From WorldwideWords.
Q From Ehud Maimon in Jerusalem: I would appreciate it if you could help me find the origin of the expression sick as a dog.
A There are several expressions of the form sick as a ..., that date from the eighteenth and nineteenth centuries. Sick as a dog is actually the oldest of them, recorded from 1705; it is probably no more than an attempt to give force to a strongly worded statement of physical unhappiness. It was attached to a dog, I would guess, because dogs often seem to have been linked to things considered unpleasant or undesirable; down the years they have had an incredibly bad press, linguistically speaking (think of dog tired, dog in the manger, dog’s breakfast, go to the dogs, dog Latin — big dictionaries have long entries about all the ways that dog has been used in a negative sense).