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A
Robert Mack is on the show today to teach us what he's learned from great comics like Jerry Seinfeld and Mitch Hedberg. And I said, robert, you gotta come on the show. You've been doing stand up for more than a decade. And I want to know, what have you learned about how to be funny, about how to tell a good story. Let's have a conversation that's fun, that's high energy, that's obviously funny. And he goes, all right. The challenge is that dissecting jokes, breaking them down, is famously not a funny thing to do. So we said, okay, what are we going to do here? And we went out, we, we looked, we scavenged the Internet, and we said, let's go find our favorite jokes and our favorite one liners, and we'll go through them one by one. And as I do that, I'm going to teach you the rules, the principles of great comedy. You wouldn't believe it, but how I write costs a fortune to run, and it's thanks to Mercury, but I can even do it. They're the sponsor of this episode and a banking platform that I've been using for the past four years to run my own business. When I started How I Write, I expected finances to be an absolute nightmare. I got team members in four different countries. I had things to think about like currency exchange and taxes and expenses, and I was just dreading it. But honestly, banking has maybe been the easiest part. I can't remember running into a single problem, and it's because I've been using Mercury. I switched over from other, more traditional banks because Mercury is so well designed. It's easy to get started, it's easy to use while also feeling totally legit and secure. And Mercury gives me all the tools to run a global company like virtual cards, unlimited users, and the ability to customize each user's access level to exactly what they should see. And you know what, if anything goes wrong, if I have any sort of challenge, I can always talk to their support team, which is super responsive and actually helpful, which is pretty rare these days. And all that is why I can't imagine banking any other way. Mercury is a fintech company, not an fdic. Insured bank. Banking services provided by Choice Financial Group and Column NA Members. Fdic. All right, back to the episode.
B
I want to start with a joke by a comedian that I'm lucky to have met before he passed away. He's kind of famous. He's very famous. It's Mitch Hedberg.
A
I used to do drugs. I still do. But I used to, too.
B
Yes. And the reason this is funny is because comedy is all about showing things from a different perspective. That is exactly the number one rule of comedy is you get reality and look at it from a skewed point of view. And that skewed point of view has an element of surprise, and that is what's funny about it. So that joke is funny because his perspective is taking us from a completely different point of view. He's kind of. It's called a misplaced focus, and he's looking at things from a time perspective. I. I do drugs. I used to. I still do now. And it's basically your brain holding two different thoughts at the same time. And as you figure out the conundrum of both of those being true, your brain figures it out and you laugh.
A
Well, the thing about that, too, is it takes two sentences to do that.
B
It takes two sentences?
A
Yeah. It's not like a whole story.
B
No, you don't need. You don't need a background. You don't need a backstory. It's not one of those. You got to know my aunt before I tell you the story about my aunt. She's. No, it, It's. It's self contained, which is one of the. The beautiful things about Mitch Hedberg and Steven Wright. Oh, man, I just lost a buttonhole.
A
So this Stephen Wright.
B
This is Stephen Wright, who was the first real comedian I saw live performing. So I was raised on Steven Wright. Steve Martin. Martin. Monty Python. Monty Python I couldn't get my head around because it was so absurd and crazy. And Steven Wright is also absurd. And that is another way to.
A
What's his vibe? What does he look like?
B
His vibe? He's this shaggy guy. He gets introduced. He's like, ladies and gentlemen, Steven Wright. And you're expecting this guy to run out on stage and he slumps along and, you know, nothing fancy. He's not wearing a tuxedo, he's not wearing a jacket at all. It's just a guy in a crumpled shirt, and he kind of mumbles into the microphone, oh, man, I lost a buttonhole. He's just the exact opposite of what a lot of comedy at that time was, which is a guy in Vegas wearing a. Wearing a tuxedo, Right. And when you hear, when you hear the joke, he's saying something that we've heard before, kind of, oh, man, I lost a button. But his take on it is he's lost a buttonhole, which is sort of impossible. And it's one of these incongruities which is one of the surprise is the biggest, biggest trigger of laughter. Something that's surprising. And incongruity is probably the second most common trigger of laughter. It's when something doesn't fit and when you lose, like I lost a buttonhole, that doesn't make sense. And when you realize, oh, I get it now. He's conflating buttons and buttonholes. That is where the laughter comes from. They say, I'm a big fan of science, by the way. I follow it religiously. And they say that way back, the first laughter was based on animals fighting. This play fighting. And one part of the brain that recognizes fighting would be like, oh, no, we're in a fight. But. But another part of the brain that recognizes incongruity realized, oh, this is not a fight. We're just play fighting, practicing. And that dissonance, having both ideas at once, the body reacted with a laugh. And they say that laughter comes from having these two incongruous thoughts at the same time and then realizing that everything is okay. So biologically or evolutionarily, laughter was a sin that, hey, things are okay. No worries. And to this day, it's still a little bit like, if you can laugh at something, you have a little bit of control over it. It's not nearly as daunting. What do you got?
A
I got another Steven Wright one. Everywhere is within walking distance if you have the time.
B
Right. That's a perfect example of what he does. He's changing the scale again, like some of those first jokes, he's changing the scale. That misplaced focus. If. Yeah, if you have the time, you could walk anywhere. He has a lot of jokes about the planet. It's a. Yeah, it's a small planet after all. But I wouldn't want to paint it.
A
Right.
B
Right.
A
This is actually my favorite one. I went to a general store, but they wouldn't let me buy anything specific.
B
Well, this one has got more wordplay. He doesn't usually have a lot of wordplay, but general and specific are two different things that are. He's putting together. A minute ago, I said, I am a big fan of science. I follow it religiously. Those are two thoughts that sometimes don't go together. And some people would call it irony when you have fighting or competing ideas, general and specific. We should also point out to people watching that when you dissect a joke, sometimes it loses some of the magic, and we can get caught up in the details, but it's funny. And that's the bottom line, is it works. It Works. A lot of jokes work because a bunch of different principles are in play.
A
This has a little bit of that place is too crowded, nobody goes there anymore vibe. I said it the opposite. Yeah, it is. Nobody goes there anymore. That place is too crowded. Exactly. Yogi Berra.
B
Right?
A
This has that sort of vibe.
B
Anything that, that contradicts itself is funny because again, it's two opposing thoughts at the same time.
