Artmaking has a long tradition in commercial fishing communities. In the nineteenth century, American whalers adorned their journals and logbooks with poetry and illustrations, while sailors practiced scrimshaw, carving intricate designs into shells, walrus tusks, and whalebone. More recently, since 1997, commercial fishermen from across the Pacific and Atlantic coasts have gathered annually in Astoria, Oregon to share their original poetry, storytelling, and songs. This study examines the material conditions of fishermen’s work and artmaking across these two historical periods: the peak of the American whaling industry (1840–1860) and the contemporary U.S. commercial fishing industry (2000–2025). I find that fishermen’s cultural production offers insights into the material conditions of labor in times of social, economic, political, and environmental upheaval, whether during the Industrial Revolution or today’s climate crisis. These findings suggest that nineteenth-century whalers’ art was an instrumental, enterprising, and colonizing project, whereas twenty-first-century commercial fishermen’s art serves as a form of cultural preservation, celebration, stewardship, and advocacy. By comparing these historical moments, this study contributes to sociological and historical understandings of culture-making, labor, and the environment by illustrating how the conditions of work shape artistic expression and how laborers respond to shifting social and environmental pressures through cultural production. More broadly, I propose a theory of division of labor, which argues that work and art are both co-constitutive and dialectically opposed, continuously shaping and challenging each other.