How we represent animals both reflects our attitudes towards them and affects our treatment of them. The donkey has lived alongside humans, bearing their burdens since the time of their domestication over 10,000 years ago. Despite this, they have invariably enjoyed a low status in human cultures, received little appreciation and been treated harshly. We view some animals as being more worthy than others and represent them accordingly: donkeys have been ridiculed and derided. Literary representations of donkeys from the fables of Ancient Greece to contemporary iconic texts are explored to follow the donkey through the human imaginary. These representations derive from two main, conflicting sources, Greek literature and the Bible. Examining these cultural representations may lead towards a greater understanding of the way they affect the actual animal and lead to a greater understanding of that animal and, ultimately, to better treatment of them.