The nine defining qualities of cool

The author of How to be Cool explores the concept, whether it can be taught, its roots and evolution and reveals the coolest person ever


There’s a story I remember being told by a friend when I was at school. Back in the 1970s, the actor Clint Eastwood – known for playing bestubbled, hard-bitten heroes – was being interviewed by the chat show host Terry Wogan. “So come on, Clint,” Wogan asked him chummily. “How is it that you’re so cool?” To which Eastwood responded by taking out a cigarette, flicking it up in the air, striking a match on the heel of his shoe, and then lighting the cigarette while catching it between his lips on its descent. After taking the first puff, he growled, “I dunno, Terry. I guess it just happened that way.”

When I was told that story, I thought it was about the coolest thing I’d ever heard. So my first advice to anyone who wishes to know how to be cool is: take up smoking, learn a party trick and maybe develop a trademark growl.

I’m kidding.

So what is my first advice? These are deep waters. You don’t want to plunge right in.

Before we go any further, there are four immediate questions raised by the very idea of a book bearing the brazen title of How to Be Cool, and they are these:

1) What is cool?

2) Where did it come from?

3) Has it changed?

4) Can it be taught?

With your permission, I’ll give the brief, knee-jerk answers to these questions, and then offer my longer, more considered responses. The brief, knee-jerk answers are as follows.

“Cool” can’t really be defined but it has something to do with style and something to do with emotional composure (aka “keeping your cool”). It arose out of the New York jazz music scene and was taken up by Hollywood in the 1950s in movies featuring cool characters played by the likes of James Dean and Marlon Brando. The attitude became so popular with the young that the word “cool” came to mean little more than “good”. Yet in certain contexts it still retains something close to its earlier meaning. And this is something that cannot be taught. There are cool people and there are uncool people. You either have it or you don’t.

Consider those claims, particularly the last one. Now I accept that there are certain physical attributes that can’t be taught. You can’t teach someone to be tall, for example, although it might be fun to try. But when it comes to character, almost anything can be taught. Virtue. Courage. And, yes, coolness too. So keep an open mind (an essential prerequisite of cool), read on, and see if you’re persuaded.

1) What is cool?

I’m going to come right out and say it. I have identified the NINE DEFINING QUALITIES OF COOL. These are the Nine Qualities that you need to know. You won’t find them anywhere else. How did I come up with them? That will be revealed in due course. But for now, consider the Nine. How many have you got taped?









Emotional self-control

We’d better unpack these a little. Style: You’re physically co-ordinated and know how to dress. Rebellion: You question authority. Recklessness: You value present pleasure over future health. Rootlessness: You travel. A lot. Promiscuity/ Celibacy: The point is that you’re not into the whole monogamous commitment thing. Self-expression: You’re somehow an artist. Flamboyance/Austerity: Either will do. Taciturnity/ Eloquence: You make words count. Emotional self-control: You’re pretty relaxed. You rarely lose it.

So how did I compile this list, these Nine Defining Qualities of Cool? I’m going to answer that. I am, but not straight away. We don’t want to get bogged down in methodology.

2) Where did it come from?

Coolness isn’t a 20th-century invention but it is a 20th-century phenomenon. That’s to say, if you look back through the centuries, you can find examples of people who had some or most of the Nine Qualities. In the Middle Ages. In Ancient Greece and Rome. There were probably cavemen who were cool. In fact, now I come to think of it, there definitely were.

But it earned a name only in the 20th century when, for a perfect storm of reasons, an anti-establishment attitude began to exert an extraordinary mass influence among the young. This was an unprecedented cultural shift, which amounted to the rise of a new value system to rival those offered by morality or worldly success. We’d had rich. We’d had good. Now here was cool, which was something completely different.

The question of where cool came from is one that scholars have tried to answer literally, which is to say geographically. The art historian Robert Farris Thompson, for example, has a theory that its true origin was a quality called itutu (a blend of cool-headedness, playfulness and generosity) that was developed by the Yoruba and Ibo peoples of West Africa. It was carried to America in the 19th-century slave ships, where it hardened into a stance of silent but seething defiance.

Then, amid the burgeoning jazz music scene of 1930s New York, there was (we are told) a practice in some clubs of throwing open the windows in the early hours of the morning to let the cool air in, and blow away the smoke of a thousand cigarettes. As a result, the small-hours jazz playing style, which tended to be pretty laid-back, became known as “cool jazz”. And later that “coolness” somehow got linked to the rebellious attitude that was rooted in West African itutu. None of this impresses me much. The meaning of a word isn’t defined by origin but by usage. And in any case, where do they take us, these hypothetical theories that are at least partly based on anecdote? More interesting, I think, is to consider where cool came from in the sense of what caused it. What were the conditions, the catalysts?

