Wit is one of the 10 words investigated by C.S. Lewis in his Studies in Words. He tells us that “wit” was first used to connote “mind, reason, intelligence,” fundamental good sense. Then its meaning changed to suggest a person’s entire mental make-up. Then it rose in aesthetic significance to convey the imaginative skill of poets and other artists. “I take it that wit in the sense now current means that sort of mental agility or gymnastic which uses language as the principal equipment of its gymnasium,” Lewis wrote. The word in our day describes all verbal cleverness, usually of the kind delivered orally. Pun, epigram, repartee, amusing paradox, surprising juxtaposition—these are among the verbal machines on which, to stay with Lewis’s gymnasium metaphor, wit works out.

In imaginative writing—novels, movies, plays, poems—wit in this sense is most frequently found in clever dialogue; or in lyrics of the kind Ira Gershwin, Cole Porter, and Lorenz Hart wrote; or in works of nonfiction in amusing formulations. Falstaff, Shakespeare’s wittiest character, was himself an artist of verbal wit, the Falstaff who said, “I am not only witty in myself, but the cause that wit is in other men.” Written, or literary, wit had a good run in the 18th century: in the plays of William Congreve and Richard Sheridan, in the poetry of Alexander Pope, and in the various works of Jonathan Swift. Wit plays throughout Edward Gibbon’s Decline and Fall, as in his sentence on the Emperor Gordian II: “Twenty-two acknowledged concubines, and a library of sixty-two thousand volumes, attested the variety of his inclinations, and from the productions which he left behind him, it appears that the former as well as the latter were designed for use rather than ostentation.”

Wit has come to find its consummation in conversation. Talk is now its main medium, unrehearsed talk in which someone says something so dazzling as to be memorable. Wit is not, as in writing, evoked in tranquility, but is instead, as Benjamin Errett defines it in Elements of Wit,¹ “spontaneous creativity.” Wit, though generally humorous, needs to be distinguished from humor, which can be created at leisure, polished through revision, and even tested upon focus groups to insure that it works. “Unlike humor,” Errett writes, “wit is a speed game.”

That wit wasn’t always what it is today, a form of brilliant and memorable talk, is attested by such idioms and words as “at wit’s end,” “dimwit,” and “half-wit.” All of these denote the connection between wit and common sense. The dimwit and the half-wit are of course deficient in such sense; to be at wit’s end denotes finding oneself in a situation in which normal common sense is of no avail. Today one is more likely to see wit applied as a label to public personalities who are thought to be clever; for example, that well-known wit…Joseph Epstein.

I have never thought myself a wit, but some years ago, in reviewing a book of mine on snobbery, William F. Buckley Jr. called me “perhaps the wittiest writer (working in his genre) alive, the funniest since Randall Jarrell.” The quotation has turned up as the last line in my Wikipedia entry, with the result that, on the rare occasions when I give a talk or lecture, I am generally introduced as—all qualifications dropped—“the wittiest writer alive.” When this occurs, I hasten to tell my audience that I hope they will not be disappointed when, after four or five minutes into my talk, they come to find Mr. Buckley’s generous contention not merely dubious but definitively disproved.

I wish it were otherwise, but I am not witty. What I believe I am is mildly charming. Charm is the ability to arouse approval for oneself, to seem socially adept. Wit is a more precise skill. Oscar Levant claimed never “to stoop to charm.” Unlike charming people, witty ones can offend, and often don’t care if they do. I myself prefer to be liked rather than admired for such shreds of wit as I do possess.

As a would-be charmer, I have over the years built up a store of anecdotes and fairly surefire jokes that I can trot out when needed. I can drop an interesting quotation with what I hope is lightness of touch. I am alert to the comedy of language and often play off its absurdities, subverting clichés, twisting idioms, doing English in foreign accents. Like the character Sloppy reading the newspapers in Our Mutual Friend, I “do the police in different voices.” I also have a taste for whimsy. Late one afternoon when my sons were growing up, I was at the stove making Italian meat sauce and asked them, as I put a spoonful of sugar into the pot, what movie my doing this reminded them of: the answer was Absorba the Grease after, of course, Zorba the Greek. (My children’s upbringing, plainly, wasn’t an easy one.) None of this, strictly speaking, is wit.

Wit, when available to me at all, is possible only when I can create it in tranquility, on the page, or now increasingly on the computer screen, where there is ample room for rehearsal, as aspiring but inadequate wits might think of revision. But wit in its sense of quick and amusing and often devastating riposte, is not my speciality. Esprit d’escalier, or staircase wit, the witty response that occurs to one too late, is for me rather closer to it.

