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Want to use humor to connect with your audience? How to write a joke with a great punchline? You will learn tips on how to talk funny and make people laugh.

Topics discussed:

  • Should you try to open the speech with a joke?
  • How to make people laugh in your speaking;
  • Want to write a joke? Learn two exercises;
  • How not to kill a joke.

00:00 Welcome to Steal The Show with Michael Port. I’m Michael and this episode is “How to Talk Funny”. It’s often recommended you open a speech with a joke, lie. That’s just generally not a great idea. Obviously, it’s great to get your audience laughing right off the bat, give people a genuine laugh and you put them at ease and make a quick connection. But you’re probably not a professional comedian, that’s not your job. So you tell a joke that doesn’t land, you can let the wind out of your sails pretty quickly. But, I can teach you how to use humor to make people laugh, to make them comfortable, to connect with you, and if you want to write a few jokes, I’ll show you how to do that too. And remember, this entire podcast is based on my book called, guess what? Yes, “Steal the Show.” Go check it out at Of course, you can get it in any bookstore, anywhere… I can’t say anywhere in the world because I don’t know if they have it in Zimbabwe yet, but I’m working on it, hoping to get there and I’m hoping you’ll buy it. And when you do, at, I’ll give you templates, free content creation templates, storytelling templates, tickets to live events around the country, videos and public speaking coaching and so much more. Basically, I’m just giving you everything I own. You want my couch; you can have my couch, just buy the book at

01:26 All right. Now listen, you wanna be funny, right? Let’s be honest, who wouldn’t wanna be funny? You wanna make people laugh. It’s a fantastic feeling to get them giggling, their face brightened up and their demeanor lightens up. Actually, I should do that as a rhyme that would be better; it gets funnier if I do it that way. So, their faces brighten up and their demeanor lightens up. Interestingly, I found that the biggest laughs that I get in a speech; they usually come from improvised moments not pre-written jokes. Although, those works as well if you know how to write a joke. And I’ll give you a little bit of insight or information on how to do that. I’m not a comedian. Please, don’t compare me to a comedian’s work like, “Wow! I saw Louis CK talking about how to write jokes and he’s much better than Michael.” Of course he was he’s a professional comedian. I’m just a guy who wrote, “Steal the Show” which is a very good book by the way.

02:14 All right, listen. Recently, I just delivered “Book Yourself Solid” as a keynote; I do them all the time. You wanna hire me? Please, feel free, call the office. But I gave this particular one to Transamerica. It’s one of the country’s largest financial services firms. Now, prior to my speech, there was a panel discussion on the compliance issues about texting with clients. Apparently, it’s a big no-no. So of course, what did I do? I open my speech by saying, “My advice to you, send text to your clients.” And I walked off stage. No. I actually spent about a minute or two off stage before I came back. Now, you’re listening to it now, maybe it’s not particularly funny. But in the moment it killed, it broke the tension that had build up in the room over this issue and the audience roared with laughter. It was a great way to start. Now of course, I hadn’t planned that. I just found the moment and I took it. So I took a risk, it might had fallen flat on my face but I took a risk and it seemed to work.

03:13 And by the way, I have fallen flat on my face many times, literally. I actually once fell off the stage into the orchestra pit. The best moment of the night. It was a big, big stage and really deep orchestra pit and I was right on the edge of the stage and I slipped and I fell, and you heard “Boom!” And I did what the kids do, I went, “I’m okay!” And the place roared with laughter, I jumped up, I was a little bit bruised but I acted cool like I was tough or something which I’m not really. And then I ran back up on stage and I kept going. And it was the best moment of the show.

