Born in South Wales in 1950, Cherry Pickles gained a degree in Mathematics from Ulster University before going on to study at Slade School of Fine Art and the Chelsea School of Fine Art, London. Pickles has taught at multiple art institutions including Canterbury School of Art, Falmouth School of Art, St Andrews University and the Royal Drawing School. In addition to this, Pickles has taught drawing workshops in Italy with Gerhard Richter and Eric Fischl. Following this, Pickles was invited to take up the role of Artist in Residence at Omi in New York and, later, a Residency at Altos de Chavon in the Dominican Republic and the Guston McKim Residency in Yaddo. Pickles has exhibited her art extensively at galleries such as The Room Gallery, Chichester Art Gallery and Turps Gallery. Pickles's My Sullen Art: Self-Portrait as Dylan Thomas (2011) was acquired by Ruth Borchard Collection in 2011.
Primarily a figurative painter, Pickles's subjects are often shown in settings that dramatically contrast open and closed spaces. My Sullen Art: Self-Portrait as Dylan Thomas casts the artist as a lackadaisical male author, leaning backwards in her chair, with a cigar and a whisky, illuminated by a warm yellow background, a memento mori ominously placed on the table beside her. Of her figurative painting, Pickles has said: 'I like the challenge of painting people because images of people produce stronger responses in the viewer than any other images.'