Turned westward towards profitable transatlantic trading routes, the city of Glasgow first profited from the removal of the Navigation Laws in the wake of the 1707 Act of Union before industrial shipbuilding consolidated its economy. Both its merchant and its working classes thrived on its maritime situation before bearing the brunt of deindustrialisation in the 20th century. As the latter drew to a close, art and culture were hailed as economic alternatives to the derelict shipyards. The shift from heavy industry to the creative industries is by no means one unique to Glasgow’s regenerative process launched during its bid to be named European City of Culture in 1990, but the city’s inventive conversion of derelict post-industrial spaces and early inclusion of site-specificity in public art in many ways made it a case apart and inaugurated the earliest experiments in new city governance relying on culture to transform and revive post-industrial cities. When, in 1985, David Harding was appointed head of the new Environmental Art Department at Glasgow School of Art, he promoted a new transdisciplinary approach focused on the context of the work more than on its medium or genre. In the Nineties, the figurative representations of coastal life by Alan Davie and John Bellany, and of the city’s industrial history by the New Glasgow Boys, were replaced by a site-specific approach integrating layers of recollection of glorious and then arduous times, which allowed a revisiting of a history shaped by transatlantic exchanges. This chapter explores the more liquid forms adopted by artists who have continued to work with the city’s maritime identity at the turn of the century, and the moral stance this fluidifying of form represents.