03:45 So, if you wanna try your hand at preparing a joke in advance, or you just wanna learn how to find some humor, here are a number of insights that will help you. Now, a joke is often told in three acts. So you know how to tell a story, and I’ve done an episode on story-telling. Now, it may be in The Canon, you haven’t listened to it yet, so be on a look out for it, subscribe to this podcast and then you’ll get that particular episode, or maybe it’s already been released and you can go back and look through it. My suggestion, subscribe, write a review, say, “I love this guy. He’s really nice, he’s trying to help us be better performers, better speakers and I think with what I’m learning here, I can steal the show.” So a joke is often told in three acts. So if you know how to tell the story then you know how to tell a joke. And most jokes are told, like stories, they include exposition, conflict and resolution and suspense is the key. Remember though, the punchline is gotta be worth waiting for. If you build and build and build and build and build and build, then you hit the punchline, it works! But if it’s like, “blah, blah, blah, blah, blah, blah, blah, blah, punchline”, not funny. So it’s gotta build, it’s gotta build, you gotta build, you gotta build, you gotta build, you gotta build and then, “Bang!” you hit.

05:02 Now, some jokes are told by putting together the completely unexpected, as in what’s called the “two-story joke”. Story one, leads down one path. Story two, takes you down an alternate path that leads somewhere totally unexpected. Story one is the setup and story two is the punchline. So here’s a Mel Brooks’ joke. Story one: “Tragedy is when I cut my finger, comedy is when you fall on an open sewer and die.” And that’s story two because it goes in a completely different direction. So story one piques your interest because it’s an obvious setup, cutting one’s finger is not actually a tragedy and I guess, unless you cut off all your fingers, that would be a tragedy. But in this case, just cutting your finger is not actually a tragedy. So your audience tries to guess where you’re heading and then comes story two, the punchline with the twist where you give them something they don’t expect. It’s quite a delightful surprise. Even you falling in an open sewer and dying in this case is a delightful surprise.

06:02 You just need to make sure that they can predict where you’re going. If they can, the joke will fall flat. So here are two exercises that you can use to get started, trying to write a joke. Number one, you write a provocative or interesting story. Next, write down where your audience will think you’re heading. So what are their expectations? And then write story two and go in the complete opposite example. For example: A priest, a doctor, and a Rabbi walking to a bar. The bartender says, “What is this? Some kind of joke?” You see story one is a priest, a doctor, and a Rabbi walked in to a bar and the story two is the bartender says, “What is this some kind of joke?” So story one you’re expecting an actual joke because that’s the set up. Story two, is not a joke and then you can get a little laugh I’m not saying these jokes are great. I’m just giving you examples, come on.

06:56 Here’s the better one. Wendy Lehman, she wrote a joke. It goes like this, “The only way to really have safe sex is to abstain from drinking.” Now, story one is the only way to really have safe sex is to abstain. The last thing you’re expecting to come is from drinking and it’s very funny. So the punchline delivers something different than expected. It reveals a surprise. One of the things you can do that’s quite fun is to watch one of the late night programs, like a Jimmy Fallon, and watch him doing a monologue, and hit pause on your remote just before the punchline. Try to figure out, what do you think the punchline’s gonna be? Then you hit play to see what the punchline actually says. Next step, write a better punchline. [chuckle] Good luck with that.

07:44 So another component to humor is a shared social context that allows for instant recognition and then the setup is achieved. So, a lengthy explanation that would damage the joke or give a hint at the punchline is not needed. This explains why so many jokes have the same set up. Three men go into a pub, it’s instantly recognized as a joke. You go, “Oh, I know a joke is coming.” Good, I expect that. There’s a shared social context around it. One of the reasons humor doesn’t translate from sometimes from country to country, is because the shared social context isn’t there.

08:22 Now, as I mentioned earlier, I wanna mention it again because it’s paramount. You gotta make sure the punchline is worth the time they spent listening. So you craft a list of punchlines and then try them out with your friends, your family, your colleague. And again, these might just be for exercise so that you learn humor. You get a little more exposed to how you design jokes, how you tell stories that are funny because professional comedians, they test and they tweak their content for months or years before they bring it to Madison Square Garden. You may be at a comedy club in New York City and Jerry Seinfeld will walk in, get up on stage, pull out some yellow note pieces of paper from his pocket and tell some jokes. And the cool thing is that when you get really famous, your jokes are funnier. That’s all there is to it. You just expect they’re gonna be funny, so you laugh. That’s the way it works. So here’s my real secret, just get really famous and then your jokes get better. But in all seriousness, it’s in part because you’re given the timing.

