We report two cases of neurosyphilis with atypical clinical presentations that were compounded by atypical neuroimaging findings. In the first case, MRI brain scan findings were felt to be compatible with mesial temporal sclerosis or herpes simplex encephalitis. The second patient presented with a clinical picture compatible with normal pressure hydrocephalus as well as some degree of ventricular enlargement and prominent periventricular white matter changes by MRI brain scan. He actually underwent ventriculo-peritoneal shunting prior to determination that he had active syphilitic involvement of the central nervous system. Neurosyphilis, "the great imitator," is not only capable of mimicking various other neurological disease clinical presentations, it can also mimic neuroimaging features of various other disease processes as well.