A
And there's kind of some wisdom about it there.
B
Yes, there's always a little bit of truth and wisdom behind a joke.
A
It is interesting that like there's an element of something is funny because it's true and if it's making people laugh, then there's something true about it.
B
Exactly. A lot of comedy legends, and I'm trying to remember the exact quote. Sid Caesar said that comedy is a kernel of truth that is built on. And somebody else said comedy is a fancy story with a little bit of truth at it at the end. There's always an element of truth that is the starting point and you zoom out or you tweak it, or you look at it from another point of view, or you exaggerate it, or you make it a character, or you make it absurd. And that truth is still part of it. And the change, the exploitation of it, the playing with it is what makes it memorable. Because if you said the grass or my mother in law's is large, there's nothing memorable about it. But if I say my mother in law weighs a thousand pounds, then you're able to picture it and remember it a little bit more. But there's always an element.
A
Right. My mother in law looks like the Michelin Man.
B
Right? Bingo. You get to see it in your head.
A
You're making something about that. One of works. Because vivid, like vivid seems like it's important in hyperbole.
B
If you can make a picture in someone's head, they're more. More likely to remember it.
A
Yeah. I was reading this book about writing one time and it was talking about metaphor and it was basically trying to make the point that a metaphor gets its potency as much if not more from being vivid as from being true. And you have to make a metaphor vivid, otherwise it just doesn't land right.
B
Right? No, you're exactly right. There's so many jokes that people don't. Don't make it vivid, so it's doesn't stay with them. But. But I have a joke about the truth.
A
Bring it on.
B
Bring it on. This is an older one. Red button said never raise your hands to your Kids, it leaves your groin unprotected.
A
Who is Red Button?
B
Red Buttons Name?
A
That's not like.
B
That's a real name. It's a comedian who was very old when I was very young, and so I. I don't know. He's like an old vaudeville guy. What I love about this is if you hear just the first part of the sentence, raising your hand. Never raise your hands to a kid. For me, I'm thinking, all right, this is going to be some statement about child safety or the importance of protecting the youth and nurturing them for the future, but there's a bit of a left turn, and it's about protecting your groin. And I. I've been. I teach comedy and I speak at conferences to companies about using humor in the workplace. And it does all these great things. And in the process of this, I've learned something called pattern recognition, which I think is the hidden secret of what comedy does and how comedy works. Because when I say, never raise your hands to your kids, your brain. Our brains are thinking of a certain thing. Oh, the kids, the future. You got to protect kids. Because that is the pattern that we're used to hearing. And patterns have helped us evolve and become the smartest creatures on the planet. So it leaves your groin unprotected is a left turn. It's a surprise. It gets the laugh. And here's how well our brains handle patterns. If I say Romeo, you think Juliet. If I say peanut butter, jelly. And so we got our cats, and we named them Peanut Butter and Juliet because they don't go together. But our brains were so conditioned to think in certain ways that a good joke writer is able to manipulate how our brains work. And they set up a couple. A couple clues to go one way, and then the punchline is something completely different because they know that our minds will follow certain patterns. It's the. It's the secret of comedy, is how powerful our brains are.
A
Well, the other thing, there's. There's a sense. I'm sorry, I hate this word, but it gets so overused. There is just a sense of empathy or. Or connection where what you're doing is you have to have a keen sense of where the mind of your audience member is, and you have to have a sense of where they're going now, what is the context, so that then you can shift it. And so I think part of the reason that comedians have such connections with their audiences and audiences with comedians in particular, is this sense of, wow, that person really gets me. Like, they understand where my mind is so well, that then they can make a joke out of it or something.
B
You're absolutely right. Have you taken a comedy class? Because that is like, rule number one is know your audience.
A
Yeah.
B
And if you know who they are, you'll know what the patterns that they're thinking are. And you're able to connect with them. And the minute you connect with them, you don't have to. That's half the battle. You don't have to prove yourself. You don't have to explain the background of this story. Once you're connected, you can take them. You can take them anywhere. You reminded me of a funny story.
A
Bring it up.
B
If I may, I was doing a show for a woman who was running for state lieutenant lieutenant governor of the state of Maryland. Okay. Who's an Indian American, and she had a fundraiser with a bunch of Indian businessmen to raise money. And I asked him, like, tell me about these businessmen. I want to know who they are, so I could write some jokes. And they're all college educated. They were all from India, but they live in the United States. They speak many languages, including English, which is important to me because I have a lot of wordplay in my act. And don't worry, they're smart guys. They'll get everything. And I have a joke about being in Bryce Canyon in southern Utah.
A
Love that place.
B
It's beautiful. And if you don't know, it's these red sandstone arches and towers. It's where they film the Roadrunner cartoons. Yeah.
A
Yeah.
B
Back when they filmed cartoons on location before all the animal rights protesters came in and shut down the Acme Rocket Skate Company once and for all. Anyway, I mentioned that, which always gets a laugh, but this audience, nothing because they weren't raised with that TV show. They didn't have that cartoon growing up. So a joke that always gets 100%. I got zero on it. Shook my confidence. And I had to kind of win them back because I didn't know that thing about the audience. So that pattern that I thought they would recognize, they did not, because it wasn't part of their upbringing.
A
We were sharing some comedy quotes before this, and one of the ones you sent me is that winning isn't funny.
B
Charles Schulz.
A
Winning isn't funny.
B
Right. And that's. That's totally Charlie Brown's story. If. If somebody won all the time, there's no conflict, there's no drama. There's nothing interesting about that. Carol Burnett's quote is great, too. Hers is comedy is tragedy plus time. There's always some Loss. There's always something about the underdog. Chris Rock had a recent special. He used to be the guy on stage who would talk about what it's like to be, you know, a normal guy, an average guy. But his last special, he's talking about his kids going to private school and living in this gated community, and he's not able to connect. And nobody's gonna connect with a multi millionaire who's famous around the world, but the lovable loser, Charlie Brown, the guy who's struggling to win all the time. That is somebody we can connect with.
