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This episode is presented by Mercury, the banking platform that makes this show possible. I can’t imagine trying to run my business without them. Learn more at https://mercury.com Robert Mac is on the show today to teach us what he's learned from great comics like Jerry Seinfeld and Mitch Hedberg. Robert has been doing stand up for more than a decade, and I wanted to know what he's learned about how to be funny, how to tell a good story. 00:00:00 Introduction 00:02:03 The #1 rule of comedy 00:03:29 The incongruity technique 00:06:07 Changing scale and focus 00:06:36 Wordplay explained 00:09:53 Pattern recognition 00:12:13 Know your audience 00:14:59 Why winning isn't funny 00:17:48 Using misdirection 00:22:21 The bait and switch 00:24:51 How one word changes a joke 00:28:53 Why writing matters 00:31:28 Seinfeld's hidden technique 00:36:43 Misplaced focus 00:42:00 The rule of three 00:46:07 More wordplay 00:47:15 The power of short stories 00:52:46 The role of details and context 00:54:11 What it feels like to bomb 00:56:33 Robert's writing process 00:59:08 What comedy can't be taught *About the host* Hey! I’m David Perell and I’m a writer, teacher, and podcaster. I believe writing online is one of the biggest opportunities in the world today. For the first time in human history, everybody can freely share their ideas with a global audience. I seek to help as many people publish their writing online as possible. *Follow me* Apple: https://podcasts.apple.com/us/podcast/how-i-write/id1700171470 YouTube: https://www.youtube.com/@DavidPerellChannel Spotify: https://open.spotify.com/show/2DjMSboniFAeGA8v9NpoPv X: https://x.com/david_perell
Robert Mack joins the show to share comedic lessons drawn from iconic figures like Jerry Seinfeld and Mitch Hedberg, discussing the essence of humor and storytelling.
"Robert Mack is on the show today to teach us what he's learned from great comics like Jerry Seinfeld and Mitch Hedber. And I said, "Robert, you got to come on the show. You've been doing standup for m..."
A brief sponsorship segment highlights the benefits of using Mercury as a banking platform for managing business finances effortlessly.
"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 t..."
The discussion transitions to analyzing famous jokes starting with Mitch Hedberg, illustrating the principles of comedy and punchlines.
"All right, back to the episode. Uh, I want to start with a 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 um it's Mitch Hedber. >> I..."
Analyzing jokes reveals how brevity and a skewed perspective create humor, along with examples from Steven Wright's work.
"Well, the thing about that too is it's takes two sentences to do that. >> It takes two sentences. Yeah. It's not like a whole story that you >> No, you don't need you don't need a background. You don'..."
The conversation focuses on the unique delivery and absurdity of Steven Wright's comedy, showcasing his distinctive jokes.
"His vibe, he's this shaggy guy. Um he gets introduced. He's like, "Ladies and gentlemen, Stephen, right?" And you're expecting this guy to run out on stage and he slumps along and uh you know uh nothi..."
Delving into the psychological triggers of laughter, the segment explains how incongruities and surprises elicit humor.
"Inongruity is probably the second most common trigger of laughter. It's when something doesn't fit. And when you lo like, I lost a button hole. That doesn't make sense. And when you realize, oh, I get..."
Exploring how jokes like Steven Wright's play with word definitions and absurdity to create humor.
"And that dissonance, having both ideas at once, the body reacted with a laugh. And they say that laughter comes from having these two inongruous thoughts at the same time and then realizing that every..."
Discussion reveals the inherent truths behind jokes and how irony plays a role in humor.
"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 a..."
The hosts discuss the anatomy of humor and how breaking down jokes can sometimes strip away their magic.
"Uh a minute ago I said I I am a big fan of science. I follow it religiously. Those are two thoughts that sometimes don't go together. And uh some people would call it irony when you have um fighting o..."
The conversation touches on jokes that contain contradictions, showcasing comedic wisdom and truth.
"This has a little bit of a that place is too crowded, nobody goes there anymore vibe. I said it the opposite. It is nobody goes there anymore, that place is too crowded. Exactly. Yogi Barra, >> right?..."
The segment discusses how exaggeration enhances the memorability of jokes, emphasizing the importance of vivid imagery.