09:21 So, if you’re at a table with say, six people and one them is Bill Clinton, Bill Clinton is gonna get the timing. He might take the timing because he’ll take the room. But all of our energy intention… Attention rather, is going towards him. And so he has the timing and timing rules in comedy. He, who controls the timing, controls the joke. I just made that up, that’s not some phrase in comedy. But I want you to recognize it. Whoever is the most powerful person at that table or the most important person at that table from a status perspective, that person generally is also the funniest. Even if they’re not considered very funny people because they have the timing.

10:07 Now, you can also use the Rule of Three as a joke structure. For example, same-same-different. Such as a t-shirt that says Paris, Tokyo, Fargo. Different, such as a t-shirt that says, “Paris, Tokyo, Fargo.” Get it? Paris and Tokyo are similar, cause they’re sophisticated cities, and Fargo, with all due respect, is not Paris or Tokyo. And by the way, if you have to explain a joke, it’s not particularly funny. You can also use the expected-expected-unexpected. She was pretty, she was shapely, she was a man. Now that is expected-expected-unexpected. That’s funny. Now professional comedians use the Rule of Three all the time. Here’s one from Chris Rock. I can’t do it like Chris Rock, but I will do my best. Chris Rock said, “There are only three things women need in life.” So he said, “There are only three things women need in life.” Notice how he’s already setting up the Rule of Three with saying there are three things women need in life: Water, food, and compliments. [chuckle] Which is not funny. It is very funny, but it’s completely sexist and inappropriate.

11:22 Now, Jon Stewart, he said, “I celebrated the Thanksgiving in an old-fashioned way. I invited everyone in my neighborhood to my house. We had an enormous feast. Then, I killed them all and took their land.” That’s funny. Now, there’s George Carlin, “One tequila, two tequila, three tequila, floor.” These are funny jokes and they’re all the Rule of Three. It’s very, very clever. And actually, they’re really quite simple. They’re not complicated jokes and they’re easy to understand and we often have a shared context. For example, at some point in our life, we may have had a few tequilas and wound up on the floor. That may have happened. And we all have had Thanksgiving together and we understand the story, the context around that particular joke. And we either are women or we know women. So, the Chris Rock one has some shared social context as well.

12:20 Now, the other thing that really helps when you are using humor in your story-telling, your speeches, et cetera, as in your life, is to laugh at yourself. When you joke at your own expense, you defy expectations. The audience expects you to play to them with authority but then you take them off guard when your punchline points at you. So, a friend of mine was a speech writer for a governor and became very unpopular which is not unusual for governors but he succeeded in rebuilding his support. Now, even so, a lot of the audiences were quite aware of his, let’s say, controversial record. And the governor would put them at ease with a couple of lines that always got a laugh. “It’s nice that people are waving at me with all five fingers now.” Like you would say “When I was a kid, my dad got me a summer job shoveling out the horse stables at the local track. I had no idea then, that it would be such a good apprenticeship for being governor.” So, he poked fun of himself.