This isn’t, thank god, an academic study, providing rigorous proofs and scrupulous sources. A really thorough account of the rise of cool would need to be practically a roadmap to 20th-century culture. It would include every B-road, byway and lay-by. All we’re aiming to do here is to find the right motorway and stick to it.

For the record, though, a comprehensive catalogue of the “inciting incidents” (to use a screenwriting term) that combined to create cool would include not only the suppressed resentment of the cotton-picker (American slavery) and the relaxed intensity of musical improvisation (jazz and blues), but also the breezy confidence of the flapper (first-wave feminism) and the conservative prosperity of postwar America, which gave the young something to rebel against (juvenile delinquency). The historian Paul Fussell suggested that the horrors of the first World War had such a traumatic impact on the western psyche that, ever afterwards, the dominant cultural and philosophical mode became one of irony, which avoided emotion and rejected the old value systems. Coolness, to extend Fussell’s thesis, was to the second World War what irony was to the First. Let’s say that it was irony with style.

In an influential essay published in 1957, the celebrity novelist Norman Mailer argued that coolness was a philosophical position: a bleak existential reaction to the barbarity of the Holocaust on the one hand, and the fear of nuclear catastrophe on the other. With an unforgivable past and an unliveable future, there was nowhere left to exist but in the present. Mailer refers to this, rather startlingly, as the search for “orgasm”. One of the dangers of writing about cool is that it’s easy to get carried away. But, as often with Mailer, in the general cut and thrust of his theory, he may have had a point.

3) Has it changed?

The Austrian philosopher Ludwig Wittgenstein said, “Whereof one cannot speak, thereof one must be silent.” But if that were taken seriously, there would be no such thing as journalism. In any case, I’ve always suspected that the old dog was just trying to get everyone to shut up, so that he could bang on uninterrupted. One may not, it’s true, be able to speak with absolute authority about the meaning of the word cool, but that doesn’t mean that what one says won’t be worth saying. From its origins as a term to signify the opposite of warm (a cool breeze), the word has progressed and digressed through a bewildering range of meanings.

Here’s a list, which I offer in roughly chronological order. We’ve had flapper cool, jazz cool, blues cool, Beatnik cool, Hollywood cool (aka juvenile delinquency cool), rock ‘n’ roll cool, hippy cool (aka counterculture cool), punk cool, yuppie cool, hip hop cool, grunge cool, hipster cool and geek cool.

There’s a fear here of having left something out. It reminds me of the scene in Blackadder the Third when Dr Johnson proudly presents his newly finished Dictionary to the Prince Regent, declaring that it contains every word in the English language. In that case, says Blackadder, may I present my most enthusiastic “contrafibularities”? Similarly, I brace wearily for the moment when someone mutters, “I hope you’ve included ‘murk’,” or else exclaims in outrage, “Don’t tell me you’ve left out the stuntman Barry Gawithers?”

Inevitably, there will be omissions. No doubt there will be confusions too. There usually are, when it comes to cool. That’s one of the cool things about it.

Cool refuses to be defined. It hates labels, even designer ones. And even cool people can sometimes get it wrong. The comedian Lenny Bruce liked to tell the story of the time he saw a guy with a beard in a coffee shop and went up to him and said, “What’s shaking, baby?” The man turned out to be a rabbi. And rabbis can’t be cool, can they?

Not easily, no. In whatever era we’re talking about, coolness defines itself in opposition to convention and authority. But here’s the thing. If it succeeds – which is to say, if it catches on, as cool caught on in the 20th century – then it becomes more conventional, and therefore proportionately less cool. Several of my Nine Defining Qualities of Cool have been at least partly absorbed into the mainstream. I’m thinking particularly of rebellion, recklessness, promiscuity and self-expression.

Does this then mean that cool is dead? Does it mean that now, in order to be cool, you have to be uncool? I don’t think so. If you accept that cool defines itself in opposition to convention, then it will be around for as long as convention is around. And convention isn’t going anywhere. Or at least, it isn’t going far. The thing, you see, about convention is that it’s conventional. (It just can’t help itself.) It will always revert, sooner or later, to its natural position, which is to align itself with a value system that prioritises the security of health and home, the rewards of monogamous commitment, and the prospect of a steady job.