"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 ..."
An intriguing discussion on how metaphors become impactful by being vivid and memorable rather than just being accurate.
"Well, you know, something about that one kind of works because vivid like vivid seems like it's important in hyperbole. If you can make a picture in someone's head that they're more more likely to rem..."
The comedians share self-deprecating humor as a means to connect with the audience, using clever examples.
"Right. Right. No, you're exactly right. There's so many jokes that people don't don't make it vivid. So, it's it it doesn't stay with them. But but I I have a joke about the truth. >> Bring it on. >> ..."
The discussion delves into how pattern recognition plays a vital role in how jokes are constructed and received by the audience.
"That's a name that's not like >> That's a real name. Uh it's a comedian who was very old when I was very young. And so I I don't know. Um he's like an old vaudeville guy. Um what I love about this is ..."
Highlighting the significance of audience connection, the hosts discuss how understanding audience patterns is key to effective humor.
"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 ..."
The hosts discuss the empathetic connection comedians have with their audience, enhancing their overall comedic effectiveness.
"Because our brains were so conditioned to think in certain ways that uh a good joke writer is able to manipulate how our brains work. and they set up a couple clues to go one way and then the punchlin..."
A humorous narrative about recognizing audience backgrounds illustrates how personal experiences shape comedic approaches.
"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 com comedians have such connections with their audience..."
Robert shares a humorous anecdote about the importance of understanding one's audience in crafting effective comedy.
"You don't have to prove yourself. You don't have to explain the background of this story. If once you're connected, you can take them you can take them anywhere. You reminded me of a of a funny story...."
The narrative continues as Robert humorously reflects on a failed joke due to assumptions about audience experience.
"And I have a joke about being um in Bryce Canyon in southern Utah. >> Love that place. >> It's beautiful. And if you don't know, it's these red sandstone arches and towers. It's where they film the Ro..."
Exploring the nuances of audience reception highlights the often unintended consequences of humor related to cultural background.
"When we were sharing some comedy quotes before this and one of the ones you sent me is that winning isn't funny. >> Charles Schultz >> winning isn't funny. >> Right. And that's that's totally Charlie ..."
The discussion continues, emphasizing the comedic appeal of underdog stories and relatable struggles.
"Um 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 a normal guy, an average guy. But his last special, he's talking about his kid..."
Discussing how relatable qualities in comedians foster quick connections with their audience leads to laughter and enjoyment.
"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 the..."
Exploring how acknowledging vulnerabilities creates immediate connections with audiences while enhancing humor.
"Like, I know I need to lay off the carbs. 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 str..."
Comedy is explored through visual cues, demonstrating how certain physical characteristics can enhance laugh potential.
"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 setu..."
Discussing the power of the rule of three in humor, the hosts illustrate how it can elevate a joke's effectiveness.
"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 cel..."
The conversation highlights how timing is crucial in comedy to elicit responses and create relatable humor.
"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 defe..."
The segment dives into the structure of jokes, highlighting misdirection as a key element to comedic success.
">> And why is this one funny to you? >> Well, it's got this misdirection, right? It's like uh first of all, the Bible pops up. So instantly people kind of tense up when they hear the Bible >> and tens..."
Exploring how the punchline's cleverness can guide audience realization and enhance humor through a structure of surprise.
"We have a curious setup. We have two different things. >> And then that means a book where the boy magician defeats the evil lord of the underworld. We're obviously talking about Harry Potter, >> of c..."
The hosts analyze the bait-and-switch technique in joke construction, emphasizing the importance of subverting expectations.
"You could see that. >> Exactly. Sold better than Harry Potter. Wait, what? Surprise. The jig makes it funny. >> Yes. And we call this particular type. I call it I mean there are a million different pe..."
The breakdown of a well-crafted joke showcases nuances in wording that contribute significantly to its humor.
"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, ..."
The segment emphasizes the importance of writing structure in jokes that allows audiences to engage and interact with humor.
"That one's great. Steve Hosteder is a is a very uh famous guy uh is a great jokemith and um >> a jokeith What is a jokemith relative to other kinds of comedians? >> Um really crafts a good joke. Some ..."
