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25 Ways To Be Witty

I recently researched the concept of wit, figuring out what made something clever by exhaustively examining famous funny quotes in-depth. Here I present 25 methods, complete with examples of each. If you think that dissecting humor kills it, read no farther. If you’d like an explanation of how wit is effective, keep on going.

Disclaimer: Humor is far too complicated to be fully understood, ever. This is merely 25 different ways that wit, the clever form of humor, can be expressed. There are more.


Different methods of reaching wittiness:

1. Irony
eg. Anyone who goes to a psychiatrist should have his head examined. -Samuel Goldwyn.
Anyone who supports capital punishment should be shot. -Colin Crompton

2. Unusual analogy
eg. Words are, of course, the most powerful drug used by mankind. -Rudyard Kipling
Be like a postage stamp. Stick to one thing until you get there. -Josh Billings
2a. Unusual analogy that is purposefully ridiculous in one way while still making sense in the other.
eg. Marriage has no guarantees. If that’s what you’re looking for, go live with a car battery. -Erma Bombeck

3. Modification of established statement.
3a. Modification of previous statement in conversation
eg. “Driving her or something?” “Noticing her haircut or something.” -Frazz strip on why Frazz has a note about his girlfriend’s hair appointment.
3b. Modification of well-known analogy
eg. Laughter is the shortest distance between two people. -Victor Borge
What’s the use of happiness? It can’t buy you money. -Henny Youngman
Familiarity breeds contempt – and children. -Mark Twain
Where there’s a will, there are five hundred relatives.
Grant me the senility to forget the people I never liked anyway, the good fortune to run into the ones I do, and the eyesight to tell the difference. -Anon
3c. Modification of well-known quotation
3d. Modification of well-known joke
3e. Modification of cliche
eg. Anyone who goes to a psychiatrist should have his head examined. -Samuel Goldwyn.
Give a man a beer, he’ll waste an hour. Teach a man to brew, he’ll waste a lifetime.
3f. Modification of well-known concept.
I was arrested for selling illegal-sized paper.

4. Statements that show original and bizarre ideas.
eg. Sometimes I wonder if men and women really suit each other. Perhaps they should live next door and just visit now and then. -Katharine Hepburn

Note: a good way to cultivate more conversation as other wits can respond better to an entire concept than to a single joke.

5. Hyperbole
eg. When women are depressed they either eat or go shopping. Men invade another country. -Elaine Boosler
Note: most effective when used caustically.

6. Prove something true through proving that the opposite applies to everything else.
eg. I am free of all prejudices. I hate everyone equally. -WC Fields.
Note: This one’s tough to explain. Hopefully the example makes it clearer. It isn’t too hard once you understand it, I promise.
6a. Prove something true through showing the opposite applies to its opposite; parallelism
eg. Genius may have its limitations, but stupidity is not thus handicapped

7. Subvert expectations about the definition of a particular word or phrase
eg. My reputation grows with every failure. -George Bernard Shaw
England and America are two countries divided by a common language. -George Bernard Shaw
Familiarity breeds contempt – and children. -Mark Twain
Giving up smoking is the easiest thing in the world. I know, because I’ve done it thousands of times. -Mark Twain
Truth is the most valuable thing we have..Let us economize it. -Mark Twain
Experience is the name everyone gives to their mistakes. -Oscar Wilde
Democracy consists of choosing your dictators, after they’ve told you what it is you want to hear. -Alan Coren
If I am what I eat then I am cheap, quick and easy. – Anonymous
Diplomacy Is Saying “Nice Doggy” Until You Find A Rock
Diplomacy is the art of letting someone else get your way.
90% of communication is body language. The rest is just hopeful guesses.
Where there’s a will, there are five hundred relatives.
A new study found that the average child is more likely to own a cell phone than a book. I guess that would explain why he’s average. -Jimmy Fallon
My girlfriend asked me how long I was going to be gone on this tour. I said, “the whole time.” -Steven Wright
It’s not hard to meet expenses, they’re everywhere.

8. Understate
eg. The report of my death was an exaggeration. -Mark Twain

9. Making a point by wording it as the opposite of another, more conventional, matter.
eg. Don’t worry about avoiding temptation…as you grow older, it will avoid you. -Winston Churchill
There is no way to peace. Peace is the way. -A J Muste
It is much more important to know what sort of patient has a disease than what sort of disease a patient has. -Sir William Osler
And in the end it’s not the years in your life that count. It’s the life in your years. -Abraham Lincoln
One should eat to live, and not live to eat. -Moliere
Not everything that is faced can be changed, but nothing can be changed until it is faced. -James Baldwin
Life is what you make it, don’t let it make you or your life is no longer yours.
Note: The point will end up worded in an odd way; at best unique and at worst in a way that barely makes sense. As long as you get the point across and it’s intelligent, people won’t care if it’s difficult to understand. The parallel nature of the opposite statements is what matters here.
9a. Making a point by wording it as the opposite of more conventional matter while using similar words or phrases.
eg. Some cause happiness wherever they go, others whenever they go. -Oscar Wilde

