While many surviving paintings have been attributed, there is very little known of him from records, and he tended not to sign his work. He is believed to be responsible for mainly religious art, but also painted portraits on commission. He sometime painted from classical sources, often setting the figures in modern-dress, or a contemporary domestic setting. In his lifetime he was successful; he had a large workshop, his work was sold internationally and he was especially popular in Spain.
Benson became popular as a source for pastiche with 19th century painters, who are sometimes known as the 'followers of Benson'. In particular his many variations of the Magdalen and Sibilla Persica, were further copied and became popular with contemporary buyers. Many have retained their relative value and held in the National Gallery, London and command high prices at Sotheby's.
Death of Lucretia, date unknown. The rape that lead to Lucretia's suicide can be seen in the background. Benson's treatment is unusual for history painting in the contemporary dress of the figures and then familiar interior setting.
Typical of the itinerant manner of many painters of the time, he moved to Bruges c 151and served his apprenticeship with the Early Netherlandish painter Gerard David . He later became a naturalized citizen of Bruges. Benson worked as a journeyman before he was made master in 151and became a member of the guild of painters and saddlemakers. He eventually became a dean and then and governor of the guild. He married Anna Ghyselin, and had two sons with her, both of whom became painters. He later remarried and had a daughter Anna. He is believed to have had at least two other daughters from extra-marital affairs.
Benson came into dispute with Gerard around 1519, over a number of paintings and drawings Benson had created -including a book of studies for heads and nudes as well as various patterns- in the older master's workshop without his assistance. David refused to return the material, and after Benson pursued him legally, served time in prison for his appropriation.
He served as head of the Guild of Saint Luke from 1537–153and 1543-1544. Much of his work was at one time attributed to a Spanish artist known only as the Master of Segovia; it is now believed they were the same person.
Perhaps under the influence of Rogier van der Weyden's 15th century The Magdalen Reading, Benson was one of the first artists to popularise images of women reading. It became a motif for him, and he painted the scene many times in his images of Mary Magdalen and the Sybil Persica, whom he treated as almost interchangeable.