During the 1950s Charles White began a notably fertile period as an artist whose work appeared on records of the Vanguard label. Vanguard was a particularly innovative record label, founded in 1949 by Seymour Solomon and his younger brother Maynard Solomon in New York City. The label grew to become one of America's leading independent labels. Charles White supplied drawings and illustrations for a number of Vanguard records, for the most part with 10 inch sleeves. Many of these were jazz recordings, but in one or two instances his illustrations were used for other types of recordings. 

In 1954, Charles White provided an illustration for the cover of folk singer Brother John Sellers' recording Jack of Diamonds. The record was released on the Vanguard label as part of its ‎Vanguard Jazz Showcase – VRS-7022. Again, it was a 10" mono recording. The record sleeve stated "Cover drawings (sic) by Charles White.