Elements of Wit: Mastering the Art of Being Interesting

Elements of Wit: Mastering the Art of Being Interesting

by Benjamin Errett
Elements of Wit: Mastering the Art of Being Interesting

Elements of Wit: Mastering the Art of Being Interesting

by Benjamin Errett


    Qualifies for Free Shipping
    Check Availability at Nearby Stores

Related collections and offers


Got wit?

We’ve all been in that situation where we need to say something clever, but innocuous; smart enough to show some intelligence, without showing off; something funny, but not a joke. What we need in that moment is wit—that sparkling combination of charm, humor, confidence, and most of all, the right words at the right time.

Elements of Wit is an engaging book that brings together the greatest wits of our time, and previous ones from Oscar Wilde to Nora Ephron, Winston Churchill to Christopher Hitchens, Mae West to Louis CK, and many in between.

With chapters covering the essential ingredients of wit, this primer sheds light on how anyone—introverts, extroverts, wallflowers, and bon vivants—can find the right zinger, quip, parry, or retort…or at least be a little bit more interesting.

Product Details

ISBN-13: 9780399169106
Publisher: Penguin Publishing Group
Publication date: 10/07/2014
Pages: 256
Sales rank: 1,109,642
Product dimensions: 5.50(w) x 8.20(h) x 0.60(d)
Age Range: 18 Years

About the Author

Ben Errett is the managing editor for features at the National Post, a Canadian national newspaper. He lives in Toronto.

Read an Excerpt

*And P. G. Wodehouse, from whom this dedication is borrowed


Why Wit?

There you are, in a big sales meeting. The client makes a weak joke in your direction and the boss looks your way. Say something. Say anything. Well, not just anything—you need something clever but innocuous, smart enough to show your intelligence without showing off, something funny but not a joke. You don’t want to be offensive, snide or holier than thou. If this were a game of tennis, you’d simply want to keep the ball in play. At this moment, what you need is wit.

Unfortunately, in the time it took to read those sentences, your window of opportunity has slammed shut. The pregnant pause gave birth to awkward silence, and a colleague coughed, or spoke up, or dropped a pen. The spotlight has shifted, at least for now. But this will happen again, one day. A moment like this will be presented to you and you alone. You can once more hope for a distraction. (Or maybe hire your coughing colleague to follow you around, hacking you out of difficult situations.)

Alternately, you can respond with just the right words at just the right time, putting the client at ease, impressing the boss, brightening the room and showing yourself to be in command of the situation.

OK, so maybe you don’t attend sales meetings. You’re self-employed. You avoid people who cough. Still, wouldn’t you choose the second option? Of course you would. But how?

This book is how. It’s also why, and most important, it’s who.

What if one of the Great Wits had been sitting in your chair in that moment of need? Say Oscar Wilde, green carnation in lapel and all, was prepared to offer a rejoinder on your behalf. Why, it would be like when Alvy Singer enlisted Marshall McLuhan to quiet a loudmouth in Annie Hall.

To be clear, the physical reanimation of the illustrious dead is sadly not the subject of this book. Instead, it’s a deep dive into the character traits of the Great Wits, those names seen most often at the end of aphorisms and quips, with one express purpose: To find out how they did it. What skills, talents, flaws and peccadillos fixed their wit in the popular imagination? And—this is where you, sitting in your little sales meeting, praying for inspiration, come in—how can a modern reader learn from these individuals?

In some cases, the lessons are almost entirely what not to do. There are Great Wits who led horrid lives, the wisecracks coming at the price of just about everything else. Can you subtract the substance abuse, the cruelty, the thwarted aspirations and the abject misery to leave behind a facility for sparkling epigrams? This book says, you know what? Sure you can.

A Brief Socratic Dialogue That Includes Finger Foods

We open on the Author’s sitting room. You sit side by side in tastefully upholstered wingback chairs. The fireplace is crackling away and there is still frost on your respective martini glasses. The Reader is briefly surprised by the transportive power of words—a moment ago you were thumbing through this book on the new and noteworthy table at the bookseller, but maybe that’s the Tanqueray talking. You regain composure and repeat your question.

READER: What’s the point of wit?

AUTHOR: The sharp end, the part that hurts.

READER: You know what I mean. What’s it for?

AUTHOR: It’s for intelligent conversation, sharp thinking, laughter, truth and human civilization. But what’s more important is what it’s against.

READER: Which is?

AUTHOR: Regurgitated thought, talking points, doublespeak, stagnation and dullness.