The hosts explore how changing specific wording could undermine the effectiveness and humor of a carefully crafted joke.
"What are what are the smallest tweaks that you could make to where the joke just doesn't work now? >> Well, I mean, it's obvious that um he's talking about in the second part, he's talking about the B..."
A brief segment introducing Base Camp as a tool for managing writing projects and deadlines effectively.
"So the um he's he's worded it in such a way that it can only be this. And so it'd be very easy to to switch it. If he changed Harry Potter to the the Bible at the end, that wouldn't be a surprise beca..."
The sponsorship segment explains how Base Camp helps organize tasks and enhance productivity for creative projects.
"Base Camp is a project management tool and it's different from the other ones which are loud and noisy and cluttered. They have feature bloat. Base Camp says, "No, no, no, no, no. We're going to keep ..."
Robert shares a humorous personal joke to illustrate the mechanics of surprise and comedic timing.
"And I had the founder of Base Camp, Jason Freed, he came on the show and I noticed that he really cares about writing. He cares about manifestos. He cares about great copy. He cares about telling a gr..."
The conversation shifts back to humor, discussing a joke involving a bait-and-switch that plays on audience expectations.
"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 uh t..."
Examining the reaction to a potentially risqué joke in a conservative setting emphasizes the delicate nature of comedic timing.
"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 be..."
The narrative reflects on how building tension through surprise elements in comedy can heighten audience laughter.
"good joke is it releases this builtup tension and right >> I think Freud is the one who was one of the first to to discuss that. >> Well, let me read it. Let's just go through it. My favorite thing in..."
A discussion about word choice reveals its impact on humor and audience perception, enhancing comedic delivery.
"What was so bad? What were you guys freaking out about? >> Yes. It's like the monster at the end of the book. It was me the whole time. >> Exactly. >> Now, if you were to talk about changing one word,..."
The hosts analyze how context can change the delivery and reception of jokes, highlighting the need for humor to be relevant.
"Too serious. There's no there's none of the roleplaying. >> Yeah. >> And so, I had to pick a word that implied both uh dressing up for a bedroom activity and dressing up for work. and outfit was the o..."
Imagery of unexpected twists in wedding speeches reveals the nuances of comedic timing and context within celebratory settings.
"So I want to show you this from uh from a wedding speech. Okay. So here we go. So husband here and then wife to his right. >> Last thing I'm going to say is that uh we're expecting >> everyone here to..."
Timing in comedy is discussed, illustrating how it can set up audience expectations for a punchline that turns on its head.
"His 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. Um but no the actual the truth of the mat..."
The humorous anecdote about celebrating a long marriage showcases the cleverness of self-deprecating jokes in capturing attention.
"You know what word just came to mind? plausible deniability. >> Mhm. >> 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 koshe..."
The conversation reflects on various approaches to humor, emphasizing timing's role in transitioning meanings and the portrayal of self in comedy.
"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 tha..."
A reflection on the impact of cultural context on comedy showcases how a joke can shift in effectiveness based on societal sensitivities.
"And I was also thinking of I watched this uh it was this speech one time >> and this was 50th anniversary of marriage and once again context right context. So, night of celebration. I love I love my w..."
The segment emphasizes how self-deprecating humor and honesty in relationships enhance comedic connection.
"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 bes..."
The hosts discuss how self-deprecating humor resonates strongly with audiences, as it fosters a shared sense of relatability.
"It's called the laugh of uh the laugh of victory if you're familiar with the Simpsons. >> Yeah. >> Nelson laughing down at others. >> Punching down. It's it's not in favor these days as much. But maki..."
The segment blends insights into the dual nature of jokes, appreciating wisdom behind humorous contradictions and truths.
"We had 40 We had three bad years, but 47 great ones. So, come on, folks. >> It's funny. It's kind of mean and it's kind of sweet at the same time. >> That's comedy. Sometimes it is a little mean. John..."
The hosts describe how effective joke writing enhances humor, enabling audiences to discover the punchline naturally.
"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 cr..."
The mechanics of effective writing promote audience engagement, allowing for deeper connections through humor.
"And uh if you've ever seen the seals, they're the cute ones. Um, this guy uh is a great he's also a jokemith. Writes these great oneliners. Used to write for Conan O'Brien. The point is if you write w..."