A
Yeah, it's funny because you talk about winning isn't funny. And it's amazing how many comedians who instantly hit it off with an audience. I'm not saying they're the funniest ones, but I'm saying they're the ones that create the most connection in like 20 seconds. They have something about them. They're maybe a little overweight. They have a weird voice. They have a kind of a lame walk or something, and they know this about themselves. And then they sort of exaggerate it as they come up on stage. And then they just mention it right away, like, I know I need to lay off the carps. I know. And all of a sudden, everyone starts laughing. It's boom. Like, instant connection. Whereas a lot of times when I'll go to a comedy show, it's just struggling to connect with the person. It's too perfect, too refined.
B
The. I would say to your first point, if you can. If you can get a laugh, a joke is a. Is a setup. And then a punchline. If the setup is something that you don't have to say.
A
So true.
B
And you walk out on stage, that guy's seven feet tall. He has a joke about being seven feet tall. He doesn't have to say, hey, everybody in the audience who's looking at me? I'm. I'm a taller than the. He can automatically do the punchline because the setup is visual and is unspoken and the audience knows it before they. He's even taken the. The. The mic a hundred. So that is why sometimes people talk about their outfit. They talk about their hair, they talk about their looks. When I started, it was a common kind of trope. If somebody looked like a couple of celebrities. Oh, I know what you're all thinking. I look like so and so and so and so had a love child, right? And because you don't have to, you don't have to say, here's the backstory. The. The setup is. Is automatic yeah, let's do another one. This one's a long one. I read an article that said the Bible was the most bought and sold book last year. Harry Potter was number two. That means a book where a boy magician defeats the evil lord of the underworld sold better than Harry Potter. You're laughing a lot at that one.
A
Well, it's the same thing. I'm laughing for two reasons. One, I think the joke is funny. The other thing is I'm laughing because I now have X ray vision into the joke, into why it's funny.
B
And why is this one funny to you?
A
Well, it's got this misdirection, right? It's like, first of all, the Bible pops up. So instantly people kind of tense up when they hear the Bible.
B
And tension is a great way to build up a laugh.
A
Right. Harry Potter's number two. Okay, interesting. So it's like. Also, I'm kind of engaged, right?
B
I'm.
A
I'm excited to see where this is going.
B
We have a curious setup. We have two different things.
A
And then that means a book where the boy magician defeats the evil lord of the underworld, where unless obviously. Talk about Harry Potter, of course. Of course. Talk about Harry and Voldemort and all that. We got a scar on the forehead.
B
You can see that.
A
Exactly. Sold better than Harry Potter. Wait, what? Surprise. The jig makes it funny.
B
Yes. And we call this particular type. I call it. And there are a million different people who have a million different terms for kinds of jokes. I would call this a bait and switch, because you're offering two things. You're talking about one, but actually you end up you're talking about the other. Oh, he's talking about the Bible. No, he's talking about Harry Potter. And we switch them. So when you have two very specific things you're talking about and you imply that you're talking about one, you leave clues that makes it seem like you're talking about one, but you're actually talking about the other one. And that switch leads to a surprise, leads to a laugh, leads to this chemical dopamine that gets released in your brain and you laugh. And laughter is contagious. And all of these things creates. Create comedy. That one's great. Steve Hofstadter is a. Is a very famous guy, is a great jokesmith and a jokesmith.
A
What is a jokesmith relative to other kinds of comedians?
B
Really crafts a good joke. Some comics are physical. Some tell stories. He's able to craft things and focus on the writing rather than the performance or the character or the outfit?
A
Yeah. How would you. This sort of a strange question to ask, but how would you rewrite this in order to, like, not make it funny anymore? Right. Like, this works. What are. What are the smallest tweaks that you could make to where the joke just doesn't work now?
B
Well, I mean, it's obvious that he's talking about in the second part. He's talking about the Bible, and he wants us to think Harry Potter so he could say Harry Potter was a number two book. The Bible is a book where a boy magician defeats the evil lord of the underworld. But then he's revealing, he's playing his card, and then it's not funny. So the. He's worded it in such a way that it can only be this. And so it'd be very easy to switch it. If he changed Harry Potter to the Bible at the end, that wouldn't be a surprise because. Yeah, I know. You've been talking about Harry Potter and now you're talking about the Bible. It's just a perfectly crafted joke. It's rock solid.
A
Okay, so we're talking about how do you get your writing done and if you're thinking about work and how you can be more productive there. Well, I recommend a tool called Basecamp. Basecamp is a project management tool. And it's different from the other ones, which are loud and noisy and cluttered. Their feature bloat. Basecamp says, no, no, no, no, no. We're going to keep things simple so that you can focus on what actually matters, which is just getting the work done, you know? Now, for us, Basecamp is a place where we can track what we're doing with how I write, when episodes are being recorded, where we're recording them, the publishing day, all those sorts of things in one place for our entire team to look at. And I had the founder of Basecamp, Jason Fried, he came on the show, and I noticed that he really cares about writing. He cares about manifesting, he cares about great copy, he cares about telling a great story. And him and his co founder, they've written five books, and I can tell you that they bring the same care and attention to detail to their books as they do their software. So if you're thinking about work and you're asking, hey, how can I be more productive? How can I make my team more cohesive? Well, then I recommend Basecamp. All right, back to the episode.
B
My favorite thing in the bedroom is when she puts on her nurse outfit and leaves for work without waking me up. It's a Kind of a bait and switch. You're thinking maybe one thing, but it turns out to be the other. I have to tell you, I told this joke once at a 75 year old's birthday party. He was retiring from the military. He was 75. His family is in the audience. They're well dressed. It's a very formal event, very conservative. Grandparents, kids. And I do a joke that mentions the bedroom and a nurse outfit and the tension rises a little bit. But it turns out it's not a role playing joke. It's a joke about my, my wife is a nurse. And the tension built. I do the punchline, everybody laughed. Because that isn't one of the other triggers of, of comedy. A good joke is it releases this built up tension.
A
Right.
B
I think Freud is the one who was one of the first to discuss that.
A
Well, let me read it. Let's just go through it. My favorite thing in the bedroom is when she puts on her nursed outfit. And you're like, okay, first of all, vivid, vivid. Yes, we know where it's going. Robert, you shouldn't be saying that.
B
There are kids here.
A
There's kids here. This is 75th birthday party. Very conservative room. What are you doing?
B
Yes, tension. Tension builds and leaves for work without waking me up.
A
What was so bad? What were you guys freaking out about?