During my last teaching days, in a course I taught on Henry James, I asked a student named Jonathan Stern to describe the character Gilbert Osmond from James’s The Portrait of a Lady. Without the least intent to offend his teacher or evoke laughter from his classmates, he declared Osmond “an asshole.” I seemed to be the only one in the room shocked by his response, and I told him, calmly, that I would allow each student in the course one such word, and he had now used up his allowance. Only later, leaving class, actually walking down the stairs, did it occur to me that what I should have said was, “I’m pleased, Mr. Stern, that I didn’t ask you to describe Oedipus Rex.”

I have been in the regular company of only one genuinely witty man, my friend Edward Shils. When I told Edward of a mutual acquaintance of ours having recently informed me that, in Prague, where he grew up, his father never shaved himself but always had a barber come in to do so, Edward replied, “You know, Joseph, the truth more likely is that his father shaved his mother.” I once introduced Edward to the English journalist Henry Fairlie. Edward mentioned that he had heard Fairlie had become a socialist, and asked him to explain how this came about. Fairlie replied that he owed his conversion to hearing Michael Harrington speak in Chicago. “Michael Harrington in Chicago?” said Edward. “Surely a case of worst comes to worst.” Of David Reisman, his colleague at the University of Chicago, who attempted to pass himself off as a WASP, Edward remarked, “I’ll say this for David, he’s never taken undue advantage of being Jewish.”

Edward Shils taught half the year at Cambridge in England, a country where the tradition for wit is stronger than it has been in America. Maurice Bowra exemplified high-table Oxbridge wit. When someone told Bowra that the woman he was courting, the niece of Sir Thomas Beecham, was a lesbian, Bowra, himself reputed to be homosexual, replied, “Buggers can’t be choosers.” Noël Coward noted that “having to read footnotes resembles having to go downstairs to answer the door while in the midst of making love.” Evelyn Waugh, surely the wittiest novelist of the past century, in World War II, coming out of a bunker during a German bombing of Yugoslavia, looked up at the sky raining enemy bombs and remarked, “Like everything German, vastly overdone.” Kingsley Amis said that “laziness has become the chief characteristic of journalism, displacing incompetence.” From Beyond the Fringe to Monty Python, English humor at its higher echelons featured wit.

Only a few traces of wit show up in Edward Shils’s writing. No one knew about it who didn’t know him personally; knowledge of his quick cleverness was restricted to his students and his friends. The great wits of the past century found means to have their witty remarks broadcast well beyond their social circle. Among the wits discussed in Errett’s Elements of Wit are Sydney Smith, Mark Twain, Oscar Wilde, Dorothy Parker, Groucho Marx, Winston Churchill, Mae West, George Bernard Shaw, Robert Benchley, and Oscar Levant. Missing are H.L. Mencken, W.C. Fields, Noël Coward, Billy Wilder, and George S. Kaufman. An obvious neurotic, Kaufman, when asked why he left psychotherapy after only a few sessions, claimed, “the guy asked too many goddamn personal questions.” A relentless philanderer, Kaufman told Irving Berlin that he liked his song “Always,” but would prefer it if he changed the title to “Thursdays.”

I learned about these Kaufman quips from a biography of Kaufman by Howard Teichmann. Many of Churchill’s best mots are recorded in other people’s memoirs. Oscar Wilde made a show of his epigrams, paradoxes, and comic aphorisms (“A cynic is someone who knows the price of everything and the value of nothing”) while on tour in America. Traveling round the United States, he put himself perpetually on exhibit, his witty remarks picked up by the press that accompanied him; they accompanied him, in fact, chiefly because his remarks made good copy. The wittiest things said during the 1920s and ’30s at the Algonquin Round Table found their way into Franklin Pierce Adams’s “Conning Tower” column in the old New York World and later the New York Herald-Tribune. Oscar Levant, who let it all hang out before the phrase was invented, made many of his more outlandish remarks on the old Jack Paar Show, and on his own talk show before he was fired for going too far with a joke about Arthur Miller and Marilyn Monroe, oral sex, and keeping kosher. Wits without fame do not get their brilliant lines recorded, at least not in the past they didn’t. The Internet, as we shall see, is changing this, at least somewhat.

