For most of his life, Sittow worked as a court portrait painter, for Isabella of Castile and her Habsburg relatives in Spain and the Netherlands, and other prominent royal houses.

[2] Michael Sittow was born in 1468 or 1469 in the Hanseatic city of Reval (then part of the Livonian Confederation) to a wealthy family.

[6] At first Michael Sittow studied painting and sculpture in his father's workshop, while attending the city school to learn Latin, arithmetic and singing.

[9] Sittow collaborated with Juan de Flandes on the series of small panels of the lives of Christ and the Virgin for the queen.

In the same year, he returned to Reval, where his stepfather, the glass-maker Diderick van Katwijk, had seized his parents' houses, as Michael's mother had died in 1501.

[5][12] According to some sources, in 1514 Sittow also painted a portrait of Mary Tudor, Queen of France (now in the Vienna Kunsthistorisches Museum), the daughter of Henry VII, as part of the betrothal negotiations.

From the Netherlands, Sittow returned to Spain and worked for Ferdinand II of Aragon, followed in 1516 by the Spanish King Carlos I, the future Charles V, Holy Roman Emperor.

When Charles V abdicated from power, he took Sittow's wooden sculpture of the Virgin and three paintings with him to his retirement in the monastery of Yuste.

The name of Michael Sittow was nearly unknown for centuries, until in 1914 Max J. Friedländer put forward a hypothesis that Master Michiel, court painter of Queen Isabella, is the author of the diptych discovered near Burgos, depicting the Virgin and Child on one side and a Knight of the Order of Calatrava on the other.

[2] Sittow used translucent layers of paint to achieve highly refined and subdued color harmonies, combined with light effects and sensitivity to texture.

Though his biography is well documented, the only works that can be attributed to him with certainty are two rather atypical very small panels from a large series mostly by Juan de Flandes for Queen Isabella.

The attributions of both the portrait (today in Washington, D.C.) called Don Diego de Guevara (d. Brussels 1520, a nobleman whose family came from Santander in northern Spain; valued member of the Habsburg court in Burgundy[15]), and the painting of the Virgin and Child which together with it once formed a diptych,[16] are nearly certain, as Diego's illegitimate son Felipe de Guevara mentions his father's portrait by Sittow.

Narratives and Synergies in the Late Gothic in Castile ' by Olga Pérez Monzón and Matilde Miquel Juan mentions Sittow as one of the artists involved in creating of Retablo de Santiago, ca.

The book is written in the form of a judicial inquiry and explores such issues as nationhood, political exile and cultural assimilation.