Metastatic spread of prostate adenocarcinoma to the temporal bone is very rare. Involvement of the jugular foramen may result in Collet-Sicard syndrome. This syndrome is characterized by paralysis of the lower four cranial nerves. A case of metastatic prostate adenocarcinoma involving the temporal bone causing Collet-Sicard syndrome is presented. This case highlights an uncommon manifestation of prostate adenocarcinoma causing symptoms referable to the occipital condyle of the temporal bone. Few cases have been reported in the literature of Collet-Sicard syndrome due to metastatic prostate cancer. This case reminds readers that awareness of atypical presentations may reduce diagnostic delay and expedite appropriate treatment.