This essay is an appropriation of Hans Blumenberg's work "Shipwreck with Spectator," by establishing parallels between the metaphor of shipwreck and the experiences of artistic practices and those related to academic research in the arts. In the first part of the essay, "The great sailor who always shipwrecks," I start from the theme "what remains for the castaway," the title of the second chapter of Blumenberg's book, to discuss, in general, the adventures and misadventures of the artist/researcher facing the risks of failure, in an allegory to the maritime odysseys of universal literature. The second section of the essay, "now submerged in electromagnetic waves," is more applied to the research that I, in particular, have been developing in my doctorate: the use of so-called "artificial intelligence" technologies for the creation of generative art works through cybernetic interaction between human and machine. In this chapter, I use references from pop culture, notably works of science fiction that introduce the element of AI in contemporary heroic narratives.