Benson was born in Lombardy, but moved to Bruges in the southern Netherlands after spending some time in Spain. He arrived in Bruges in 1518, and by the following year he had gained entry into the local guild of painters as an independent master. Benson was already a successful painter of portraits and altarpieces prior to his arrival, but in Bruges he worked for a short time in the studio of Gerard David. His paintings owe much to David’s style, but also reflect the art of his native Lombardy and the painters who worked there, such as Leonardo. Benson was enormously successful; his reputation brought him public commissions and his work was extremely sought after, fetching high prices.