The conversation explores how playful themes reoriented around childhood can foster a humorous environment.
"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 a..."
The hosts dig into Seinfeld's observational comedy around everyday annoyances and the humor found in relatability.
"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 ..."
Analyzing how playful themes coexist with discreet humor to enhance relatability and connection within comedic storytelling.
"Yes. And there's like a seriousness about like I could die if I have bad milk. >> Bad milk, right? There's there's that. The thing about animal crackers though is the without if it was a different typ..."
The discussion shifts to Seinfeld's humor, analyzing how routine complaints become comedic insights through observation.
"That's why sex jokes work and fart jokes work and bathroom jokes work because there's something taboo almost about that or or sickening or gross. >> Okay, let's talk about Seinfeld. >> Sure. So, um, I..."
Investigating the comedic effectiveness achieved through exaggeration, particularly in Seinfeld's style.
"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 that that move Larry David has done 150 t..."
The complexity of observational humor is highlighted as the hosts share classic scenes from Seinfeld that epitomize awkwardness.
">> She wants to say hi. She's with her new boyfriend. >> What's he like? >> He's nice. Bit of a close talker. >> A what? >> You'll see. This is Aaron. Hello, Aaron. >> Hello, Aaron. >> So, how long ar..."
Seinfeld's humor is analyzed through the lens of awkward interactions, showcasing how the discomfort creates laughter.
"How'd you like a behind-the-scenes tour? >> Really, you could do that? >> Easily. >> It wouldn't be any trouble? >> Of course not. >> Where could we go? >> HOW ABOUT RIGHT NOW? I'M READY. How about yo..."
Unearthing humor in mundane scenarios is explored as the hosts reflect on the engaging nature of Seinfeld's material.
"Yeah. >> But but though that is exactly what what that show is about. It's about nothing and making it big. And you said you said exaggeration and and hyperbole, and that's exactly what it is. It gets..."
The segment explores how Seinfeld identifies universal experiences, enhancing relatability and connection to his audience.
"Everybody goes, "Oh, I know somebody like that." Which [laughter] >> cut to Jerry wearing a pirate shirt. Uh because he agreed to wear the pirate shirt. But um one of uh again one of the the goals of ..."
Deepening the understanding of observational humor, the hosts explore how relatable content resonates with the audience.
"Exactly. And uh 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 irr..."
The hosts analyze how relatable irritations encourage audience connections, enhancing the comedic experience.
"and then you're just way more irritable than the average person. But then you kind of play with that and then that leads to the joke cuz it is like universally funny when someone's like, "Hey, you kno..."
Sensitive observation fuels comedy, distinguished by the ability to amplify annoyances into a humorous experience.
"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 uh proc..."
Discussing the titans of comedy, the hosts analyze their observational talent and how that impacts their humor writing.
"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 tw..."
Exploring the segments on the close talker showcases how specific quirks become touchpoints for comedic relatability.
"You notice it, you exaggerate it, you represent it to the audience in a way that makes it entertaining. >> Yeah. And uh a bit of a close talker, huh? You're like, "Wait, I know what that is, but I'm n..."
Examining the close talker reveals the subtleties of presentation and recognition in humor that strengthens audience connection.
">> and uh then it comes to life, >> right? >> And then also like a good >> No, it comes to life is exactly it. You say something and now we demonstrate it. Here's the theory. Here's the proof. >> Yeah..."
The conversation wraps up by summarizing elements of memorable comedy where understanding and exaggeration play key roles.
"How can you not? >> Yeah. >> He's demonstrated it and 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."
The discussion begins about breaking conventional molds in performance and storytelling.
"And yeah, usually the third one does break things. um break the mold of the first two. The first two were what? Physical trips or something. What was the >> It was uh running a marathon. >> Running a ..."
An exploration of how comedy finds universal truths through different perspectives, including personal anecdotes.
"Well, it works in writing too, right? wouldn't work to say the pursuit of happiness, life, and liberty. It has to be life, liberty, and the pursuit of happiness. >> Yeah. The third one is has to be a ..."
A focus on the significance of storytelling in comedy and effective narrative structures.