13:18 One of the things that I do sometimes, not always but sometimes when I open a speech is, after my bio is read… Now obviously my bio, it’s got things like, “Michael Port is a New York Times best-selling author of six books, Wall Street Journal called him a marketing guru, Financial Times called him a sales guru, Boston Globe called him an uncommonly honest author”, and I could go on. The point is, it’s kind of a lot but the audience needs to hear that you know what they wanna know, so it’s important. And they might think, “Oh here comes this big shot, he’s gonna come on the stage.” So what I do is, “Hey, listen. Lean in, guys, I got a little secret for you.” And I actually ask them to lean in on the edge of their seats, so, “I ask you right now go ahead lean in.” Now, it’s very important that you make sure everybody does. So, if somebody doesn’t, you say “Yeah, even you too buddy, come on, you got it. There you go, big guy. Good”. Now everybody’s leaning in and say, “Listen, I just wanna tell you this quietly because there may be other authors in the room and I don’t want them to hear. How can you tell how much BS exists in any one particular field or industry?” And they wait, and they don’t know, and I stretch out the pause and I say, “Count the number of books written about it and I’ve written six. So, what does that tell you?”

14:38 And then I proceed to say “But look, here is the thing. My promise to you is I’ll keep as much of the BS and the fluff, and the hype, and all that stuff out of this presentation. I don’t think there’s any one way to do anything. So, I’m gonna give you one perspective, I’m gonna give you my particular perspective, it’s helped these number of people do x, y and z but there are lots of different ways to get to where you wanna go. So, you’ll resonate with et cetera, et cetera, you get the point.” So I’m playing, making fun of myself right off the bat and I kind of squash that like “Oh, here comes the big shot” concept. All right, now also, very important. You do not tell everyone how funny your joke is before you tell it. “Oh listen, listen, I gotta tell you a joke. This is hysterical. Oh my God! This is so funny. This is the funniest thing ever.” Okay, you killed the joke right there.

15:21 One time somebody introduced me when I was a guest on a podcast and they said, “Ladies and… This is Michael Port, one of the funniest guys you gonna meet.” And I got on the podcast. The first thing I said is “Dude, you can’t do that.” Now I will not tell one joke, I will not be funny at all because you can’t tell… You just can’t do that that just doesn’t work. You can’t set somebody up as being funny and you can’t set up a joke as being funny, or else the audience sits back and go “Oh, yeah? Prove it. Let’s see what you got kid.” Because the best jokes are often the ones that sneak up and just smack you in the face. Now, once you start don’t stop. Oh, my fianc√© said to me the same thing once, which is kind of interesting now that I think about it. Anyhow, moving on. So, commit to the joke or you won’t get a laugh. If you back off as you’re telling it or you tell it half-heartedly, the audience will feel your hesitation and assume the joke isn’t gonna be good. Also avoid detours. Jokes usually work best in its straight line, and don’t forget timing. I mentioned it before; I’m gonna say it again. It’s important to prepare and all the more important to execute.

16:30 Timing requires real awareness on your part. So, you need to make sure that you deliver the punchline at the optimal moment, and part of that is keeping an eye on the room and your audience who’s unsettled or restless. Do you have an interrupter in your midst? Which is different than an interpreter, by the way. An interrupter is somebody who interrupts you. An interpreter is someone who takes what you say and translates it into another language, hopefully, correctly. I’ve spoken in many different countries and I’m not sure that what the interpreter is actually saying is what I’m actually saying ’cause the jokes didn’t usually work when I went over there and I’m not gonna take… I’m not gonna take the blame for that. Anyhow, the point is, is that you should avoid detours because jokes usually work in a straight line. Did you see what I did? Did you see how… What I did is I took you on a detour? You are like, “What? What’s this guy talking about?” Stay in a straight line. Okay.

17:23 So, what you wanna do, if there’s a certain distraction in the room, or a lot of movement in one part of the audience, is to slow it down. You draw out the set up or the conflict, so the room is settled by the time you get to your punchline, so there’s nothing walking over your punchline, there’s no noise over your punchline. Now, create tension. Create tension. The optimal moment for the punchline is after you’ve built up tension with your set up. Take time. As I said, make them lean forward in their chairs, then when you deliver it, the tension will release with a bigger laugh.

