This large picture of a three-master gliding through the waves with billowing sails was created by Hans Holbein the Younger and is one of his most unusual drawings. Most of the works by him in this medium are elegant portrait studies using different-coloured chalks, made in preparation for his famous portrait paintings, above all of members of the English court. The "ship" seems to have been a working drawing he produced for a painting and which was not treated with particular care during the subsequent work process. It was roughly cut at the top on the right and left and was also torn and creased several times. But soon after it had served its purpose, people went to some lengths to preserve the sheet. It was mounted on backing paper and various lost details were carefully replaced.
Holbein's ship is populated by a wildly celebrating crowd of mercenaries and sailors. On all sides, wine tankards are being raised and emptied. One of the drinkers is already vomiting; another has his arm around a bare-bosomed camp follower. Neither the captain nor the helmsman is anywhere to be seen. Such depictions of ships follow in the tradition of the "Ship of Fools". This was the title of an extremely successful book published at the end of the fifteenth century which castigated the many ways in which people behaved foolishly. The author used a ship full of fools on the voyage to the fool's paradise of Narragonia as an allegory. Elsewhere, ships of this kind transport happy-go-lucky souls to the Land of Cockaigne. Executed with firm ink contours and an effective three-dimensional wash applied with the brush in several colours, Holbein's drawing can be understood as alluding to the symbolism of a false lifestyle. As part of the celebrations that followed Henry VIII's marriage to Anne Boleyn in 1533, Holbein created a number of murals - none of which has survived - for the Hanseatic merchants' guildhall in London on the subject of wealth and poverty. This ship depiction probably formed part of those paintings and was perhaps juxtaposed with a counterpart showing a disciplined and honourable ship's crew.