B
Yes, it's like the monster at the end of the book. It was me the whole time.
A
Exactly.
B
Now if you were to talk about changing one word. If I said she puts on her nurse costume, then you would think, oh, this is a role playing thing.
A
It's Halloween.
B
It's. Or Halloween. And going, going to work doesn't make sense. So it wouldn't work if I said she puts on her nurse uniform.
A
Uniform. Too serious.
B
Too serious. There's no, there's none of the role playing. And so I had to pick a word that implied both dressing up for a bedroom activity and dressing up for work. And outfit was the one word that covered both of those. Because again, I. You're leaving tips or clues. Clues that go to one direction and the punchline leads to another.
A
So I want to show you this from, from a wedding speech. Okay, so here we go. So husband here and then wife to his right.
B
Last thing I'm going to say is that we're expecting everyone here to have a great time tonight. Classic. That couldn't be done better. We're expecting everyone here to have a great time tonight. One of the, one of the things you cannot teach in comedy is timing. It's something you Just have to learn. And the timing of that was perfect because what he says, we're expecting. Our pattern recognition tells us we're expecting to have a child. We just got married. But no, the actual. The truth of the matter, the truth that we're playing with is we're expecting us to have a good time. So he gave them enough time to think. Expecting to have a baby already.
A
You know what word just came to mind? Plausible deniability. You know what I mean? It's like, we're expecting all of you to have a great time tonight. Like, the transcript is totally kosher. I love it when my wife puts on her nurse outfit and leaves for work without waking me up. Like, if you just read the sentence, it's like, it's totally fine. But the way that you've meandered down
B
the path or the way you've paused to change the meaning for the audience. I knew a guy who was dating in San Francisco, was dating a fireman. And he said, I like how he puts out fires. And it was just putting out and putting out fires are two completely different things that on the page look the same, but you add a pause and it changes. It's all about. It's all about the timing, but also the writing. And I think good writing leads the audience to what you want them to think.
A
I was also thinking of. I watched this. It was the speech one time, and this was 50th anniversary of marriage. And once again, context, right? Context, context. So night of celebration. I love. I love my wife. And he gets up, 50th anniversary, says, I just want to thank my wife for 47 tremendous years. And everyone sort of looks around like, what do you mean? He goes, Three of them weren't so great, but 47 were fantastic. And I want to raise a toast to that. And something about that is just. Was just hilarious.
B
Yeah. Playing, playing. There's. There's so many different ways that. That. That people will laugh. And when you. When you're admitting in front of your loved ones that three of these years weren't the best, I mean, that's something humbling and self deprecating, which are also great tools for laughter. If you can laugh at yourself, you can laugh at others. Somebody had a similar joke about, I've got three great kids and one that's so. So it's just. Same idea as you're downplaying something. Laughing down at others is another laughter trigger. It's called the laugh of. The laugh of victory. If you're familiar with the Simpsons.
A
Yeah.
B
Nelson. Laughing down at others, punching down. It's not in favor these days as much. But making fun of yourself to allow other people to laugh at you is a great way to get an audience to laugh, because it's okay. You're showing that it's okay to laugh at us. We had 40. We had three bad years, but 47 great ones. So come on, folks, it's funny.
A
It's kind of mean and it's kind of sweet at the same time.
B
That's comedy. Sometimes it is a little mean. John Cleese has a quote. He said, there's always an element of meanness because you're making fun of something. Maybe not a person, maybe you're making fun of the truth or making fun of the situation. And to me, comedy is all about writing. For some people, it's performing. For me, it's about writing. Because if you write a joke well enough, the audience can get it in their head without you having to tell them what the punchline is. Like this one, I got a box of animal crackers that said, do not eat if seal is broken. I opened the box and sure enough. What are the next four words? The seal was broken. And if you've ever seen the seals, they're the cute ones. This guy is a great. He's also a jokesmith, writes these great one liners. Used to write for Conan o'. Brien. The point is, if you write well enough, then the audience gets the joke. And there's something about when the audience figures it out themselves, they're invested more in the show and they get to pat themselves on the back for. Oh, I got that joke.
A
Exactly.
B
I'm on the inside. I'm in the cool club. I'm not one of the people who didn't get the joke because there's always those on the outside who try to. I didn't get that. Explain that one to me. And when an audience, because of good writing, when an audience person gets to pat themselves on the back, they're more invested in the show because it's more about them.
A
Okay. Animal crackers. What I like about animal crackers is that it takes us back to something playful. And it seems to me like a lot of what you're doing as a comic is getting people into a state of mind where they can laugh. Like animal crackers, they've. They're expired or something. Whatever. There's something about that that's benign. Whereas, like, if you were to have milk, do not open if the sea, you know, if it's expired or something. All of a sudden that's kind of gross.
B
Yes.
A
And there's like a seriousness about like, I could die if I have bad milk.
B
Bad milk, Right. There's. There's that. The thing about animal crackers, though, is the without. If it was a different type of cracker or if it was milk, seal wouldn't have the two meanings. And the joke pivots on having two meanings of the seal, of the container and the seal, the animal. And that's why he picked animal crackers instead of graham crackers or something else like that. But yeah, if it was milk, there is something. There is something disgusting and vile about that, which is also another trigger. Something that's disgusting or taboo. That's why sex jokes work and fart jokes work and bathroom jokes work. Because there's something taboo almost about that. Or sickening or gross.
A
Okay, let's talk about Seinfeld.
B
Sure.
A
So I got a theory that I'm going to sort of preface this with which is that a lot of what makes Seinfeld and in particular Larry David funny because I love Larry David is you take a small inconvenience or something annoying that a lot of people have felt and what you're doing is you're exaggerating the thing, but then you're naming the thing. And so now the thing that we've thought about but never even thought to put into words now has a name and has become a thing. And then it gets exaggerated and, and that, that move Larry David has done 150 times. And it's a very effective mood move. So this is from. From Seinfeld, which he obviously worked on.
B
We adore.
A
Elaine. She wants to say hi. She's with her new boyfriend. What's he like?
B
He's nice.
A
Bit of a close talker. A what?
B
You'll see. This is Aaron.
A
Hello, Aaron.
B
Hello, Aaron. So how long are you folks in town?
A
Oh, who are you on more days?