Elements of Wit, like the Strunk and White book on composition after which it is titled, is pedagogical in intent. The book sets out on the project of teaching wit by precept and example. Along with offering mini-profiles of some famous wits of the past and present, Benjamin Errett (a Canadian journalist) provides discussion of the role of wit in improv theater; the effect of alcohol on lubricating and loosening wit; and the need for brevity, the soul, after all, of wit. He quotes from various studies on wit and humor; and, inevitably, as is de rigueur these days, he brings in far-from-convincing brain studies and ponders the connection of the physiology of the brain to the creation of wit.

At one point Errett provides a list of 11 contemporary wits. The list includes Russell Brand, Gail Collins, Louis C.K., Nora Ephron, Tina Fey, Christopher Hitchens, Fran Lebowitz, Steve Martin, Amy Poehler, Tom Stoppard, and Kanye West. The rapper Jay-Z, to whom he devotes several pages, is another of his models for wit in action.

Not all these contemporary wits pass Errett’s definition of wit as “spontaneous creation.” We learn that Steve Martin worked out his stand-up comedian’s bits over time, so that little of the finished product of his wit can be said to have been spontaneous. Much of Tina Fey’s wit was scripted for her television shows. Is Russell Brand sufficiently amusing to earn the title? Louis C.K. passes for witty if one’s taste runs to masturbation jokes. Jay-Z’s rap music, much of it created at the moment of recording, may be spontaneous, but does it truly qualify as witty? Lots of things—sarcasm, invective, obscenity—can be created spontaneously without being witty.

Would Christopher Hitchens have seemed witty without an English accent? Wasn’t Hitchens, a man who gave the title The Missionary Position to his book-length attack on Mother Teresa, more a provocateur than a wit? Is there a great difference between Nora Ephron’s complaining about age doing in her neck and the newspaper columnist Erma Bombeck’s writing about the travails of being a housewife—any difference, really, apart from Ephron having had a fancier address and a flashier social set? In the few interviews I have seen with Tom Stoppard, his seriousness easily eclipses his wit. Are these cavils merely? Or do they suggest the lowering of standards on what passes for wit in our time?

Another of Errett’s definitions of wit is “good sense that sparkles.” He prefers cheerful wit; like Joseph Addison, whom he quotes, his taste runs to wit that “gives delight and surprise.” Errett defines snark as wit that “scorches.” Yet much wit is dark, and lots of the richest wit is outrageous. Think of the late Sue Mengers, the movie agent, who walked into a less than exclusive Hollywood party and remarked to a friend: “Schindler’s B-list.” After the Charles Manson murders, Mengers is supposed to have told her client Barbra Streisand, “Don’t worry, honey, they’re only killing bit players.” Saul Bellow, whose propensity for saying witty things sometimes got him in trouble, wrote a story called “Him with His Foot in His Mouth,” about a man who regularly wounded people because he could not control making offensively witty remarks. The wittiest remark in the story belongs not to the story’s narrator but to an older scholar whose boredom is obvious when the narrator reads his scholarly article to him. The narrator asks if he is causing the scholar to fall asleep, to which the scholar answers, “No, you’re keeping me awake.”

Wit is meant to be pleasing, but as often as not it can be cruel. John Simon makes the point that humor is “basically good natured and often directed toward oneself,” while wit is “aggressive, often destructive…and almost always directed at others.” When Clare Boothe Luce held open a door for Dorothy Parker and said “Age before beauty,” Miss Parker, passing through, replied, “Pearls before swine.” Such examples of aggressive wit are generally the most memorable. What stays in the mind are the stabbing riposte, the ripping repartee, the punishing put-down.

Errett bridles at the thought that wit is no more than “clever nastiness.” In his view “wit is the thought process that generates truly funny observations, as well as the most incisive comments, lasting quips, and brilliant asides.” Perhaps his cheerful outlook on the subject of wit compelled him to neglect entirely Gore Vidal, a figure often on the list of contemporary wits. If Vidal had had a motto, it might have been, “If you can’t say something nasty, then say nothing at all.” But Vidal fails the first test of wittiness, which is unpredictability. Predictability is death for wit, and Vidal’s wit was always predictable. Apart from those of his mots devoted to slightly perverse sexual matters—“I am all for bringing back the birch, but only between consenting adults,” is an example—most of the rest are about the crummy, inane, deceitful plutocracy that for him was America. Vidal paraded this merchandise on every talk show that would have him. “I never miss a chance to have sex or appear on television” is another of his mots. One knew what was coming before he opened his mouth; it was only a question of how mean he would be.

