'Mister Tambourine Man' was produced while Sharp was living in London and working as an illustrator for the underground magazine Oz. The image appeared on the cover of the seventh issue of the satirical journal, one of the most visually exciting publications of its time. Sharp also designed posters for musicians and bands, including Donovan, Cream and Jimmy Hendrix.

Sharp's image draws on the lyrics of the song by the subject of the poster, Bob Dylan. This image of the singer is synonymous with an emerging spirit of the 1960s. Emphasising youth culture’s emphasis on change and experimentation, Dylan’s lyrics have been widely interpreted as recounting his early experiences with LSD. Experimentation with LSD and other psychedelic drugs became a major component of 1960s counterculture, influencing philosophy, art, music and styles of dress. As one commentator noted, 'Sharp's living colour interpretation of LSD provided an instant in to psychedelia'.

This complex, multi-stencil design is printed on gold foil paper, and features spiralling circular motifs which radiate from the singer's head. Sharp has related 'Mister Tambourine Man' and other images from this period to his experience visiting the ancient Cambodian temple complex of Angkor in 1966. There he witnessed majestic fig trees sprout from the multitude of smiling faces which grace the towers at the Bayon temple of Angkor Thom.