The Wit’s Guide to Cool

Or, try not to be a repeater pencil

Oct 09, 2025

*Geoff Dyer based a whole chapter of But Beautiful on this 1958 photo by Dennis Stock*.

The coolest person who ever lived was Lester Young. To a clinical eye, specifically that of an army psychologist, his coolness presented as a “constitutional psychopathic state manifested by drug addiction (marijuana, barbiturates), chronic alcoholism and nomadism. A purely disciplinary problem. Jazz.” But then, as Young observed in a different context, “All the physicians come to hear the musicians.”

“I’ve always lived by this golden rule
Whatever happens don’t blow your cool.”
— Oscar Brown

I owe this finding to Joel Dinerstein, a clever cultural scholar who’s made a conclusive and compelling case for Young across many books and essays. How cool was Lester Young?
So cool he played the saxophone sideways.
So cool he introduced Jack Kerouac to marijuana.
So cool he wore sunglasses indoors — in 1938!
So cool that when he was insulted, he would produce a small whisk broom from his pocket and brush off his shoulder. This was more than a half century before Jay-Z’s Dirt Off Your Shoulder or Barack Obama mimed the motion in the 2008 primaries.

“He was as cool as an undertaker at a hanging.”
— H.L. Mencken

You can be cool by fitting into classic archetypes of cool, or you can be cool by being wholly original. Lester Young was both; he made the mould. In Young’s words: “In my mind, the way I play, I try not to be a repeater pencil, you dig?” The word cool predated Young; according to slangologist emeritus Jonathon Green, it can be found in American English as early as 1884 meaning “dispassionate, emotionally withdrawn, and as such a negative.” But then “its use as a term of approbation gives it some claim to be the first example of Black bad=good slang forms.” Young made cool cool. He was, as Geoff Dyer put it, “the man who learned to whisper on the tenor when everyone wanted to shout.”

“The world belongs to the enthusiast who keeps cool.”
— William McFee

Young made up his own dialect, with cool being one of the reigning adjectives. “He could say things that would really hit home,” the guitarist John Collins recalled, as recorded in Bill Crow’s Jazz Anecdotes. “They weren’t very intellectual, but he had mother wit. No one could express himself like Lester.” (Would you believe I’ve been browsing this subject for a decade and this is the first time I’ve seen the term mother wit? Can’t stop won’t stop!)

“Keep cool: it will be all one a hundred years hence.”
— Ralph Waldo Emerson

A brief Lester Young glossary, care of pianist Sadik Hakim: The police were “Bob Crosbys.” If he liked something, he had big eyes for it. If he didn’t like it, he had no eyes for it, or worse, it was a “von Hangman.” The bridge of a tune was a “George Washington.” His old girlfriends were “waybacks.” And most tellingly, when he was being discriminated against, he’d murmur, “I feel a draft.”

“Love with your mouth shut, help without breaking your ass or publicizing it: keep cool, but care.”
— Thomas Pynchon

And of course, this is why Lester Young had to be cool, and why Miles Davis’ 1957 album Birth of the Cool has the most apt name ever chosen for a work of art (A distant second: Jean-Pierre Jeunet’s tedious 2004 film A Very Long Engagement): It was a “stylistic defiance against racism,” Dinerstein writes. The slang, the sunglasses, the drugs, the disengagement all added up to a way to be in the world on your own terms. That is, to be cool.

“I play it cool
And dig all jive
That’s the reason
I stay alive.

My motto,
As I live and learn,
Is:
Dig and be Dug
In return.”
— Langston Hughes

“Whatever kind of work you do, it’s always cooler to be on deadline.”
— Terry McDonnell

It might be argued that a bit of cool, in every sense of the word, would go a long way towards fixing the world’s problems. And next week?

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If you send me money for this newsletter, I’ll send you gifts in the mail! That included Riposte Cards, the glorious collection of 28 bespoke works of art commissioned over two years, and now Aphoristicks, a monthly snicker of a sticker going out to those of you kind enough to cover the postage. The first one:

And also this:

Perhaps I can sum up Issue No. 339 of Get Wit Quick with this sticker from Arcane Bullshit: “Help! I listened to jazz and now Everything Is Jazz! (especially jazz).” Lester Young’s perfect response to gossip about his sexuality: “If you want to speak like that, what the fuck? I give a fuck what you do, what he do, what he does, what nobody do? It’s nobody’s business.” I buried all the swears down here! This newsletter’s mascot is a magpie named Magnus after the magician in Robertson Davies’ Deptford Trilogy. The title font is Vulf Sans, the official typeface of the band Vulfpeck. The book was Elements of Wit: Mastering The Art of Being Interesting. It’s profoundly uncool to ask you to tap the ❤️ below; I’ll leave it be and hope you have big eyes for it. 👀