What this means is that there will always be a central core of cool, which defines itself against this central core of convention. I guess you could call it Classic Cool. It is this – this recurring idea of Classic Cool – that How to Be Cool is focused on.

4) Can it be taught?

The great myth of cool is that it’s effortless. It’s a master-stroke, this, like the Devil’s success in persuading people that he doesn’t exist. By persuading people that it’s effortless, cool looks even cooler, while also ensuring that few will attempt to up their cool quotient and challenge it for position. Nevertheless a curious game of Grandmother’s Footsteps still takes place, by which those wishing to become cooler will creep forward, ready to freeze at any moment, should Classic Cool suddenly whirl round and spot them trying.

But try they do and try they always have. Anyone repeating the self-serving myth of effortless cool, I would first congratulate for understanding the First Rule of Coolness, which is to deny that there are any rules. Then I would point them in the direction of some of those who are widely regarded as the coolest of the cool. In almost every case, it’s clear that they themselves learnt from cool role models, sometimes quite deliberately. Early in his career, Paul Newman was thought to be copying James Dean. James Dean was thought to have copied Marlon Brando. Muhammad Ali confessed that he had been inspired by the flair and flamboyance of the boxer Jack Johnson. David Bowie wrote songs acknowledging his admiration for Andy Warhol and Bob Dylan. As a young man, the aspirant author Hunter S Thompson typed out the entirety of Ernest Hemingway’s novel A Farewell to Arms. That’s right. He typed the whole thing out, word for word, punctuation mark for punctuation mark, in the hope of learning what it felt like to write a cool masterpiece. There was nothing effortless about that.

So the First Rule of Coolness is to deny that there are any rules.

The Second Rule of Coolness is to choose your role models.

This is the method. We’re not dealing, like some self-help books, in lessons and exercises. There is no homework. What How to Be Cool does is present a selection of possible role models (Idols) and relevant themes (Ideas and Ideals) for your consideration. And then you must make your choice, of the ones that speak to you particularly.

That about wraps things up. But I promised I would come clean about how I identified the Nine Defining Qualities. So here it is. I used an a posteriori method. By that I don’t mean (tempting as it may be to suggest) that they came out of my posterior. What I mean is that instead of sitting back and deciding what I thought cool meant, and then picking my people and themes, I picked first and decided later. I picked the coolest people. I picked the coolest things. Then I considered what they seemed to reveal about the meaning of the word.

None of my Idols, incidentally, possesses all Nine Defining Qualities of Cool, though most would score pretty high on The Cool Test (which you’ll find in the Appendix). There may be themes in this book that seem relevant to none of these qualities. I make no apology for that.

What I will do, though, is very briefly answer two more questions suggested by the title.

5) Is cool cool?

By this I mean: is cool a good thing? Is it desirable?

The answer to this is: yes and no. Or rather, yes and no and yes. Yes, because usage defines meaning, and cool is always used positively; it can’t refer to a negative thing. No, because its Nine Defining Qualities may encourage a certain superficiality in outlook and self-destructiveness in style. But then finally yes, because many of those qualities do seem admirable even when viewed outside the prism of a cool value system: for example, the habit of questioning authority, the impulse to live creatively and the knack of self-control.

6) Who is the coolest person ever?

There’s a story told by the Greek historian Herodotus, in which the rich King Croesus asks the wise Solon, “Who is the happiest of men?” He’s hoping that Solon will reply, “You, Croesus”, since he was so stinking rich. But Solon (an Ancient Greek version of an anti-capitalist) wasn’t having any of it. He starkly declared that the happiest of men was some guy Croesus had never heard of: an ordinary citizen named Tellus. Tellus, apparently, had lived to see all his grandchildren survive infancy. He then perished nobly in battle.

Personally, I’m with Solon up until the part about dying in battle. But he does make a good point, which is relevant to us here. The likeliest thing, of course, is that the coolest person who ever lived is someone we’ve never heard of.

All of which said, I did take the trouble to cast around and see if I could find anyone who possessed all Nine Defining Qualities of Cool. As I mentioned, none of my Idols gets full marks. Yet I did, nevertheless, identify one person who seems to have managed this remarkable feat: one who, if I’m honest, rather surprised me. It was Jesus Christ.

And with that I must leave you.

When I began writing, I threw a cigarette a long, long way up into the air. I have to stop writing now, in order to catch it in my mouth and light it.

Like so.

How to be Cool: The 150 Essential Idols, Ideals and Other Cool S*** is available from Icon Books

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