Tallinn’s syndic and town council secretary Conrad Dellingshusen (1527–1603) was a remarkable and colourful personality whose legacy is noteworthy in Tallinn’s history of the latter half of the 16th century. Among other things, a large quantity of administrative documents that were written and formulated in his own hand, which have been preserved to this day in Tallinn’s town council archive, bear witness to this. Various doodles and drawings add a fascinating and intriguing nuance to this extensive written legacy. A few set themes emerge from among Dellingshusen’s doodles, for instance women, foreigners, soldiers, animals, and fantasy creatures, as well as satiric or grotesque depictions. He exceedingly rarely drew full-length figures. Generally, he drew only heads or busts. The doodles are quite small in terms of their dimensions. They only ‘come to life’ when they are greatly magnified. It is astonishing how he was able to provide his miniature drawings with a clear character and distinctiveness, and to highlight fascinating details. Doodling was an important means of self-expression for Cordt Dellingshusen. Through his drawings, he created – evidently without setting this as his objective – a surprisingly rich and diverse world that is still waiting to be thoroughly discovered.

The fool emerges from among Dellingshusen’s doodles as a fascinating motif. This man’s interest in the fool could hardly have been by chance. The fool was doubtless an intriguing, iridescent figure who at that time denoted phenomena on a very broad scale ranging from the lunatic to the atheist and the speaker of the painful truth, extending to the jovial entertainer. The fool was not only a literary or fictitious figure, rather he was actually present and existed in 16th century Tallinn, at folk celebrations, performances by itinerant actors, similarly as works of art in urban space or in the home milieu, to say nothing of the print medium, where the fool was to be found in both words and pictures. We cannot ignore the so-called lockups for fools beyond the city walls that were meant for the mentally ill. Hence, fools were in Dellingshusen’s view on a daily basis in one way or another.

Most of the fools that the syndic drew are grim-faced, even ominous. Thus, it is precisely the negative side of the fool that comes more to the fore in Dellingshusen’s view. At the same time, other doodles show Dellingshusen himself as a person with potential to become a fool, so to speak. Namely, he did not only draw fools, but also caricatural, oddly exaggerated and distorted grotesque faces. Based on these witty caricatures, which were admittedly created only for private use, it can be argued that Cordt Dellingshusen did by drawing on paper the same thing that the professional fool accomplished in public by way of his eloquence and physical dexterity in front of audiences.