Michel Sittow was born in Reval c. 1469, today the Estonian capital city of Tallinn. Possibly trained in the workshop of Hans Memling in Bruges, he subsequently moved to work in the Iberian Peninsula, where he first held the position of court painter. This monograph undertakes research on this phase of his career. In the Kingdom of Castille, Michel Sittow was appointed painter to Queen Isabella and became a member of her household with an impressive annual salary. Thanks to the analysis of archival documents and formal and iconographical studies on Sittow’s paintings, it is possible to explain the court painter’s life circumstances and describe the benefits he enjoyed and the difficulties he faced. The Castilian period was crucial for Michel Sittow’s career since over the course of his professional life, he also resided at the courts of Philip the Fair, Margaret of Austria, Christian II of Denmark and Charles V, all relatives of his first royal patron. While serving European monarchs, he transferred Memling’s techniques and visual language beyond the Low Countries and developed his artistic practice and style. The analysis of the various contexts Michel Sittow worked in sheds light on his oeuvre and his possible privileged status as a courtier, which provided opportunities to establish a flourishing and ambitious career in northern and southern Europe.