B
Three more days and then we're off to Paris. I love France. I was just there last year. In fact, I still have an envelope full of French franks. I'll give them to you. You know, I have a friend who works at the Metropolitan Museum of Art. How'd you like a behind the scenes tour?
A
Really? You could do that?
B
Easily. It wouldn't be any trouble? Of course not. When could we go? How about right now? I'm ready. How about you, Jerry? I'm sorry? Examine the artwork up close. Maybe I'll try and catch up with you. Oh, you must be Kramer. I've heard about you. I love. I love how Jerry is the only one who doesn't kind of back away. He's just standing up to him. Yeah, but that is exactly what that show is about. It's about nothing and making it big. And you said exaggeration and hyperbole, and that's exactly what it is. It gets something universal. And that's another thing comedy does. It gets something universal and makes it big so that everyone can relate to it. And if you put a name on it, it's easier to relate to. There's also the. The quiet talker, the low talker, the low talker, the low talker. Everybody goes, oh, I know somebody like that. Cut to Jerry wearing a pirate shirt because he agreed to wear the pirate shirt. But one of. Again, one of the goals of comedy is to find something specific and make it universal so everyone can experience it. And that's what his career is based on, is finding those little things that we haven't identified. He recognizes it, makes it bigger, puts a name on it. So everybody goes, yeah, I know about the no tuck in the hotel bedroom. And I know about the low talker and the quiet talker. And he's got thousands of those Larry David does.
A
Exactly. And I think it was an interview that Seinfeld did with Howard Stern, I think. But he just talks about how a lot of good comedy just comes from being a bit irritable, kind of constantly irritable, and being sensitive to what kind of drives you insane. And then you're just way more irritable than the average person. But then you kind of play with that, you work with that, and then let that leads to the joke. Because it is, like, universally funny when someone's like, hey, you know this thing? It's kind of annoying when they do that. You're like, yeah, yeah, yeah.
B
It's the laugh of recognition. Something that you've experienced that I'm identifying. That's one of the laugh triggers, is recognizing something. If I said, who here remembers dial up modems? And people in the audience go, yeah, yeah, I remember that. They laugh. It's not funny. But that recognition starts the joke, starts the laugh process. And I would say one of the first skills a comedian has is their observers. And they take note of stuff and they write notes down. And if you're sensitive, you said sensitive. If you're a sensitive observer, you're maybe you get annoyed easily and you twist that truth that you've recognized and make it exaggerated. You somehow tweak it so other people can see the Humor in that. That's. These are all steps along the process of writing a joke. You notice it, you exaggerate it. You represent it to the audience in a way that makes it entertaining.
A
Yeah. And a bit of a close talker, huh? You're like, wait, I know what that is, but I'm not quite sure what that is. What's that? And then you just see over. Exactly. You'll see over, over. And then it comes to life.
B
Right.
A
And then also like a good.
B
No, it comes to life is exactly it. You say something, and now we demonstrate it. Here's the theory, here's the proof.
A
Yeah. And a good bit kind of lives with you because I. I know some close talkers, and every time I see them do it, I just think of the bit. I just think of the bit.
B
How can you not.
A
Yeah.
B
He's demonstrated it and identified it with the name. And so now that will always have that name because he was the first one to put a title to it.
A
Show me something.
B
Okay, what do we got now other than that, Mrs. Lincoln, how was the play?
A
Huh?
B
This one is. Nobody knows who came up with this. This is 100 years old. Or actually, I think this came out in the 50s. And we were talking before about how sometimes comedy is mean and cruel. And. And this demonstrates that. It also demonstrates this what the founder of the Onion magazine has identified these comedy filters, he calls them. And one of the filters is a misplaced focus. So Lincoln gets assassinated, but this person is focused on. You know what? Tell me. Yeah, yeah, yeah. But tell me about the play. So it's, again, about taking things out of what should be focused on and focusing more on. On this other thing. This also requires some background knowledge.
A
I was going to say I didn't get it at first.
B
Okay.
A
And then I realized that we were talking about Lincoln, John Wilkes Booth, the assassination. And then I. Then I went through my head of, wow, that is, like, wildly inappropriate.
B
Inappropriate.
A
Like, dude, I'd say that. But I had to do a lot of work here in order to get it. And then once I did the work and I filled in the gaps, it was like I was part of the joke. And I was like, okay, that's pretty funny. But I didn't get it immediately in writing it.
B
You want to make it as concise as possible.
A
Yeah.
B
Without having too much backstory. So, Mrs. Lincoln, I'm hoping there aren't very many Lincolns that we know of.
A
Right. Ms. Smith wouldn't work.
B
No, no. Or even Kenneth Kennedy would work, because that has a Cache right to it.
A
Other than that, Ms. Kennedy, how was the drive?
B
Yes. How's Dallas? I mean, other. Aside from that. I mean, did you get some sun? Same idea. And you nailed it. It requires a little bit of historic knowledge or cultural background, which is another way that you can get a laugh. If I were to do that joke to people who didn't know American history, that joke wouldn't work. Unless I said, by the way, we had a president, he was assassinated during a play. It cuts all the setup out. Right.
A
But if you're in England, maybe you could do that with Princess Diana.
B
Right, right. Because those people have that background. Know your audience here.
A
There's a great tunnel in England.
B
Yes, yes. Do we have any pictures of it? Any paparazzi?
A
She loved it so much that she decided to stay.
B
Oh, it's terrible. But yes, but it's same idea. It's. It requires a little bit of a background. And again, this requires you to know your audience. And what do they know? If you. I'm. I'm older than a lot of crowds that. Or other comedians that I work with. And sometimes the audience is much younger. And if I were to do a Princess D reference, they might not get it right. If I did an Eartha Kitt reference, they might not get that.
A
I don't even know who that is.
B
Eartha Kitt is in. She played the Catwoman back in the old. The old Batman TV show. If I did Ella Fitzgerald reference, that wouldn't work, but if I did Beyonce, it would. So you have to know, you know,
A
where your audience is, you know what's funny. And I don't know if this is a cultural thing or whatever, but the Lincoln joke, I think is funny. The Kennedy joke, I think is funny. But the Princess Diana joke, I'm like, I went too far when I did that. There's something about that was like, mean spirited. Whereas, like the first two, there's an element of cruelty, but it's benign. It kind of works. But then if you, I don't know, joke about this thing, maybe it's like too much, too soon.
