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How to Be Witty

In his new book, Benjamin Errett collects the sharpest people of all time in order to help people like me figure out how to seduce women. Or something.

by David Whelan
20 November 2014, 2:45pm

Tina Fey and Amy Poehler being witty as fuck at The Oscars. Image ​via Moustache Magazine

This post originally appeared in VICE UK​

When you're not witty, life is garbage. As a kid, I was smashed over the head with a conceptual hammer again and again until my self-confidence was somewhere between my knees and my asshole, as all the sharp kids were given standing ovations for exquisitely timed "your mom" jokes. It was a fucking nightmare, I tell you.

Apparently Benjamin Errett doesn't suffer from this problem. Apparently Errett can knock socks off feet with nothing but a glass of bourbon and a copy of Good Housekeeping. Apparently he's known throughout the National Post as the Grandmaster Flash of the pithy remark.

In his new book Elements of Wit: Mastering the Art of Being Interesting, Errett collects the sharpest people of all time—your Wildes, your Louis CKs, your Rebecca Northans—in order to help people like me figure out how to seduce women. Er, I mean, make my friends laugh so hard they piss themselves.

I tracked him down to somewhere in the outskirts of Toronto to have a really serious discussion about the dichotomy of good and evil, the future of the emoji and The Office.

VICE: Hi Ben. Just a light one to get us started. Can you help people seduce women? Asking for a friend.
Ben Errett: What? I'm not a pick-up artist. I'm a professional writer and scholar.

Ben, please. He's a desperately lonely man. How can he utilize wit to charm?
In the book I talk about Rebecca Northan, who did this show called Blind Date. She's dressed up as a mime, which is a French clown. She randomly selects a male member of the audience, calls them up on stage, sits opposite her and they go on a date.

That sounds horrible.
The funny thing is, the person always ends up looking good. Rebecca's theory is that everyone is interesting.

Bollocks.
It's up to you to find out why they are. Being witty isn't just about a quick mind, it's also about being genuinely interested in your fellow man.

Benjamin Erret. Photo by Alyssa Bistonath

Interested people are interesting people.
My advice for a first date is: Get them talking. A terrible blind date is when someone comes in and tells you what they're looking for. Everyone, fundamentally, just wants to talk about themselves.

Should he get pissed, and build up some Dutch courage?
To a point I've done some science and decided that people are at their wittiest after two drinks. Any more and you lose perspective on yourself.

I'll take note of that.
How did you find out about the book?

Wait a second. Aren't I doing the interview?
I'm just interested.

I'm not sure I'm happy with this role reversal, it feels like going on the bottom after a lifetime of missionary.
I'm not sure I warranted that imagery.

The irony is, Ben, that I write this up later. So you better wind your neck in or I'll give myself all the witty lines.
Two half-wits make a whole, right?

I saw you've got a Socratic dialogue in your first bloody chapter of the book, which renders this interview process pretty null and void. What do you have to say for yourself?
I was looking for a grand unified theory of what makes good things good: the plays of Tom Stoppard, the comedy of Louis CK, the poetry of Patricia Lockwood, Jay Z... And so on and so on. It's not that they're funny, more that they're witty.

A crazy little thing called wit.
Wit is spontaneous creativity. It takes a lot of work to have the material at hand. It is certainly something you can get better at, like painting.

Some artwork from the book, by Sarah Lazarovic 

How would you recommend I got wittier? Should I stand in front of a bathroom mirror each morning firing off one-liners at my reflection?
Just keep quipping until you're exhausted.

I believe that people are born witty and you can't learn it. Is that a witless opinion?
George Bernard Shaw was originally a terrible speaker and about as sharp as a beach pebble, yet over time he worked on it and developed into one of the great wits of his day. Half the battle is accepting that you can learn it.

Wait a fucking second here. Your book can teach people to be witty?
Yes... That's the whole point of this interview, is it not?

Don't rhetorical question me. All I'm saying is, wouldn't it be a nightmare if this book fell into the wrong hands? Like, what if an absolute prick got hold of it and suddenly he's really witty and everyone loves him and you, Ben, have created a monster?
You put something out there and it can be used for good or for evil.

How Zen of you.
I have a chapter on Cruel Wit, which is, in fact, a particularly British connotation of wit.

I'm going to ignore the implications.
The Ricky Gervais strain of Cruel Wit. As a Canadian...

Oh, I was in Toronto this summer!
Dave, have you written a book yet?

No.
Then shut up.

OK.
So, as a Canadian, I have a good vantage point of pervading wit—the American genre and the British. There's an American thought that wit is cruel, that it's snark and inherently bad. I don't think that's correct. It's a very simplistic way of looking at things.

So Americans are simple?
Haha. Never say anything bad about people, that's my motto.

So British wit isn't cruel, then?
If you think of it as an art form—something that can be worked on—there's no reason why it should be bad. Nobody has said: this painting is so mean, this sculpture offends me.

Wit can be used for both evil and good. Except the comment section beneath articles. They're always just mean.
Oh, god. People in the comment section are lovely. Wit makes everything better. Social situations are always improved by a good quip. You can use wit at interviews, on first dates... Winston Churchill stole so many of his best lines.

What?
There are two types of people. Parrots and magpies. Some people just steal their lines, and repeat them. Others hunt out gold.

Yeah, I have a couple of mates who just fire The Office quotes at each other constantly, while I'm basically Alan Partridge.
I'd actually give them a pass for that because The Office is all about quotations and parroting. It's meta.

"Yes I've enjoyed the odd doobie." One of the catalogue of The Office quotes a meta-wit might give on a daily basis 

They're the two smartest people I know. Certainly the smartest people you know.
A couple of chilled out entertainers. A parrot just shoehorns the best lines into a conversation. But it's not wit. Parroting is high school humor.

You see that, lads? You're high school boys. 
Didn't you open with a question about seducing women, though? That's a typical high schooler. Wit is thinking on your feet, of selling something.

Like your body?
Can you type out: "Ben sighs"?

Would the world be a better place if everyone was a little wittier?
At that point, wit moves into empathy. You can have the best wit in the world, but if no one is listening, what's the point?

This is precisely what I say about my Twitter. I never get retweets for my gold.
Have you considered the possibility...

OK, changing topic. Is Barack Obama witty?
For all his rhetorical strength, he isn't known as a wit... Though he's come up with some great one-liners.

You've very carefully walked around saying Barack Obama is not witty. He was pretty good on ​Between Two Ferns.
Look. He's an effortlessly cool man. I will not fall into your trap.

Are emojis wittier than Barack Obama?
Certainly more than you. In fact, I'd say they're definitely witty, the digital future of wit. You can portray a sentiment in one image.

Where does wit come from, do you think?
Ancient Greece considered wit as virtue... But then it sort of disappears. The Middle Ages weren't very witty, what with the Bubonic Plague and all. There was a rebirth during the Enlightenment. In the courts there would be contests for the best ripostes. But then, everyone said so many good things about wit nobody knew what it really was anymore.

Like disco.
Precisely. Then America spread it across the world through motion pictures and online. Right now, the pervading wit is the wit of the United States of the internet.

What?
That's where language, sentiment, and thinking is evolving. Memes are witty.

Wait. Are you saying the modern day wit is "American Wit: Online"?
I mean, the country of the internet.

Thank fuck for that.
Thanks for talking to me, Dave.

Thanks for quipping with me, Ben.

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