Dylan dates the origins of his work as a visual artist to the early 1960s. A few drawings reached the public gaze with album covers like Music from Big Pink (1968) and Self Portrait (1970). In 1974, Dylan spent two seminal months studying art with Ashcan School tutor Norman Raeben, who philosophised the importance of 'perceptual honesty' - painting life as it as seen, not imagined. Dylan says of this time: "He put my mind and my hand and my eye together, in a way that allowed me to do consciously what I unconsciously felt."
The artist’s journeys between cities and towns are personified by his Expressionist lines, which capture the instant moment of a place, person and time. Repeated motifs encourage the viewer to explore the depths of colour and the evolution of his work. His art has been likened to that of Pablo Picasso, with critics applauding the relatability of his collections. He paints mostly from life, stating: "I’m pretty much interested in people, histories, myth, and portraits; people of all stripes."
In November 2021, the Bob Dylan: Retrospectrum exhibition opened at the Patricia & Phillip Frost Art Museum in Miami, where it ran until April 2022. Following a successful tour in Shanghai, Beijing and Shenzhen, the display spanned six decades and was the largest exhibition of Dylan's work to ever be displayed in the United States. Featuring over 180 paintings, drawings and ironworks from throughout his artistic career, it also included Dylan's brand-new Deep Focus series, which transforms scenes from films into cinematic paintings.