B
Too recent.
A
Yeah, too recent. Maybe there's like a cond. I don't know. It's like, maybe it's not my people. So it feels like now that's not
B
okay because it's a different group and you're. You're being mean. Whereas before it's okay. It's one of us. Right. I can make. I can make polish jokes. Because I'm polishing. Yeah. That I can't make A Mexican joke, because now I'm talking about them. Maybe that's it there. You've. You've said benign a few times. And there are some theorists who say they've tried to. To quantify what makes a joke. Why do people laugh? Louis CK Said, you can't. There's no formula for jokes. But these guys claim that a joke is something that's funny, that crosses a line, but it turns out it's benign, so it. Nobody gets hurt. So, for example, somebody slips on a banana peel and they fall, and they get up and walk away. That's funny because people shouldn't slip on banana peels. And so it's okay if somebody slipped on a banana peel and fell and didn't get up and a pool of blood started to come out of their heart. That would not be funny. Unless you're a very jaded comedian, in which case it's very funny. But there is this line of, if it's benign, it's okay to laugh because again, laughter means things are okay. And maybe for you, that line is, the British can laugh about that, but I'm not part of that community, so I can't make fun of it. Yeah, maybe.
A
Did you get some sun? I think that's very funny.
B
Well, enough time has gone by. Here's another joke that requires us to know a little bit about what's going on in current events. P. Diddy, Harvey Weinstein, and Bill Cosby walk into a bar. Do not go to that bar. And the cool thing about this joke is I can update it all the time. Unfortunately, there's always somebody else new in the news. So I can get rid of Bill Cosby and put in Jeffrey Epstein. That's exactly what I was thinking about. There's always an update. And this joke does very well. And it's because it combines a couple of these different laugh triggers. There's the rule of three, which we haven't talked about, which I think people get. Things that are in threes are funny. Two isn't a pattern. One is not a pattern. Two might be a pattern. Three is definitely a pattern.
A
But with the other thing, with the rule of three is that the third one breaks the law. The first two, right?
B
It can, yeah. Sometimes just having three seems natural because we've established a pattern. And oftentimes the third one is completely off the rails. This one, it's just three that are all very similar. And the thing that makes them similar is kind of taboo and creates a lot of tension. But then the joke is a joke about Jokes. It kind of steps out. And that's another technique of humor. It's called meta jokes. Jokes about jokes. Jokes. So generally, three people walk into a bar. The bartender typically says something, but that joke says, don't even go to that bar. We're not even. It's. It's breaking the fourth wall to talk about a joke. I have. I have an old friend who I started with who. Who got out of comedy 30 years ago, but he had a joke where he said, I broke up with my girlfriend. And the audience would go, oh. And he's like, no, it's all right. I needed the material. Oh, right. So it's a joke about comedy itself. So sometimes your perspective is so far removed, you can have fun playing with the idea of jokes. And that one does that. And that one is also the rule of three. And that one creates a lot of tension. And it's a great way to start a show because people are engaged. They're like, where is this going? And I hope it's not going where I think it's going, and I get a big laugh and able to. To win them over and then take the show where I want to go
A
with the rule of three. I was talking about how the third one often breaks the pattern. So I found this little infographic. Running a marathon takes this amount of energy. Climbing Mount Everest takes this amount of energy getting under your desk to connect some cords in the back of a computer. Right. It's like hyperbole, which we've been talking about. It breaks the pattern of the first two, which we've been talking about. And once again, it's kind of. This is a very different kind of benign. But I think that often just speaking to the most mundane things and sort of showing the ridiculousness of them works really well.
B
Misplaced focus. If you were to show that and cover up one of the first two and only had two things, the second one being the plug, it wouldn't be as funny.
A
It wouldn't work.
B
Third builds a little bit of tension. We're going somewhere. And yeah, usually the third one does break things. Break the mold of the first two. The first two were physical trips or something. What was a.
A
It was running a marathon.
B
Running a marathon.
A
Well, it's the most. The two most extreme things. Like you run a marathon. Cheese. And then you climb Mount Everest. That's like, geez.
B
Stuff that needs. Yeah.
A
You know what could be bigger than that?
B
Trip to the moon.
A
Jumping from space.
B
Yes. No, it's the. I got the USB thing upside down.
A
Yeah. Well, it works in writing, too, right? It wouldn't work to say the pursuit of happiness, life and liberty. It has to be life, liberty in the pursuit of happiness.
B
Yeah. The third one is. Has to be a little bit different to stand out to pop, which is what comedy is. It's making one of them look at things from a different point of view. Let's see what we got left. I only have a few left. This is a comedian named Dan Gabriel. He says in Japanese, the word problem is the same as opportunity, which I think is great, because I'd much rather say I have a drinking opportunity. It's got some wordplay in there. But what I love about it is Dan is my friend and a funny guy, and the more you know him, the more his jokes work. As a comedian, I find I like comics better when I get to know them because I get to see the truth in their. In their stories and in their jokes. And again, comedy is about finding a universal thing. Drinking, making it specific and interesting and funny so that everybody can get it. So it's universal. It's individual and specific. I love wordplay, too. And this has got some. Some wordplay in it. Yeah, that one. You don't need more. And it doesn't. It ends right there. You can put it in other bits about drinking, or it can just stand alone by itself. One more. I have one more. Should we do it?
A
Let me show you one. Okay, let me show you one. So I like this little. This. This. This little story from Louis CK And I want to hear about stories, like short stories, setting the context fast. This one's 24 seconds, but I think it goes through the whole. A whole arc.
B
A good laugh in 24 seconds is good. Yeah. I remember I was in a taxi, I think, in New York, and it was. The driver was Muslim, and there was a woman crossing in front of us, and he honked her because she went after the light had turned, and she gave him the finger. And he said to me, do you know, in my country, if a woman show you this finger, I could get out, beat her to death.
A
And if I drive by here a week later, she'd still just be laying
B
there
A
like nobody would even.
