Site icon Ed Callow Writing and Editing

33. The Miles Davis Quintet – Workin’



Have you noticed that things seem to be getting smaller nowadays? 

Must be a sign of the times. Take Toblerone, for example: fewer triangles of nougat-studded Swiss chocolate, more euros handed over at the airport gift shop. Whether due to health concerns, changing consumer trends, the squeeze on high street retail, or rose-tinted nostalgia, products seem to be getting more and more svelte with each passing year.

And – just like Toblerone – record liner notes are now pretty stripped back. Buy a new LP in 2020 and take a look at the back cover/inside. Here’s what you’ll find:

Probably (but not definitely) a tracklisting.

Possibly some notes naming the musicians and producers who worked on the record.

Maybe a pull-out lyrics sheet. 

Maybe even some thanks and acknowledgements. Not likely though.

What you probably won’t see anywhere is a full blown, subject-object-verb sentence. You might not even see punctuation.

And what you certainly won’t find is a long piece of writing espousing the virtues of the record and making a convincing sales argument. An essay of over 1000 words, laid out in finely crafted newspaper-style columns, designed to convince the person who has just pulled the record from a crate that they should take it up to the register and part with their hard-earned cash for a piece of cardboard and some wax containing music that they presumably haven’t even heard yet.

Essentially: you won’t find long copy anymore.

And maybe that’s understandable. 

With a huge increase in the number of radio stations playing popular music, the proliferation of digital platforms and formats, and – above all else – the internet, there’s no reason to assume that the potential customer hasn’t already heard the record they’re holding. Trends have changed too, with artwork and minimalist design taking precedence over reams of text. And perhaps there’s been a conscious move away from explicit advertising and commercialism in liner notes. Music is still big business, of course, but as the factory-line production of Motown gave way to the anti-commercialism of punk, artists may well have felt a pressure to separate their art and their marketing. (There’s a playlist of songs about advertising at the end of this post, and most of them take a stance that could be charitably described as “not exactly favourable.”)

Maybe it’s the copywriter in me, but I have to admit to a certain fondness for these old record sleeves. Sure, they’re out of fashion, but they make a great read: a relic from a bygone era of dark, smoke-filled jazz clubs and larger-than-life musicians bearing their souls up on the stage. I love the paraphernalia that comes with a physical medium like vinyl, and the more copy there is for me to devour, the better. I guess I also have a vested interest in long-reads about music.

But I also like them because, aesthetically, they remind me of something pulled straight from the pages of Ogilvy on Advertising. Those classic, classy mid-century advertisements with witty headlines and crisp, clean copy. Maybe it’s just the thick columns of black and white text, or the simple fact that long copy ads are almost as rare as long liner notes these days, but those classic ads and these LP sleeves certainly share a bit of DNA.

And that got me thinking… what would the legendary ad man David Ogilvy have to say about these sleeves?

The details

So, together, that’s what we’re going to do.

We’re going to analyse these liner notes and see what they can tell us about long copy and the ideas of David Ogilvy.

We’ll give each section a score based on Ogilvy’s advice, too.

I’ve picked out one of Miles Davis’ less well known records for this exercise: Workin’ with the Miles Davis Quintet. It features the titular Davis on trumpet and the equally legendary John Coltrane on sax (alongside a rhythm section with less star value but plenty of talent.) It’s a good record, if lacking a little polish. Essentially: plenty for a writer to work with.

The writer in question here is Jack Maher. From what I’ve been able to ascertain, he never worked as a copywriter. But he did found prestigious jazz magazine DownBeat in 1934, so he has some impressive pedigree as a music writer who knows his Miles from his Monk. 

Good: we can hold him to a high standard.

If you’d like to read the notes in full, you can expand the image above or read the plain text version available here (beware: there are a few typos). I’ll be pulling out relevant excerpts for analysis as we go along, too. 

David Ogilvy as drawn by the inimitable Jake Keane


Where else to begin, but the beginning? 

Headlines are, naturally, incredibly important.

Here’s what Ogilvy has to say:

“On the average, five times as many people read the headlines as read the body copy. It follows that unless your headlines sells your product, you have wasted 90 per cent of your money.”