"Yeah, that one. You don't need more. And it 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..."
Insights into what makes effective storytelling in comedy, including character and detail.
"If he did it as himself, if you're the bad guy, >> people might 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 puppet guy >> Ye..."
A discussion about the balance of details in storytelling and what truly matters in delivering a joke.
"And I'm always like, you just don't need all this setup. Like you could have 10% and it' be fine, but you need buy in >> when you're telling a story. Like you can sort of tell when you're telling a st..."
Exploring storytelling through anecdotes and the importance of stripping unnecessary details.
"I know another guy who is a a horrible storyteller and he had a great story. He 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..."
This segment contrasts storytelling styles and the importance of detail within comedic narratives.
">> My family had holiday celebrations and I was just interested in watching them tell stories and I would notice there was a distinct difference between my aunts and my uncles. My aunts would get caug..."
A conversation about the significance of details that enhance stories while also being careful not to detract from the humor.
">> Well, I would I would argue a little bit with that. >> Oh, tell me. Good. >> I would say good >> um if somebody said the year was 1945, blah blah blah, the kid was born. But the ants are the year w..."
Discussing various aspects of audience connection and factors that influence a performance's success.
"Um, show me what you got. >> It has some specifics. It requires some cultural knowledge as well. Um, pop culture stuff. The notorious B.I. once wrote a song where he predicted his own death. Do you un..."
Sharing personal experiences and feelings about failing to make an audience laugh.
"Or maybe earlier in the set you could talk about, you guys know Notorious B.I. is also known as Biggie Smalls and kind of plant that seed so the information is in the audience's head so that later whe..."
Discussing a personal experience of bombing on stage and the emotional impact of a failed performance.
"It's 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...."
Exploring the dynamics of audience engagement and the factors affecting the comedian's connection with the crowd.
"I just wanted to to nose dive out of there >> bombing bombing is brutal and sadly um for me and I'm sure it's the same for many performers the last show you have in your head is the one that you remem..."
Investigating the balance between audience dynamics and personal accountability for a performing comedian.
"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 it, it might be it might be on them. But there are so many things that..."
Exploring the process behind creating jokes and the evolution of comedic material.
"And um 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? And then walk me through you kind of ha..."
Insider perspective on the various methods comedians utilize to transform observations into comedic material.
"Um, sometimes I'm just walking down the street and there's a a sign or I see a guy or I see a dog who's wearing a a prettier sweater than the person who's walking the dog and I see there's something o..."
Delving into the creative process of joke writing and the insights gained during brainstorming sessions.
"So, I look at my notes and I see, oh, there's a dog wearing a sweater, and I just I free I freewrite whatever comes to my mind, everything about dogs and sweaters. And and sometimes things connect and..."
Conceptualizing the joke writing process as a collage of ideas and inspirations for humor.
"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. >..."
Exploring a humorous thought regarding dogs, internet culture, and potential comedic setups.
"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 h I'm glad I have a thumb. Dogs don't have a thumb. And then I got t..."
Insights into the curriculum and core principles for teaching comedy to aspiring comedians.
"Last question. So you teach comedy and so as you sit down to sort of structure the curriculum and saying hey these are the things that I want to teach people about comedy like what are the core princi..."
Explaining various comedic filters and techniques that comedians use to enhance their material.
"And we've talked about some of those. Hyperbole, >> misdirection, >> misdirection, this misplaced focus, um taboo. Uh there's a guy I mentioned, his name is Scott Dickers. He's the one who founded The..."
The process comedians follow in observing, processing, and refining their material for performance.
"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..."
Discussing the importance of universal experiences and specific details to evoke humor.
"My my mother-in-law, she weighs 1,000 pounds. Um, she weighs as much as two 500 lb sofas. That's not funny. But if I if I found another way of saying it that was interesting or exciting or push some l..."
Reflections on the process of learning comedy and becoming a more effective performer.
"So, those are the things I would focus on and try to do that in in an hour or over a course of five weeks depending on how much time I have for the class. >> Hopefully, I'm a little bit funnier now. >..."
Discussing the significance of different perspectives in comedy and personal growth within the craft.
">> Yeah. >> 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 ..."