Every once in a while a studio, title or institution really gets on a roll. Look at Esquire, with its string of iconic covers in the 1960s under legendary art director George Lois, or Peter Saville’s Factory Records and Hacienda designs in the 1980s. Penguin’s early striking, type-driven book covers, with their clean orange and white colour scheme, are just as iconic.

However, from the 1960s, Penguin started featuring illustration on its covers. The cover artists the publisher used form a Who’s Who of UK illustration’s brightest stars over the past 50 years – encompassing Quentin Blake, Jan Pienkowski, John Sorrell, and contemporary figures including David Pearson and Jon Gray. It’s a far less stylised and more eclectic collection than the rigid, graphic-led designs.

A new book, Penguin by Illustrators, invites these creatives and many others to revisit their covers. It’s a fascinating, candid and often amusing insight into the ways that leading illustrators and publishers work.

In the book, Alan Aldridge confesses that he didn’t think he’d get away with including the word ‘shit’ in his “very undonkey looking donkey” cover for Jim Kirkwood’s There Must be a Pony! – “Then I thought, who the hell’s gonna read it? So kept the word in and the book sailed off into print.”

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Romek Marber devised the ‘Crime’ grid, which standardised the format of the crime titles and was so successful that it was rolled out over other titles. He admits in the book that he stars in many of his own stylised crime covers.

“Like most Penguin covers I did, this was extremely urgent; no time to do a ‘rough’ and get it approved,” explains Alan Aldridge in Penguin by Illustrators. “At this period of time, I guess around 1964, I was into incorporating hand-written elements into my designs: a sort of mini protest against what I saw as the sterility of standard typefaces.”

“It was convenient and I didn’t expect a fee. Friends were wary of appearing on a crime cover,” he writes. “Doing the crime covers was exciting and it was fun. I tried to make each picture mysterious and intriguing. I didn’t always succeed.”

David Pearson – who also created the cover for the book – paid homage to classic Penguin style for one of his covers, even returning to the ‘Crime’ grid.

He noticed “a very clear pattern: that Penguin has often turned to the humble circle in order to solve a design brief. So obvious is this trend that when it came to designing George Orwell’s Books v. Cigarettes, the revival of the big circle felt like a fitting tribute to the Penguin author” – and, of course, to the books’ classic visuals.

Penguin by Illustrators is published by the Penguin Collectors Society and costs £20. www.penguincollectorssociety.org

Romek Marber’s cover for The Night of Wenceslas. He says in the book that inspiration came from a pane of ribbed glass: “People passing by looked as if they were sliced into moving segments.”

Jon Gray worked on the covers for the Gabriel García Márquez series with Matthew Richardson. He says: “I had a very pretentious idea... that we would work on one piece of paper and send it backwards and forwards... Anyway we scrapped that. ... He emailed it to me instead and I painted the type over the top.”