In the history of portraiture, left cheek poses dominate. However, self-portraits favor the right cheek. Previous studies consistently report left biases for portraits of others and right biases for self-portraits; only one study has examined self-portrait pose orientation across a single artist’s corpus. The present study investigated posing biases of prolific self-portraitist Vincent van Gogh. Posing orientation in single-figure portrait ( N = 174) and self-portrait ( N = 37) paintings was coded. Unlike other artists, van Gogh was equally likely to paint himself in left and right cheek poses. Similarly, portraits of others showed no difference in left and right cheek frequencies but were distinguished by the inclusion of midline poses. These data highlight the importance of single artist cases studies when investigating portrait posing biases.