After working in New York City in the early 1950s for John Hermansader and Esquire magazine, Miles was hired in his own right around 1955 by Francis Wolff of the jazz record label Blue Note to design album covers when the label began releasing their recordings on 12" LPs. Miles designed over five hundred covers, frequently incorporating the session photographs of Francis Wolff and, later, his own photographs, although many of his later designs dispensed entirely with photographs.
Miles wasn't particularly interested in jazz, professing to have much more of an interest in classical music; he received several copies of each Blue Note album he designed but gave most of them to friends or sold them to used record shops. Miles used the descriptions of the sessions relayed to him by producer Alfred Lion to create the artwork.
Lion's retirement as a record producer in 1967 coincided with the end of Miles' connection with Blue Note. "Fifty Bucks an album...they loved it, thought it was modern, they thought it went with the music...one or two colors to work with at that time and some outrageous graphics!".
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