Painter and printmaker Roland Penrose was born in Watford in 1900, the son of a successul portrait artist, James Doyle Penrose. His mother Elizabeth was the daughter of a wealthy Quaker banker, and the Penrose children were raised in a strict Quaker household. Penrose attended Leighton Park School and then Queen's College in Camridge where he studied architecture. He soon switched to painting, moving to France upon graduation to continue his studies. There, he married the French poet Valentin Boue and became friends with Pablo Picasso, Wolfgang Paalen, and Max Ernst, who would have a lasting influence on Penrose's work.

In 1936 Penrose returned to London, settling in Hampstead and becoming a harbinger of English avant-garde society. He helped organize the London International Surrealist Exhibition, and opened the London Gallery on Cork Street where he promoted Surrealism and Abstract Expressionism. He organized a tour of Picasso's famous Guernica to raise funds for the Republican Gernment of Spain. Penrose became an ardent supporter of the artists' in the relatively new field of Surrealism, collecting many of his friends' and contemporaries' works in addition to producing his own.

On the heels of divorce in 1937, the artist and entrepreneur soon became involved with photographer Lee Miller, whom he would later marry, and with the onset of World War II both artists became active participants (despite Penrose's Quaker upbringing). Miller worked as a photojournalist, and Penrose worked first an air raid warden and then as a captain in the Royal Engineers. It has been suggested that his work as a Surrealist artist led to his expertise in camouflage, and to his commission as senior lecturer at the Easter Command Camouflage School in Norwich. During his work on behalf of the Royal Engineers, Penrose helped secure safe passage and jobs in the U.S. and England for many Europeans artists.

Following the war, he and Miller married. in 1947 Penrose and the art critic Herbert Read founded the Institute of Contemporary Arts (ICA) in London, and he helped organize the first two major exhibitions: 40 Years of Contemporary Art and 40,000 of Modern Art, which featured ancient African art and sculpture, the sort of works that helped influence and define the creative impetus of many early 20th century Abstract Expressionists and Surrealists. In 1949 Penrose and Miller aquired the Farley Farm House in East Sussex, and transformed the property into a haven of AbEx and Surrealist works. The landscaping itself was designed by Penrose to compliment his ever growing sculpture collection. The property has since become a museum and archive operated by the couple's son, Antony Penrose.

Roland Penrose was also an author, penning a number of books about the lives and work of many of his friends. He was knighted in 1966 for his service in the visual arts, and in 1980 the he was awarded an honorary Doctorate of Letters by the University of Sussex. He died in 1984.