This dissertation focuses primarily on the Impressionist artist Gustave Caillebotte's paintings of rowers on the Yerres River outside Paris, created in the late 1870s. The works engage with many of the radical shifts in social and cultural norms that took place during the latter half of the nineteenth-century as industrialization and urbanization increasingly affected daily life in Europe and America. The paintings are in dialogue with developments in the fine arts, including the growing influence of Impressionism and avant-garde artists, and deal extensively with the male figure, reacting to and engaging with changing norms of masculinity. To fully examine the works, I focus on five areas of comparison. First, in considering the possible implications of changing masculine ideals in relation to the physical body during the period, I consider Caillebotte's controversial nude male bathers. I then contrast Caillebotte's oarsmen with both the professional rowers portrayed by his American contemporary Thomas Eakins, and the more leisurely boating scenes of his fellow Impressionists. Finally, I examine the history of the dandy/flâneurs figure, arguing that Caillebotte's rowers illustrate the artist's attempt to reinvent and modernize the concept. My thesis attempts to bridge different methodological approaches that have tended to isolate aspects of the artist's work, thereby obscuring his overall project of engaging with both the social and theoretical concept of modernity. Although the artist is underrepresented in the general literature of Impressionism, he has lately played a significant role in texts examining Impressionist interest in the suburban vacation spots along the Seine River. Such authors have illuminated Caillebotte's background as a serious sportsman, an aspect of the artist previously underexplored. I also build on feminist and queer theorists, who in recent years have called attention to the potential for sexual subversity within Caillebotte's oeuvre. Although acknowledging a debt to all of these scholars, my dissertation is an attempt to expand the scholarly conversation by examining how these works explore the concept of modernity, both formally, in the manner in which Caillebotte calls attention to the artifice of painting and socially, in how he engages with the changing physical landscape and the increasing potential for leisure activities outside Paris following the Franco-Prussian War. Finally, in arguing that Caillebotte rowers are transported flâneurs, who, though now engaged in daytime paddling rather than evening strolling, continue their mission of anonymity and observation, I suggest an expansion of the very definition of flâneurs, and by extension, the dandy figure that remains relevant as a type even today. / Art History