10. Use opposites to get strong contrasts.
eg. Diplomacy is to do and say the nastiest thing in the nicest way. -Isaac Goldberg
Evening news is where they begin with ‘Good evening’, and then proceed to tell you why it isn’t.
10a. Set up a false dichotomy with your opposite concepts.
eg. There are only two ways to live your life. One is as though nothing is a miracle. The other is as though everything is a miracle. -Albert Einstein

11. Make a paradox revolving around the concept of ‘nothing’.
eg. I’m addicted to placebos. I’d give them up, but it wouldn’t make any difference. -Steven Wright
I love talking about nothing, Father. It’s the only thing I know anything about. -Lord Goring, An Ideal Husband
Note: Paradoxes are one of the few examples of wit that really isn’t very intelligent.

12. Imply an insult.
eg. One of the penalties for refusing to participate in politics is that you end up being governed by your inferiors. -Plato

13. Say something very obvious as if it weren’t.
eg. My formula for living is quite simple. I get up in the morning and I go to bed at night. In between, I occupy myself as best I can. -Cary Grant

14. Contradict yourself using different wording.
eg. I was trying to daydream, but my mind kept wandering. -Steven Wright
If I promise to miss you will you go away? – Anonymous
14a. Allow the contradiction to be inferred.
eg. Doctors say I have a multiple personality, but we don’t agree with that.

15. Use format “X plus Y minus X”
eg. Two things are infinite: the universe and human stupidity; and I’m not sure about the universe. -Albert Einstein

16. Parallel construction
eg. If you obey all the rules, you miss all the fun. – Katherine Hepburn
Tact is the art of making a point without making an enemy.-Howard W. Newton
Note: the last example includes a play on the word “making.” The pun is heightened by the parallel construction.

17. Show cause and effect; format X, Y, then X and Y
eg. Here’s all you have to know about men and women: women are crazy, men are stupid. And the main reason women are crazy is that men are stupid. – George Carlin
Note: it’s witty because the repetitiveness contrasts with the new meaning.

18. Ridiculous yet logical conclusions based on incorrect suppositions.
eg. Students at school were asked to write about the harmful environmental effects of oil on fish. One 11-year old wrote, “When my mom opened a tin of sardines last night it was full of oil and all the sardines were dead.”

19. Allow the final connection to be made by the listener.
eg. Smoking in the lavatories is prohibited. Any person caught smoking in the lavatories will be asked to leave the plane immediately.
The letters T and G are very close to each other on a keyboard. This recently became all too apparent to me and consequently I will never be ending a work email with the phrase “Regards” again.
Thank you for your cooperation and vice versa. -Eugene Ormandy

20. Act as if something bad were actually good. (accepting that it’s bad) (Or vice versa)
eg. Never make the same mistake twice or you’ll never get around to all of them.
There is nothing so annoying as to have two people talking when you’re busy interrupting. -Mark Twain

21. Act as if something bad were actually good. (in order to show it really is good) (Or vice versa)
eg. Progress might have been alright once, but it has gone on too long. -Ogden Nash

Methods of heightening wittiness:

22. Ironic use of assumed obviousness about something abnormal
eg. Words are, of course, the most powerful drug used by mankind.
Rudyard Kipling

23. Verbosity
eg. Human beings, who are almost unique in having the ability to learn from the experience of others, are also remarkable for their apparent disinclination to do so. -Douglas Adams

24. Put an non-witty part first.
eg. The secret of a good sermon is to have a good beginning and a good ending; and to have the two as close together as possible. -George Burns and By all means, marry. If you get a good wife, you’ll become happy; if you get a bad one, you’ll become a philosopher. -Socrates
These quotes wouldn’t be as funny if they were “The secret of a good sermon is to put the beginning and end as close as possible” and “If you get a bad wife, you’ll become a philosopher.”

Wit used in conversation:

25. Find a way to change the meaning of a word.
eg. “What do you want?” “I want you to think.” “But what do you want me to think?”
The second speaker has changed the definition of “want” given by the first speaker.

The lines between these different categories of wit are blurry. Subverting something, implying something, subverting something by implying something else; it can be tough to stick everything in boxes. However, the same themes crop up pretty often. For example, a large amount of wit is based on subverting presuppositions; ‘surprising’ the audience. Wit is word-based, too, as these subversions and implications rely on an accurate use of the English language (parallel construction and cause-and-effect, for example). The more well-versed, the better you’ll be at synthesizing wit. To be witty, use diverse concepts to surprise the audience. Which, coincidentally, is the secret to creativity.


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