READER: So it’s for good things and against bad things? These days, who isn’t?

AUTHOR: Ah, but wit is the horse that best pulls that crowded bandwagon.

READER: And you’re saying she’s been put out to pasture by mistake?

AUTHOR: Exactly. But not by mistake, really.

READER: So what do we need to bring her back, aside from another drink?

The Author swallows the last drops of his martini, fetches your empty glass, passes you a plate of deviled eggs and walks over to the well-stocked beverage cart.

READER: Less vermouth this time, please.

AUTHOR: Of course. Now what I mean to say is that wit hasn’t simply been gently forgotten. It’s been misunderstood, redefined and twisted into a meaningless word. Its definition is now barely defined.

READER: So who’s made wit so meaningless, what did it used to mean, where did we go wrong, when was this alleged golden age of wit and why should we care?

AUTHOR: You forgot how.

READER: How will you answer my previous questions?

AUTHOR: The insecure made it meaningless; it once meant good sense that sparkles; we killed it by accusing it of cruelty and memorizing bad jokes instead; it was ascendant during the Enlightenment, but perhaps also during the 1920s; and we should care because it’s the best possible use of our brains.

READER: The best possible use of our brains? What about curing diseases? Repartee isn’t much use against the Ebola virus.

AUTHOR: OK, “best” may be a subjective term there. But wit, if we return to its original definition—and perhaps dress it up a bit for the twenty-first century—can get us to all sorts of discoveries.

READER: And that original definition is good sense that sparkles?

AUTHOR: In brief, yes. That’s how the seventeenth-century French thinker Dominique Bouhours defined “bel esprit,” literally “beautiful spirit.” Or as thinkers like Johnson, Hazlitt and Coleridge defined it in England at about the same time, it’s the rapid combination of disparate ideas to create delight. Our definition is even simpler: Wit is spontaneous creativity.

The Reader helps self to a third martini and a fistful of gherkins.

READER: So you’re saying wit is creativity?

AUTHOR: Wit is the ability to be creative on the fly, to combine ideas in conversation, to make connections quickly and with joy, and in doing so make life worth living.

READER: Wit is necessary, sparkly, the opposite of jokes and similar to creativity? I can see why you say it’s misunderstood.

AUTHOR: The three-martini introduction probably isn’t helping. Shall we return to the book?

READER: (Hiccups and nods appreciatively.)

Defining Our Terms

Wit is, for our purposes, spontaneous creativity. Note that this definition doesn’t specify that wit is true, or that it’s funny. We might add the words “to create delight” on the end of that definition, but on some level all creativity is delightful to a thinking mind.

How did we get to this definition? As we’ve seen, there were some brilliant Enlightenment thinkers who set out inspiring meanings for the word “wit.” The problem is, they were too good. They made wit sound like the best thing ever, the ultimate compliment and the pinnacle of human achievement. Soon, that meant everything good was wit; any good idea, clever remark or clear thought. Wit, as C. S. Lewis writes in his essay on the word, “suffered the worst fate any word has to fear; it became the fashionable term of approval among critics.” This led to it being further twisted, its meanings conflated until it was “semantically null.” Now it has come to rest as a vague subset of humor, used to describe certain movies or books but rarely in any specific way.

That didn’t totally happen with the word “wit” when used to describe a person. If you refer to someone as a Wit, your meaning will generally be understood. Now, we arrive at the concept of creativity from the Enlightenment definitions of wit as an attribute, but we can also get there as we talk about the Wit as a person—though by a very different path.

There is a small body of research from the 1960s on the character of the Wit, much of it coming from a mysterious U.S. military research group known as Serendipity Associates. The U.S. Air Force, it seems, was very interested in harnessing the power of the Wit. It funded a series of papers by this group to examine who wits are and how they behave. In 1963’s “The Wit in Large and Small Established Groups,” the Air Force found that “deliberate wits are associated with higher morale and greater role clarity and efficiency in small groups.” A year later, in “The Wit and His Group,” a study of two six-person groups found that wits “expressed a positive self-image,” and that groups containing wits “evaluated the group experience favorably” and “did better on a problem-solving task than others.”

And in 1965’s “Wit, Creativity and Sarcasm,” researchers made the jump to creative thinking, finding that wit and creativity were positively correlated, and that while the Wit was not an effective leader in a group, having one around generally made everyone better at problem solving. With no real evidence to support this idea, I’d like to think that NASA used this research to choose the members of the Apollo missions, and that when the Navy assembles a team of SEALs for a perilous mission into enemy territory, it always includes at least one happy warrior. This would explain the presence of lovable doofus Chris Pratt in the otherwise lovable-doofus-free Zero Dark Thirty.