B
That's horrible. It's horrible, but it's funny. Stories are great because sometimes punchlines don't land. But a story has an arc, and people are invested in the arc, and so they tend to work more because they've just. The nature of this story has a beginning, middle, and end. And the end is so funny. And he's Able to deliver it because he plays a character, if he did it as himself. If you're the bad guy, people may not like you, but if you put it in somebody else. I don't know if you've ever seen a ventriloquist, okay? The. The. The puppet guy is nice, and the puppet is the horrible one. So your anger isn't at the performer. It's at the little puppet or the character that you play. And when he does the voice, he just has to do it a little bit to show some separation. This isn't me. This is the driver. And he sets up the story perfectly. I was in New York. I was in a cab. The guy was from a different culture. And that's really all you need to set up a story. You don't need to know what he was wearing, where he was driving to what day of the week it was. A story is just the important things that happen.
A
You know, I have a. Put it like this. A dear friend who is a horrible storyteller, right?
B
Not you, but a friend of yours.
A
And it drives me nuts. And the reason why this person is such a bad storyteller shares the wrong details and gets caught up on the wrong details. And I'm always like, you just don't need all this setup. You could have 10% and it'd be fine. But you need buy in when you're telling a story. Like, you can sort of tell when you're telling a story. Like, once someone kind of like clicks in and you want to get there as fast as possible. And when a story is laborious, it's almost always that they're just sharing too many details and the wrong details, Right?
B
And, well, if there's too many details, if you don't need those, then you're the. The punchline or the. The important part of the story is lost. Because we have to. To wait through this. I lived in. In Hollywood a couple years, and I got to take a screenwriting class at UCLA in their writing program. I totally lucked out. One of the things I remember is the. The professor said a story isn't everything that happened. The story is only the important things that happen that keep the plot going. I don't need to know what the guy was wearing when he walked into the bar. I just know that guy walks into a bar. That's all you need. Makes the jokes more concise. I know another guy who is a horrible storyteller, and he had a great story. He drove Bob Dylan around in a limo for a day. But the way he tells the story is he delivers that part first, and then it's all this other unimportant information. I was temping for a guy at a chauffeur agency, and he called in sick that day. And all of a sudden we're getting down to why the guy was sick. He ate some bad shellfish at a. No, the important thing is you drove Bob Dylan around and he. He loses it because he got caught up in unnecessary details.
A
Let me show you this. So this is from podcast that I did with Mitch Albom. Do you know who that is? He wrote a book called Tuesdays with Maury. Yeah, yeah, yeah. And we were talking about. I said, how do you tell good stories and stuff like that? And the. The point that he made comes to detail. So check this out.
B
My family had holiday celebrations, and I was just interested in watching them tell stories. And I would notice there was a distinc. Distinct difference between my aunts and my uncles. My aunts would get caught on the details. Was it 1945? When was Manny born?
A
Was he born in 46?
B
And then the uncles would tell the war stories.
A
So there we were.
B
See, we were coming over the hill.
A
We heard the shots. Then I turned to the guy next to me, I said, they're shooting at us. And I'm saying, that's how you tell a story. Like, I love that point. It's just the core things.
B
Well, I would. I would argue a little bit with that.
A
Oh, tell me. Good.
B
I would say, good, good. If somebody said the year was 1945, blah, blah, blah, the kid was born. But the ants are the year was 1940, or was it 1946? They're interrupting themselves. Right. Details are important because they paint a picture. They paint the picture in the head. Yeah. And sometimes a joke starts with this nebulous setup, and the punchline is very specific. And the specifics of it are what is required to make it work. A war story he can get away with. He doesn't need the details because war
A
does a lot of the work for you.
B
Right. When you're saying on the battlefield and we're catching fire, people can visualize that. It doesn't matter what year or what month that was.
A
Show me what you got.
B
It has some specifics. It requires some cultural knowledge as well. Pop culture stuff. The Notorious B.I.G. once wrote a song where he predicted his own death. Do you understand what that means? Biggie Smalls was also a medium man.
A
That's good.
B
This is Mark Christopher, another friend of mine. It is a great Joke. If you know that Notorious B.I.G also goes by Biggie Smalls. And also, you have to know a medium is somebody who is a foreteller of the future. And some people don't get that. So that joke doesn't always land, and there's really no way to fix it without ruining the joke. Or maybe earlier in the set you could talk about. You guys know Notorious B.I.G. is also known as Biggie Smalls and kind of plant that seed. So the information is in the audience's head so that later when you get to hear it, makes sense. But it's the details that are funny in that joke. But again, if the audience doesn't know those details, they're not gonna. They're not gonna get it. Which is one of the downsides of comedy, is sometimes a joke will not land. I have hundreds of jokes posted, and somebody has always said, I didn't get this one. Explain this one. Why is that funny? And if you explain it, sometimes when you break it down, it's. It's not funny, which. Which we've demonstrated today.
A
What's it like to bomb?
B
What's it like to bomb? Yeah. There we were. It was 1945. Bombs were falling. It's the worst feeling. It's the worst feeling ever. It is giving your best material. And when a joke doesn't work, you start doing all of your stuff. The hits, the things that will work. And when those don't work, you just feel like that you don't exist. I was doing a show once at a resort. It was an MGM resort, and we were in a suite. It was 18 floors up, and you could look out the windows. There's beautiful views. And the audience were sitting on couches facing me. And I'm doing jokes that are bombing. And I couldn't even make eye contact. And so I was just looking out the windows the whole time thinking, do these windows open? Because I just wanted to leave. I just wanted to nosedive out of there. Bombing, bombing is brutal. And sadly for me, and I'm sure it's same for many performers, the last show you have in your head is the one that you remember. And if the last show you do is horrible, you can't. The only way to get rid of that stench is to perform another show.
A
Okay, how often, honestly, how often do you think it's the audience's fault versus your fault?
B
I have a good friend who used to say, it's always your fault if you're not doing your job. If you're not getting laughs, you're not doing your job. And it's up to you to do your job. And I agree with that in part. But if I'm doing the same jokes that have worked thousands of times before and they're not getting. Might be on them, but there are so many things that can interrupt that if, if, if they don't know there's a comedy show and it's a surprise. Like at this birthday party that I did, if there's a TV on in the background, if somebody else, if there's music playing, if there's some other distraction, if it's not my crowd and the one that I told you about, it wasn't my audience and they just didn't buy what I was selling and they were eating all the birthday food. And I would say it's half on me. I should, I should connect better. First thing to do is connect to that audience. But if I don't know them, how do I connect?
