The work of E.J. Bellocq and George Dureau although superficially distinct, share a number of core attributes: each lived and worked in the historic French Quarter (albeit separated by several decades), took portrait photographs of denizens of their neighborhood, each sought out non-traditional subjects for portraiture, e.g., sex workers, prostitutes, and people who are disabled or homeless. In each case the artist is perceived as empathetic with the subjects they depict, that the artist seems to have known the subject. Explored herein is what may account for these shared qualities. Interestingly, these artists’ works manifest two key features of New Orleans history: 1) acceptance of a sex industry and sex workers, and 2) the prominence of homosocial relationships and the overt presence of a homosexual, LGBTQ community. Moreover, Wilhelm Worringer’s approach to empathy (einfühlung in German) in Abstraction and Empathy, whereby the artistic production of a place reflects that culture’s view of the world, is exemplified by the similar qualities in each of Bellocq’s and Dureau’s artistic production. Additionally, the three core aspects of the German concept stimmung (a subjective and collective social mood, an objective and pronounced atmosphere, along with a distinct affinity for the musical) are all uniquely possessed by New Orleans, particularly in the French Quarter. To wit, the French Quarter provides a real-world archetype of Robert Sinnerbrink’s concept of enveloping mood, where the mood of the place is itself a key player in the unfolding narratives (comedic, sensual or dramatic), going on there. New Orleanian Lillian Hellman’s quote from which the name of this essay was taken, “seeing and then seeing again,” reflects her revisiting events of her life. Here, however, the ones doing the seeing are Bellocq and Dureau. First Bellocq saw, and then Dureau saw again. These men encountered the same physical and cultural milieu, and their output reflects that place.