In a major divergence from a classic long-copy ad, there isn’t a headline here, as such. Rather, the name of the album is given the headline slot: Workin’ with the Miles Davis Quintet.

As headlines go, it’s not bad. Lacking a bit of oomph, maybe. But Ogilvy would give it some points for including the brand name (for the purposes of this exercise, The Miles Davis Quintet is the brand being sold.) As he points out, “if you don’t [include the brand name in your headline], 80 per cent of readers (who don’t read your body copy) will never know what product you are advertising.

The word “Workin’“, too, is an interesting touch. 

The contracted verb aesthetically links this record to the quintet’s previous two releases, Cookin’ and Relaxin’. Yet semantically it’s a stark contrast. As if to say: “You’ve heard ’em relaxin’, now hear ’em workin’.” What could that sound like?

So the headline – such as it is – includes the b(r)and name, foregrounds one of the product’s main selling points (Miles Davis), and throws in a bit of intrigue. It doesn’t exactly leap off the page, but it’s passable. And since it’s not really an ad headline, we  shouldn’t be too harsh.

Ogilvy score: 3/5

The copy: size matters

Well, right out of the gate, Ogilvy would give this a big thumbs up for length.

In a section about why all copywriters should learn to ply their trade by writing direct mail, he writes: 

“In their magazine advertisements, general advertisers use short copy, but the direct response people invariably use long copy. Who, do you suppose, is more likely to be right?”

So at some 1400 words, the length of this piece certainly hits the long copy mark. 

Why is that important? Ogilvy, again:

“I believe, without any research to support me, that advertisements with long copy convey the impression that you have something important to say, whether people read the copy or not.”

This statement probably rings true for all of these older records with extensive liner notes. But that impression is altogether more important for “minor” albums like this one than for the ‘classics’. 

“Look,” it seems to say, “look at all of the things there are to be said about this record that you hadn’t even heard of before.”

Done right, long copy simultaneously tells you that you should care as well as why you should care.

Long copy rules.

Ogilvy score: 5/5

The copy: layout and typography

So, having established that plenty of copy is a good idea, and armed with a headline that opens fairly strongly, we’re faced with a new issue: space.

We have a 12″ by 12″ square to work with… not exactly huge. There’s a certain amount of information that needs to be included, too: the musicians, the tracklist, the address of the label. These things may be optional nowadays, but leaving them out back in 1960 would have been inconceivable. 

So how can we also find space for nearly 1500 words of copy?

Naturally, David Ogilvy has some ideas. I’ve pulled out a few that apply most directly to our example.

The eye is a creature of habit. People are accustomed to reading books, magazines and newspapers in lower case.
– All our body text is set in sentence case. ✓

Limit your opening paragraph to a maximum of 11 words.
– We’re straight in with a full paragraph. X

Widows – short lines [rather than squared paragraphs] – increase readership.
– We’re on the money here. ✓

If you use leading between paragraphs, you increase readership by an average of 12 per cent.
– Spot on here, too. ✓

Sans serif in page-size sheets repels readership as wax paper repels water; it has a sleazy, cloudy look.
– After the title, not a serif in sight. X

2 points off for a few long paragraphs and a sans serif font? Harsh, but we’re judging by Ogilvy’s standards, not ours.

Ogilvy score: 3/5

The copy: first impressions

Now that we’ve made sure that the long copy can be read, the next step is to determine whether anyone is actually likely to read it. Ogilvy’s warning is as follows: 

I must warn you that if you want your long copy to be read you had better write it well. In particular, your first paragraph should be a grabber. You won’t hold many readers if you begin with a mushy statement of the obvious like this one in an ad for a vacation resort: ‘Going on vacation is a pleasure to which everyone looks forward.’

In essence, that first paragraph – and the opening line most of all – needs to grab the reader by the scruff of the neck and shout ‘READ ME.’

Following on from that exceptionally milquetoast example, Ogilvy continues:

A Harvard professor used to begin his series of lectures with a sentence that took his students by the throat: ‘Cesare Borgia murdered his brother in law for the love of his sister, who was the mistress of their father  the Pope.’

So that’s our theory. What about practice?

Our potential customer is standing in a record store, holding this sleeve in their hands. They’ve read the record title and know who the performers are. They’ve seen that there’s a long read ahead for them, if they want it. The first sentence may well be the thing that determines whether or not they decide to read the whole text.

