June Wilkinson was born 27 March 1940 in Eastbourne, England. Having started as a stage performer at the age of 12, she went on to become the youngest topless dancer, at the age of 15, at the Windmill Theatre in London from 1957 to 1958. During a promotional tour in the United States, she was discovered by Hugh Hefner. Her first appearance in Playboy, in September 1958, was titled "The Bosom". She was a brunette in those days, but in later shoots she was a blonde.
Wilkinson's second Playboy appearance was photographed by Russ Meyer. Meyer was an independent photographer at the time, and filming his ground-breaking The Immoral Mr. Teas (1959). Because she was under contract to Seven Arts at the time, Wilkinson could not officially appear in Meyer's film. However, as an uncredited and unpaid favor to the director, Wilkinson's breasts can be seen through a window in one scene.
Wilkinson appeared in Playboy again in August 1959 in a spread titled "The Bosom in Hollywood." During this period, she appeared with Spike Jones' band, together with actor Billy Barty. Recalling this period in her career, Wilkinson later remembered Barty with affection, but commented that off-stage, Jones had no sense of humor. In 1960, Wilkinson was featured in Playboy five times, in June, July, August, October, and again in November. Her feature in the November issue was titled "The Bosom Revisits Playboy". Wilkinson appeared in the 1960 voodoo film, Macumba Love, which promoted her measurements as "44-20-36". At times reported as up to "45-22-35", in 1963 Wilkinson stated that her measurements were actually "40-22-35".

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