18:01 And what happens just before the punchline? The pause, of course. For timing, the biggest weapon in your arsenal is the pause. Don’t rush it as you bring it home. And the moral of the story is wait, wait, wait and then land it. Also, a good joke gives the context quickly and effectively so the audience instantly recognizes the setup. If you take too long establishing the context, you’re gonna lose them. And then be appropriate; be very, very careful of offensive and off-color humor. I used a little bit in this one but I just walked up to that line. And if a few people thought “He went too far,” that’s okay; they should probably listen to a different podcast because I’m not going too far.

18:53 Each comedian and storyteller and speaker should decide what their line is and sometimes people want them to cross that line and other times they don’t. So, there are certain people you’re meant to serve and there’s others that you’re not. I just gotta comment on a comment card that was very strange. I was wearing a pair of Diesel jeans and on these Diesel jeans was this tiny little silver rivet right at the top of the fly area and one woman wrote on the comment form, “I thought his jeans were inappropriate because I couldn’t stop staring at the rivet right above his fly.” I didn’t even know what to make of that. I thought if she can’t stop staring at my crotch, there’s nothing I can do about this. I mean, come on, really? So I’ve gotten some chronic crazy comment cards in the past. So, be appropriate.

19:43 So look, here’s the thing, bad humor selects weak targets. Great humor at someone else’s expense should only take on the most powerful people in the room. See, that’s the power dynamic, at least to me, of good comedy. If you’re gonna make a joke at someone else’s expense, make a joke about someone who is in a higher position than most of the audience. You can make fun of the president or a well-known politico, as long as it’s not overly political or overtly political because that activates everybody’s baggage. Jimmy Fallon, he did a great job of this making hay, making so much fun of the buggy website for Obama Care but he never let his Obama joke get nasty or controversial. And a little joke focused on the CEO of the company where you’re speaking, that can put you in the side of the employees and in most cases, the boss will then take it just fine. Just be careful, do your homework in advance and see if the boss has a sense of humor or not, ’cause if they don’t, be careful.

20:45 Speaking of a CEO with a sense of humor, while doing advanced research to prepare for a corporate client, I discovered that two guys running the company made for a great visual contrast. The president was as bald as I am, while the CEO had a gorgeous mane of well-groomed black hair like I once did. Now, in doing my research, I checked around and not only did I hear that folks teased him about his manicured mane, but I made sure he’d be okay if I poked a little fun at it. And so the day of the speech arrived, a few weeks prior, I’ve been given a t-shirt that said, “With this body, who needs hair?’ I thought it was hysterical. So, I bought another one and I brought it with me. The first thing I did after I was introduced by the CEO with the great hair was to make a big deal about his absolutely extraordinarily shiny mane, how long it must take him to get it looking like that every day and how I’d kill for a head of hair like his. And then I asked the bald president to come up on stage, once I had him standing right next to me, I told him that guys like us have to stick together and I gave him the t-shirt.

21:55 Now here’s what I did, I notified the video crew ahead of time so they could get a close-up of the shot of the t-shirt because there were 2000 people in the space and there were six different TV screens, so without the video of the t-shirt on those TV screens, they would not be able to see it. So the video crew got a close-up of it right at my punchline and so it can be read on these six giant screens and it killed. Everybody loved it. Now, that’s an example of how you can get the audience on your side by needling the boss without going too far. Oh wait, one last thing before we wrap up, I almost forgot, a skeleton pulls up a bar stool and motions with a bony finger, “Bartender, give me a cold beer and a mop.” Now, that my friend, is a terrible joke.

22:44 If you wanna tell terrible jokes, go to, pick up a copy of “Steal the Show”. I will give you lots of bonuses, I’ll give you whatever I have. You want my couch, you can have it, you want my TV, you can have it, you want my wife, you can’t have her, that’s off-limits. But if you wanna learn how to steal the show, if you wanna learn how to do big things, if you wanna learn how to shine in the spotlight moments of your life, then “Steal the Show” is for you. I love you very much and in a very weird way. Keep thinking big about who you are and what you are for the world. This is Michael Port signing off. Bye for now.