Further research solidified the link to creativity—it’s “the best single significant predictor of wit,” Dr. John F. Clabby wrote in 1980’s “The Wit: A Personality Analysis”—but from that point, the mention of wit in psychology research all but stops. At about the same time, there’s a marked increase in the study of creativity. Studies of how and why creativity happens were refined into concepts with names like divergent thinking (generating many different ideas) and conceptual blending (bringing those ideas together), both of which have a more than passing resemblance to the old “rapid combination of disparate ideas.”

The research interest in creativity intensifies after 1990, as that’s when U.S. student scores on the Torrance Tests of Creative Thinking stopped improving. In the field of IQ testing, there’s something called the Flynn Effect, in which average IQ scores creep up by about three points a decade. No one’s sure exactly why this happens, but the most interesting and broad explanations have to do with the effects of modern life on our minds: We have to be smarter just to work our smartphones.

The Torrance Tests had similar findings, but only until 1990. At that point, scores start decreasing; year after year, people actually become less creative. Why 1990? It’s unclear, and while it almost certainly has nothing to do with the fact that Dances with Wolves beat Goodfellas for the best picture Oscar that year, we will make a passing mention of that travesty anyway.

As of 2010, scores were still falling, hence a Newsweek cover story titled “The Creativity Crisis.” Why is this happening? The usual culprits of TV and video games are often blamed, as is the education system with its standardized tests. But as with the Flynn Effect, no one’s really sure. The one certainty about this news is that if you’re a social scientist looking to have your research funded, it can’t hurt to highlight the word “creativity,” and maybe throw in some neurobiology while you’re at it.

And therein lies the problem with talking about creativity: It’s a huge subject with many working theories and even more definitions. The act of creation is exactly what a sculptor does, for instance, but creative thinking is just as necessary for genetic researchers and CEOs.

A worthy parsing of what creativity means comes from Mihaly Csikszentmihalyi, a psychology professor who wrote a book called, creatively enough, Creativity. As he explains, there are “three different phenomena that can be legitimately called by this name.” In inverse order, he discusses people who’ve dramatically changed the culture, people who “experience the world in novel and original ways” and then the group we’re most interested in here:

The first usage, widespread in ordinary conversation, refers to persons who express unusual thoughts, who are interesting and stimulating—in short, to people who appear to be unusually bright. A brilliant conversationalist, a person with varied interests and a quick mind, may be called creative in this sense. Unless they also contribute something of permanent significance, I refer to people of this sort as brilliant rather than creative—and by and large I don’t say much about them in this book.

We’ll say plenty about them in this book, and the distinction Csikszentmihalyi makes is an important one. By his definition, some of the Wits we’ll meet are merely brilliant, some are creative and some are both. But what of those who may have created something of permanent significance but were much more dazzling in conversation? Or how about our contemporaries, those whose work can’t yet be tested for permanence because they’ve only just finished it? We’ll stick to creativity in our definition, and if this book helps you become spontaneously brilliant instead of spontaneously creative, we’ll assume you won’t demand your money back.

So think of wit as a backdoor into creativity, then. It’s not the sort that will help you create a Fortune 500 company, a poem that speaks to a generation or the next dance craze, at least not by itself. But it will help you make the most of daily conversations and interactions and feel more at home in the world. And who knows? That could be the first step toward something bigger.

A Question of Timing

But what about the spontaneity part of our definition?

Calling it spontaneous creativity would seem to put a premium on wit in conversation, since wit on the printed page is impossible to certify as impromptu. By spontaneity, we mean creativity that appears to happen at the speed of thought and in the moment. The key words here are “appears to happen.” Are stand-up comedians witty? The best are, sure, even though we know they’ve painstakingly honed their material. Wit can shine on the printed page, though even at this late stage in the history of books, it takes many months for them to pass from writer to reader. In a movie or television show, the wittiest dialogue may have been improvised—it’s a badge of honor for actors to ad-lib a great line—but it’s far more likely to have been scripted and rehearsed with great care. And even on talk-show interviews, we know the best quips have been drawn out of the guests in green-room interviews, with the hosts prompted to say, “So I hear you’re having trouble with your pet iguana” as though it’s a perfectly natural subject of conversation.

