor well, or it falls flat and that's worse than no humor at all. Here I provide a guide for avoiding the worst mistakes of traditional one-liners and cheap irony, replacing them instead with ironic and witty humor that works and wins audiences over to your side. And, if you insist on using one-liners, I show you how to 'sell' them successfully.
<h3>Traditional jokes with punch lines are the hardest to pull off</h3>
Let's start with an example of a funny speech by Emily Levine.
Emily Levine is a self-proclaimed trickster and a very funny person. She's Harvard-trained and still manages to be hilarious. Emily's humor is all about finding the contradictions in modern life that we've stopped noticing. Things like the following sign in a beauty salon: Ears pierced while you wait. 
Just imagine the alternative. I'll leave my ears hear until 5. I've got a couple of errands to run. But I'll be back to pick them up. What? I couldn't hear you.
Trickster humor is all about finding those sorts of contradictions and pointing them out. Also about crossing boundaries that are normally left intact. If there were an Olympics in martyrdom, my grandmother would have lost on purpose...
Check out Emily and learn from her. She's a comedian in the classic sense - she tells jokes. That's very hard to do. As you watch the talk, note how she 'sells' her jokes with her body. When she talks about not hanging up on telemarketers, because Emily Post says it&#352;s rude, she devises another strategy. After the telemarketer has delivered about half his pitch, she says, "I interrupted with, 'You sound really sexy'. He hung up on me!" She says the 'really sexy' line with a husky voice, and sells the punch line with a pelvic stance. The tone of voice and the posture are essential to the humor.
So, if you're determined to attempt traditional comedy in your speeches, then practice selling the jokes with your body language and voice. You're got to be 100 percent committed to the joke - body and all. And then you've got to have a back up plan for recovery. Study tapes of <a href="http://www.thedailyshow.com/">Jon Stewart</a>, or any other of the late night comedians - he is the master of what to do when the first joke goes flat. Often his comebacks and reactions are funnier than the original line.
Beyond that, look for the contradictions. That's where the humor is, and the punch lines. Traditional humor is all about setting up expectations and then violating them, crossing the boundaries of expectation. And finding connections where no one else sees them.
<h3>Irony is the humor of the era</h3>
If you don't want to risk throwing out punch lines, consider irony. At its worst, irony is a cheap, easy way to get a chuckle and avoid making a commitment. At its best, irony is a memorable way for the alienated to comment on the 'in crowd', the powerless to bring down the powerful, and the hip to skewer the not-so-hip. John Hodgman provides a brilliant example of wonderful irony on TED.com. Check it out for how to do irony well.
Hodgman begins by talking about <a href="http://en.wikipedia.org/wiki/Enrico_Fermi">Enrico Fermi</a> the brilliant Italian physicist, and aliens. The kind that come in space ships and land in the Nevada desert, that is. Hodgman says, "Isn't it strange that he only asked for one thing? A gift of two healthy sperm whales? That's not true, but it is strange."
There are 3 rules for making irony memorable rather than cheap. Rule Number One. Create an overarching story that is different from what you're apparently talking about. This narrative misdirection enables you to take an ironical (because distant) stance toward your real topic. There's considerable wit in what Hodgman does, but the predominant mode is ironical. "The aliens might be very far away," he says, in explaining why we haven't seen them yet, "Even on other planets." He brilliantly illustrates the first rule of great irony by providing an overall narrative that is different from what he is apparently talking about. Hodgman's apparent narrative is all about his (non) encounters with aliens, but his real narrative is all about how he, a nerd, found love, got married, and remains in love today.
It's a very sweet story, told with delicacy and tact - and irony. Most cheap irony lacks the meta-narrative that gives a good story its structure. Cheap irony is usually just a pot shot at something the narrator doesn't like but can't do much about.
Rule Number Two. The second rule of great irony is that something important has to be at stake. In Hodgman's case, it's love. He is traveling in Portugal with the girl who becomes his wife, and she goes off on her own to check out a beach. She's a long time coming back to the hotel, and Hodgman realizes how alone he is in the universe. As he says, "I could not call her on a cell phone because the aliens had not given us that technology yet."
But what's at stake can be anything important that the speaker-narrator cares about. Cheap irony has nothing behind it - no alternative that it is proposing. Powerful irony points to a better way.
Rule Number Three. The third rule of irony is that its viewpoint has to run counter to the one held by those currently in power. Again, in Hodgman's case, the predominant viewpoint is that nerds can't find love. After all, it's the Prom Kings and Queens that get love, right? Hodgman quietly and ironically insists on the contrary, that nerds can find love, too. "Even though we are married, I love her and wait for her still,&#176; he says, perhaps the best last (ironical) line of a love story in recent years.
<h3>Wit is the humor that creates charm and impresses with intelligence</h3>
I have three suggestions for how you can achieve wit, but first begin by watching J. J. Abrams, the TV and movie producer and director of hits like MI-3, Lost, and the new Star Trek. The talk is witty, as is the man. This TED.com talk is also full of insights into creativity that will stick with you once the wit has worked its charm and moved on. 
First Suggestion: Don't try too hard. Wit flows from passion for the subject. If you feel strongly about something, you will find wit in the subject and you will share it with your audience. Unless of course you're a corporate accountant who's idea of fun is a late night with a multi-celled spreadsheet.
That said, one of the wittier speakers I've heard was a lecturer on accounting, who used the Wells Fargo company as his example, back in the day when it had to account for losses of the strong box because of marauding Indians. His passion for the subject of accounting led him to this witty way to explain an otherwise dreary subject.
Second Suggestion: Wit is all about upending expectations. The wit is in the surprise. J.J. shows a clip from the "Lost" pilot episode, with a downed aircraft and lots of gore and mayhem, with very impressive special effects. He says, "Ten years ago if we wanted to do that, we would have had to kill a stunt man... Take Two would have been a bitch." You're not quite sure where he's going, but the second sentence is witty because it is surprising.
Third Suggestion: To be witty, take the subject, but not yourself, seriously. Wit begins with yourself, with self-deprecation. It's one reason why the British are so much better at it, culturally speaking, than Americans. The British are expert self-deprecators, probably because they have to put up with more pomposity in the form of 2,000, rather than 200, years of tradition and history. But when pressed, we can do it too. J. J. Abrams says, of filming Mission Impossible III, that his favorite scene is the one that involves shooting a dangerous drug up Tom Cruise's nose. He says, "I quickly learned that there are three things you don't want to do. Number two is hurt Tom's nose." The scene, which you should now go back and watch again, actually has Tom Cruise's hand shooting the dart-filled gun up his own nose (because he knew how hard to push).
That's the magic of the movies. And that's wit.
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Humor can be hazardous to the health of public speakers. Most speakers want to be funny, but you've got to do humor well, or it falls flat and that's worse than no humor at all. Here I provide a guide for avoiding the worst mistakes of traditional one-liners and cheap irony, replacing them instead with ...