This article examines how Oswald von Wolkenstein and Sebastian Brant use the motif of “shipwreck with spectator” (Hans Blumenberg) as a metaphor for human existence in their respective literary works. While Oswald, the late medieval poet, refers to the theological opposition of sin and grace, Brant, the early modern humanist, cites the philosophical opposition of folly and wisdom. In his songs ‚Es füegt sich‘ and ‚Wie vil ich sing und tichte‘, Oswald interprets the shipwreck he once experienced as an allegory for the troubled life of a sinner dependent on God’s help. Brant, on the other hand, suggests in his satire ‚Das Narrenschiff‘ that it is possible to autonomously escape the disaster of a foolish life by appropriating the wisdom of ancient literature and philosophy. Both authors mention in passing a wine container: For Oswald, it symbolizes God’s grace saving him from death; for Brant, it signifies a folly that leads to ruin.