We should also note that wit need not even be in language: In art and especially graphic design, visual wit is among the highest of ideals. To borrow the title of an excellent book on the subject, wit in this context—as perhaps in all contexts—should create “a smile in the mind.” Take, for instance, the FedEx logo. Even if you’ve never used the courier, you can probably see its trademark font and colors in your mind’s eye. But did you ever notice the arrow hidden between the “E” and the “x”? This nearly subliminal message—a perfect symbol for its service—is famous in design circles for being hidden in plain sight. And indeed, your mind smiles when you see it. Unless you’re a graphic designer, though, this won’t directly help you master the art of being interesting, so in this book we’ll keep our focus on verbal wit.

The key in all of the above instances of wit is the perception of spontaneity, the impression that the lines were dashed off, not labored over. This definitely doesn’t mean they actually have to be spontaneous; in fact, we will see that most of the Great Wits were anything but. The great conversation retorts were very often rehearsed and regurgitated. This doesn’t make them sparkle any less brightly. On the contrary, it means that you and I have a chance at re-creating such verbal triumphs. Spontaneity is entirely in the ear of the beholder.

Our Elemental Breakdown

To explore wit by examining witty sayings is like studying a snowflake by putting it under the microscope. By the time you’re ready to look at the intricate structure in your well-heated lab, all you’ll see is a little puddle of water. Far better to examine the process by which snowflakes are made, which brings us to the elements of wit.

First, we examine where wit comes from. In order to amusingly combine concepts on the fly, you’re going to need some concepts. And so we begin with Hustle, meaning the way you’ll acquire these ideas. The word doesn’t generally refer to library research, and that’s why it fits: Most of the concepts the Wits used were absorbed from the popular culture of everyday life. There are books of quotations, newspaper columns, things hollered by angry spouses, movie lines and more. The best spontaneity, we shall see, is well practiced.

Then comes Flow, a somewhat magical concept that explains how you let your mind and mouth go. There’s a whole genre of art dedicated to this: Rap. How musical improvisation happens is key to the practice of wit.

Closely related is Intuition, which is basically a way to describe the thinking we do when we’re not thinking. It often seems that the best ideas bubble up from some hidden part of the brain, and it’s vital to figure out how much you trust those ideas before you open your mouth and voice them.

You’ll want to have Confidence. Since there’s not much call for slow wit, you need to be ready with a quip and just as ready to recover if it doesn’t fly. Insecurity is inadmissible; the best insurance is self-assurance.

And the most time-tested way to lessen inhibitions comes via Refreshment, our only slightly euphemistic description of those substances that flow freely at cocktail parties and loosen tongues. This chapter should not be read by children or pregnant women.

These are our conditions for wit. From there, we move on to its purpose.

The Bible and biology agree that our primary job as humans is to propagate the species, so we must highlight wit’s role in Romance. Seduction via repartee is the goal of a thousand sonnets, and a fairly evolutionarily sound one at that: The suitor who can entrance his (or her!) beloved on the fly will probably also be able to improvise ways to protect that future mate from saber-toothed tigers.

Similarly, the element of Charm is key to social advancement in all human societies. If romance is wit directed at one lucky person, charm is a more diffuse sharing of wit with the world.

And should that wit be coupled with ideas on improving society, you have Righteousness. Brilliant ideas need to be delivered brilliantly and wit will convince people to listen.

Then there are the specific life events that call for wit, some obviously and some less so.

The basic human quality of Resilience is how we move forward. When our plans crumble in our hands, we need spontaneous creativity to create new ones.

In everyday Conversation, wit is the salt on the meal, the attribute that makes us want to keep discussing weighty matters.

Wit can be used to cruel ends, but it can just as easily be comprised of Compassion. The two are sides of a coin. We will choose to have it land with the smiling face up.

And finally, in this age of Twitter, the need for Brevity has never been more apparent. Here more than ever, succinct phrasing is the whole point.

A Note on Methods

E. B. White observed that dissecting a joke is like dissecting a frog: No one laughs and the frog dies. On the other hand, a collection of aphorisms can, in the words of aphoristologist James Geary, “fit easily into the overhead compartment of your brain and contain everything you need to get through a rough day at the office or a dark night of the soul.” This book intends to stuff your overhead compartment full of lively frogs. As such, we’ll keep things moving along at a steady clip and sock all the references and further reading in the back.

On occasion, we will have to retell famous quips, but we will do with the understanding that, as New Yorker television critic Emily Nussbaum wrote, “there’s nothing more numbingly Soviet than summarizing comedy.”

