A reconsideration of The Marriage of Alexander and Roxanne, completed ca. 1518 by Giovanni Antonio Bazzi (il Sodoma) for the bedroom of Agostino Chigi (1466–1520) at the Villa Farnesina (Rome), reveals a new understanding of the fresco as a means for promoting the banker-patron’s nobility and legitimacy. The inclusion of a grand, four-poster bed in the final composition expresses the patron’s hopes for legitimate heirs, an objective realized soon after Chigi’s marriage in 1519 to his longtime mistress, Francesca Ordeaschi. Information garnered from an inventory of the sumptuous villa, taken in 1520 after the deaths of both Chigi and Ordeaschi, allows us to hypothesize how the room was seen and used by the couple and their visitors, further contextualizing the multivalent messages that this space, and the objects it contained, may have expressed to its original audience.