What’s Maher’s opening gambit?

Miles Davis is the most maligned and idolized musician in modern American jazz today.


It certainly grabbed my attention, anyway. There’s an oxymoron at play here which immediately introduces some tension. Presumably the reader already knows that Davis is widely worshipped… but maligned? It’s a tantalising line that leaves the reader wanting more. Why is Davis “maligned”? Is it justified? (More on this later.)

One thing that I think this line does very well is in the placement of “maligned”: front and centre. Had Maher led with “idolized”, readers may have quit mid-sentence, feeling he was telling them something they already knew.

Purely from a copy perspective, I’d trim down the end of the sentence (“modern” and “today” feel a little tautological) and try to add a little more punch to the dramatic contradiction. In classic copywriter style, I’d also exaggerate the claim a little more:

“Miles Davis is at once the most maligned and idolised musician in jazz history.”

But details, details. A damn good start.

Ogilvy score: 4/5

The copy: positioning and the “big idea”

We have our readers’ attention. Good. Better not disappoint them.

So let’s return to the basics. What are we selling? 

Despite the draw of its star performers, Workin’ presents a particular challenge from a copywriting perspective.

On paper, you may think that selling a record featuring Miles Davis AND John Coltrane would be easier than a walk in the park while eating a slice of cake. And there are certainly plenty of hardcore jazz cats who would pick this up on the strength of those names alone.

But it’s not a timeless classic like Davis’ Sketches of Spain, Kind of Blue, or Bitches Brew, or Coltrane’s Blue Train or A Love Supreme. It’s not even the most acclaimed record released by the Miles Davis Quintet: a podium place reserved for Relaxin’. These records almost sell themselves, even amongst a non-expert audience. 

Workin’ is a different beast. Less polished, less ostentatious, and with fewer outbursts of visionary genius from its two visionary geniuses. So how to sell this to an audience (outside of the hardcore jazz fans) who could pass this up and instead pick up one of those better known records?

This is a problem that Ogilvy would solve through “positioning” – one of the key ideas underpinning all good advertising to this day. What traits about this product will be most effective when brought to the foreground? What will grab and hold the attention of our target audience?

And it is in the positioning that Maher appears to have had what Ogilvy would call a “big idea.

Remember that opening line? The implied criticism of the record’s star? 

What if we sold a record featuring Miles Davis and John Coltrane… by attacking Miles Davis’ legacy? By recounting a time that John Coltrane played badly? By focusing on the less famous trio behind them?

This is bold. 

But then the biggest ideas always are, aren’t they?

Almost the entire first half of the copy is dedicated to addressing – and doing nothing to dispell – a number of criticisms of Miles Davis. Having opened the piece by calling him the most maligned musician in jazz, Maher goes right ahead and maligns him some more. He is called “contemptuous of his audience”, “a poor showman […] lackadaisical and unconcerned about his playing.” Maher makes digs at Davis’ celebrity status. And, most damningly of all, writes: “Miles has been given a mystic halo by his fanatic admirers, for them he can do no wrong. Each note is a secret that they share with him alone. But these secrets are more imagined than real.”


And this is all backed up the story of one of the quintet’s gigs that Maher attended sometime in the mid-fifties. Davis was “uninterested”. Coltrane was having an off-night, his fingers seeming “full of kinks.” five paragraphs in to our copy, and Maher is sat in front of a warm beer, deeply dissatisfied.

But hang on. This is the Miles Davis Quintet. Miles Davis, the visionary. Miles Davis, the black unicorn. Miles fucking Davis. Surely his genius, at work alongside John Coltrane’s, is the main selling point here? Aren’t you meant to be selling me a Miles Davis record here?

And that’s what makes this such an exceptional feat of positioning. 

There is, I think, a slightly perverse sense of propriety in the heart of every music lover. A will to have heard of an artist before our friends, to know all of the “deep cuts,” to “prefer their early work.” When an artist becomes universally beloved for their unquestionable genius, there’s something in all of us that feels a touch disappointed, somehow. When everyone knows how wonderful an artist is, some of their appeal is lost. We may even start to consider them overrated. It’s not a nice tendency in us, but it’s there all the same.