Many of the best witticisms are so famous they don’t need repeating, so in those cases we’ll look at the context: How exactly did Churchill have that line about being sober in the morning ready so quickly? (Hint: By stealing it.)

And you’ll find quizzes, checklists and illustrations throughout, all to ensure that the next time you’re in an awkward situation, you’ll have kept these wits about you.

{ ONE }



•   •   •

Can you try to be a wit? The answer is a definite yes. Will your efforts come to anything? The answer is decidedly less certain. The Inverse Law of Repartee has it that the harder an individual attempts to be funny in social situations, the stronger the stink of flop sweat that wafts off that poor soul. Effort and effervescence simply can’t share the same room: It takes hard work to get those bubbles in the Champagne but you don’t want to think about that when you’re popping a bottle.

This is perhaps best illustrated by Ricky Gervais as David Brent in the very first episode of the original U.K. version of The Office. As the boss who’s also a “chilled-out entertainer” shows a new hire around the workplace, he repeatedly stresses how hilarious he is. The Brentmaster General is put to the test when his employee Tim jokingly explains why he has encased his gawky deskmate’s stapler in jelly.

“Gareth, it’s only a trifling matter,” Tim mumbles.

Brent sputters with laughter.

“Here we go!” he chortles as he high-fives Tim. “Always like this!”

“You should probably put him in custardy,” the new hire offers.

“Ha, he’s gonna fit in here!” narrates Brent unnecessarily. “We’re like Vic and Bob,” he says, pointing to Tim and himself in a reference to a British comedy duo, “and one extra one. Oh God!”

“Yeah, I’m more worried, really, about damage to company property, that’s all,” says Gareth.

There’s a long pause and a look of strain on Brent’s face. “I’m just trying,” he says under his breath. “I’m just trying to think of other desserts,” he says.

He does not.

There is another pause to ensure the audience has time to cringe. (This pause lasts forever, and is essentially the gestation period of Ricky Gervais’s career. By the time it ends, he’s a comedy legend.)

Effort has killed wit, and it wasn’t even close. The old Thomas Edison bit about genius being 99 percent perspiration and 1 percent inspiration would appear to be accurate in the ingredients but not the end result: The overwhelming amount of exertion drowns out anything clever and the recipe produces desperation.

But it feels antiquated and elitist to say that true wits are born that way and the rest of us should simply try not to crowd them at cocktail parties, if we’re even invited. Surely in this, the age of the meritocracy, hard work and determination count for something.

Here let us pause to quote The Simpsons:

LENNY: Wow, I’ve never seen you have so many lunch beers before, Homer!

CARL: I concur! (They stare at this unexpected eloquence.) Word-of-the-day calendar. (He holds up an entry for “conquer.”)

So let’s say yes, effort can make you witty—provided it’s deployed correctly and well in advance. Just as no amount of strain and head scratching will help you in the middle of an exam you haven’t studied for, there’s no sense racking the old brain for a comeback that isn’t there. And as you never know when you’ll need a clever retort, there’s no time like the present to start preparing. But how? You can begin by acting like an annoying bird.

The Magpie Mind

The magpie is perhaps the perfect mascot for wit. It is reputed to be one of the most intelligent of all animals, one of the only birds capable of recognizing its own reflection in the mirror and grieving for lost comrades. Less impressively, the word “magpie” is used to describe someone who chatters noisily. And more to the point, it can describe someone who collects indiscriminately, the sort of person who in an extreme case would be featured on a hoarding reality show.

This sort of collecting is where wit must begin, and we can look to the beginning of a Great Wit’s career to see the magpie mind at work. Tom Stoppard, the English playwright and inveterate improver of Hollywood screenplays, began his literary career with the 1966 novel Lord Malquist & Mr. Moon. In a 2005 reissue, Stoppard used a new introduction to shed some light on his early creative process.

Table of Contents

Introduction ix

1 Hustle 1

2 Flow 19

3 Intuition 39

4 Confidence 59

5 Refreshment 77

6 Righteousness 95

7 Charm 109

8 Romance 121

9 Resilience 137

10 Compassion 155

11 Conversation 171

12 Brevity 187

Wit's End 205

Acknowledgments 213

References 215

Index 221

What People are Saying About This

From the Publisher

Elements of Wit promises to teach the wit-deprived hordes how to become modern-day Oscar Wildes and Dorothy Parker…An entertaining book that…will inspire his customers to read as widely as possible and, with the help of a few martinis, crack a little wiser than before.”
The Wall Street Journal


From the B&N Reads Blog

Customer Reviews