A
And then walk me through. You kind of have an epiphany for a joke, like, I don't know, maybe that could be funny. An observation, a story that pops into mind. Walk me through the different steps from that to, boom, I nailed it on stage. Ah.
B
Wow. Good question. How much, how much time do we have? Because there's a lot of different ways. Sometimes I'm just walking down the street and there's a sign, or I see a guy, or I see a dog who's wearing a prettier sweater than the person who's walking the dog, and I
A
see there's something odd, like an Hermes
B
scarf type situation, something odd or interesting. My brain just goes, there's something in there. And so I write it down or I dictate it into my phone, and then I sit down. I have a writing time every day. Most days. Some days, occasionally I will sit down and, and, and spend my time writing jokes. So I look at my notes and I see, oh, there's a dog wearing a sweater. And I just, I free, I free write whatever comes to my mind. Everything about dogs and sweaters and, and sometimes things connect and sometimes they don't. But for the most part, once I start writing, new ideas come and a joke comes out of that.
A
So you feel like it's kind of like making a collage with words.
B
It's making a collage. It's putting a bunch of ideas together and see which ones bounce off each other and which ones rub against each other. You wouldn't see somebody dressing up a cat. Cats don't.
A
That would actually be funny.
B
Yes.
A
At the same time, that is a funny premise.
B
Right? Right. I have something the other day that I thought was funny. Like I, I was. My, my normal pad did not work and so I had to use a different thing to scroll on my home computer.
A
Like a mouse?
B
Yeah, the, the other thing was out of battery and so I was using the scroller thing on the mouse, which required a thumb. And I'm like, ah, I'm glad I have a thumb. Dogs don't have a thumb. And then I got the idea of what if there was an Internet just for dogs? And that's the premise and I haven't filled it out. But what would be right, what would be those websites? What would be the cookies? What would be if, if there was an Internet just for dogs, would the porn sites just be, you know, other dogs or cats or. And so that's a note in a notebook that at some point I'm going to sit down and write out. But it just struck me as odd. So I scribbled down the idea and I have a notebook of ideas and when I have time, I flesh them out.
A
Last question. So you teach comedy. And so as you sit down to sort of structure the curriculum and say, hey, these are the things that I want to teach people about comedy. Like what are the core principles, the core beats that you try to share?
B
It changes a lot. But for the most part, I talk about how laughter evolved. I talk about the things that trigger laughter. And if you know those, then you can kind of fit and write to those things. And then I talk about these filters or techniques that you can add to an idea to make the jokes pop. And we've talked about some of those. Hyperbole, misdirection, misdirection, this misplaced focus, taboo. There's a guy I mentioned, his name is Scott Dickers, he's the one who founded the Onion. He says there are 11 of these. He calls them comedy filters. So I teach those and then I talk about the process of what comedians do. They observe something, they process it, they write it down, they rebuild it in a way that has an element of truth, but also an element that makes it interesting or exciting so that somebody else will find it enjoyable. If you were just to get the truth and rewrite it in another way that didn't change too much. My mother in law, she weighs a thousand pounds. She weighs as much as two 500 pound sofas. That's not funny. But if I found another way of saying it that was interesting or exciting or push some limits, then people could recognize some truth, but also realize that there's something interesting or fun or exciting or laughable about that observation. It's all about getting something universal. Make it specific so that it paints a picture in someone's mind. So those are the things I would focus on and try to do that in an hour or over a course of five weeks, depending on how much time I have for the class.
A
Hopefully, I'm a little bit funnier now.
B
Well, practice. Watch a lot of comedy, read a lot of comedy, and if something strikes you as funny, write it down and explore that and hit me up and we can bounce ideas. Okay. It's about a different perspective. So another set of eyeballs is very helpful when you're starting a comedy career because there's. You have blind spots, I have blind spots. Another point of view, another set of eyes give you insights of. Oh, I didn't think of it that way. Yeah.
A
You know, I was listening to. It was a pastor preach, actually, and he said, you know, if I'm not becoming more loving as I get older, I'm living my life wrong. If I'm not becoming more generous, more kind, I'm living my life wrong. And you know what? If I'm not becoming more funny as I get older, I'm living my life wrong. I was like, I agree with that.
B
Amen.
A
I agree with that.
B
Robert Mack, this is great.
A
Thank you.
B
Sure. You're welcome. Thanks for having me.
A
Of course, of course.
Episode Title: Robert Mac: How to Write Comically Well
Air Date: February 26, 2026
Guest: Comedian Robert Mac
This episode features celebrated stand-up comedian Robert Mac in an energetic exploration of what makes writing funny—deconstructing legendary one-liners, analyzing comedic structure, and offering practical insights for anyone looking to be funnier on the page or stage. Mac and Perell use classic jokes from icons like Mitch Hedberg, Steven Wright, and Seinfeld as case studies, dissect the underpinnings of humor, and discuss how great comics connect with their audiences through empathy, timing, and vivid storytelling.
Perspective & Surprise as Comedy's Cornerstone
Conciseness and Self-Containment
Surprise and Incongruity
Pattern Recognition and ‘Left Turns’
Audience Empathy and Connection
Truth as the Core of Humor
Vividness and Hyperbole
Bait and Switch / Misdirection
Releasing Tension
Timing
Rule of Three
Meta-Jokes and Self-Reference
Wordplay and Double Meanings
Self-Deprecation and the Underdog
Shared Recognition
Context-Sensitivity and Cultural Knowledge
Benign Violation Theory
Economy of Detail
Specifics vs. Universality
Observation and Idea Capture
Refining and Testing
Mac’s core teaching curriculum includes:
The episode is playful, insightful, and encouraging—just as much about the mechanics of making others laugh as about building empathy, observation skills, and the bravery to fail. Perell and Mac invite listeners to watch, read, and practice comedy regularly, underscoring the importance of perspective and connecting with others.
David Perell: “If I’m not becoming more funny as I get older, I’m living my life wrong.” (61:35)
Robert Mac: “Amen.” (61:54)
For anyone wanting to write funnier essays, craft stronger punchlines, or simply see their everyday life through a more comical lens, this episode is both a foundational master class and a genuinely funny listen.