Defying anticipation in a way that is both amusing and causing one’s auditors to take thought is one of the hallmarks of genuine wit. Of Doris Day, Oscar Levant remarked: “I knew her before she became a virgin.” Fran Lebowitz, remarking that it’s impossible not to notice that children in America are more and more protected and to a later and later age, claimed that “the man who invents the first shaving mirror for strollers is going to make a fortune.”

If asked to choose an ideal, a perfect, wit, my candidate would be Sydney Smith, the early-19th-century clergyman who was one of the founders of the Edinburgh Review. Errett devotes a few sparse paragraphs to Smith in his book, but not enough to capture the splendor of a true wit at work. The actress Fannie Kemble wrote that “the fanciful and inexhaustible humorous drollery of his [Smith’s] conversation among his intimates can never be adequately rendered or reproduced.” A young Benjamin Disraeli, himself a famously witty man, was once seated next to Sydney Smith at a dinner party and found him “delightful,” adding, “I don’t remember a more agreeable party.” Others reported that they could not remember what he said because in his company they laughed so much. Sydney Smith spoke almost exclusively in mots, lovely metaphors, witty formulations. He said of the garrulous Lord Macaulay that his conversation contained “some gorgeous flashes of silence.” He likened his life as a reviewer and sometimes polemicist to that of a razor, always “either in hot water or scrapes.” Of two women screaming insults at each other from their apartments across a narrow street, he said: “Those two women will never agree. They are arguing from different premises.”

Does wit come naturally, or can one acquire it through effort and training? The assumption behind Elements of Wit is that it can be acquired. “Creative spontaneity,” Errett writes, “takes practice.” Yet his book casts doubt on the notion that wit, even among the most famous wits, really is created spontaneously. Winston Churchill, he informs us, was a reader of Bartlett’s Familiar Quotations and in search of material for conversation sedulously read jokes columns in newspapers. “His magpie mind drew from books, film, media, and anywhere else he read, heard, or saw a line worth repeating.” Errett does not mention La Rochefoucauld, the world’s wittiest aphorist, who worked with his friend and lover Madame de Lafayette at burnishing his aphorisms before bringing them out for display in the salons of Mme. de Rambouillet and Mme. de Sablé, where they were further polished. Might it be that a great deal of what passes for wit—for, in Errett’s term, “spontaneous creation”—isn’t spontaneous at all but has been carefully worked up beforehand?

The leading forum for the display of wit in our days ought to be the television talk show. Yet one doesn’t think of any of the talk-show hosts, now and in the past, as especially witty, if only because all employed or currently employ a cadre of writers who supply them with much of the material that passes for their own wit, though some among them ad lib cleverly. The same, one suspects, may well be true of ostensibly witty talk-show guests, who are often coached about what questions they will be asked and what subjects they can expect to discuss.

Are dazzling wits possible in our day? No reason why they shouldn’t be, though how we might come to know about them is unclear. Might such a wit be someone out there sending witty tweets to friends? The form of the tweet, with its limit of 140 characters, could work to force a tweeter into concise wit. The closing pages of The Elements of Wit offer some amusing tweets. “So now Blagojevich has been double impeached, which sounds like a Ben & Jerry flavor” isn’t at all bad; nor is this, “the most beautiful tweet ever tweeted,” as chosen by Stephen Fry: “I believe we can build a better world! Of course, it’ll take a whole lot of rock, water & dirt. Also not sure where to put it.” I do not myself tweet—to do so would be unseemly in a man of my august age—but I have followed a couple of friends on Twitter, one of whose tweets are consistently amusing. If Twitter does create a new conveyance for wit, a new word for those who display their wit on it will be required—a twit-wit, perhaps.

As for whether wit can be taught, my own sense is that it cannot. Honed and sharpened it can be, but it has to be there to begin with. As Aristotle, in the Poetics, said about metaphor, so one might say about wit: “It is the one thing that cannot be learned; it is also a sign of genius.” Wit, in other words, is a gift. But without an interesting point of view, a detached angle on life, a wide culture, the gift will come to naught. Wit is the expression of those who understand and are able to formulate and deflate in a pleasing way what they see as pretension, false self-esteem, empty ambition, snobbery, and much else worth mocking in life. We need wits on the scene, like doctors on the case. Without them to remind us how absurd we can be, we fall into the grave danger of taking ourselves altogether too seriously.

1 Perigee Trade, 256 pages