So consider how dissatisfying and ineffective it would have been if Maher had taken the easy route here. If he had simply churned out a few tired lines about the undisputed genius of Miles Davis and left it at that. It’s received wisdom. It’s something that everyone knows. It’s boring. And as Ogilvy tells us:

You cannot bore people into buying your product. You can only interest them into buying it.

Instead, Maher tells us all of the worst things about Miles Davis as a musician, all but ignores John Coltrane, and instead heaps praise onto the players in the rhythm section. In his story, they rescue the gig when Davis and Coltrane walk off stage. And that’s interesting

As well as giving the reader the surprising delight of finding criticism where they might expect blanket praise, it gives them a wonderful piece of ‘conversational ammo.’ When their friends and peers talk about the genius of Davis or Coltrane, they can nod knowingly and say “of course, the real geniuses were on bass, piano, and drums.” 

They’re back in on the secret.

Ultimately, this long piece of copy positions the record as something other than the listener might expect. A record that challenges some of their presumptions about jazz. A piece of something different. 

Personally, by the time Maher starts talking about the tracks on the LP, I’m already sold.

Ogilvy score: 5/5

Beyond Ogilvy: the “so what?” test

So we’ve put the text to the Ogilvy test, and it’s fared pretty well.

But, of course, the godfather of advertising isn’t the only person with something to say about copywriting. Far from it, in fact.

As one final assessment of these liner notes as a piece of long-copy, let’s subject the piece to the “so what?” test. 

This is a classic exercise which could certainly do with being applied more widely in the internet age. Take your premise, your headline, and your body copy, and ask yourself one question: “so what?”

As David Ogilvy was fond of doing, let’s start with a bad example. Just this morning, I received an email newsletter from a company announcing “exciting news.” Great! A special offer, perhaps? A new, groundbreaking product that will revolutionise the way I live my life?


Turns out they have a new CFO.

Well… so what?

Turns out exciting news isn’t that exciting for everyone. The appointment of a new chief financial officer will have almost no material impact on me, the potential customer. I’m left feeling disappointed and bored. It’s a bit of copy that does not pass the “so what?” test.

But what about our piece? What is it saying?

“This is an album by the Miles Davis quintet, featuring John Coltrane.”

So what?

“Davis and Coltrane are actually the least interesting elements here, and this record is good to listen to almost in spite of them, and because of the unfairly lesser known rhythm section.”

Now THIS I have to hear.

So what? test passed, with flying colours.

Final score: 4/5

So sure, long copy might be a little out of vogue in a lot of fields. But, done smartly, just look at what it can achieve. 

Advertisers, creative directors, sleeve designers, record labels, I urge you:

Give us some space for long copy. We’ll repay the favour with some big ideas.


Copy that.

  1. So What? – Miles Davis
  2. Advert – Blur
  3. Commercial – The Jesus and Mary Chain
  4. TV Ads – Paranoid Visions
  5. Natural’s Not In It – Gang of Four
  6. The Commercial – Wire
  7. California Commercial – Ty Segall
  8. Commercial Alternative – Teenage Fanclub
  9. The Agency Group – Alvvays
  10. Koka Kola – The Clash
  11. Sports – Viagra Boys
  12. Soap Commercial – The Psychedelic Furs
  13. Headline Hustler – 10CC
  14. (I Can’t Get No) Satisfaction – The Rolling Stones
  15. Advertising – The Dip
  16. Radio Commercial – The Sugarhill Gang
  17. A Commercial – Dead Kennedys
  18. Gary Gilmore’s Eyes – The Adverts
  19. Eat Yourself Fitter – The Fall
  20. Public Image – Public Image Ltd.
  21. She Sells – Roxy Music
  22. Holy Shit – Father John Misty
  23. It’s Alright, Ma (I’m Only Bleeding) – Bob Dylan
  24. False Advertising – Bright Eyes
  25. 1000 Words (Spoken Word version) – Scroobius Pip

My own liner notes:

All quotations from:

Workin’ liner notes (Originally published 1960 on Prestige Records. Notes by Jack Maher.)

Ogilvy on Advertising (Originally published 1983 by Crown Publishers)

You can find Jake Keane at and his DIY punk zine Creative Rehab.

Exit mobile version