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Nicolas Poussin's two Self-Portraits, painted in 1649 and 1650, have been the subject of countless art-historical investigations, but remain only incompletely understood. This study attempts to draw the meanings of the self-images into clearer focus. To this end, the relationships between Poussin and the eventual recipients of the two portraits, Jean Pointel and Paul Freart, Sieur de Chantelou, are examined more probingly and are positioned centrally in the analysis of the works. A careful exploration of the web of associations among the three men reveals that Poussin's caution in dealing with Chantelou, his often jealous and emotional patron, was a factor of great consequence to the development of the Self-Portraits. Bearing this in mind, both Poussin's letters and the scholarly accounts which accept his written statements at face value, may be approached with a more critical eye. This practice, in turn, leads to a broadened range of possibilities for the interpretation of the two Self-Portraits, and to a greater appreciation of the extent to which Poussin's creations were affected by human dynamics.