From the 1820s to the 1840s, one of the most recognisable figures in Edinburgh was the eccentric John Sheriff, generally known as Dr Syntax. He was a talented amateur artist, whose work provides a fascinating and strange insight into the mind of a troubled man and, because of his interest in medicine, into the history of medicine in Scotland at the time. This paper seeks to show that Sheriff and his pictures deserve to be remembered, since they offer intriguing insights for anyone interested in the history of medicine and of Edinburgh at the end of its Golden Age.