Squamous cell carcinoma (SCC) of the prostate is a rare tumor with aggressive nature. This type of tumor has a poor response to conventional treatment and results in poor prognosis. Squamous differentiation or metaplasia may arise subsequent to endocrine or radiation treatment, but it is very rare. To date, a few cases have been reported in the literature. Due to its rarity, the radiologic findings of SCC of the prostate are not well established. We describe a case of SCC of the prostate developing in a patient with adenocarcinoma of the prostate following hormonal therapy. Furthermore, we review the imaging features of this rare disease across multiple imaging modalities.