Stauffer’s syndrome is a paraneoplastic syndrome that has historically been associated with renal cell carcinoma. It is defined by the anicteric elevation of liver enzymes in the absence of liver metastasis, and the reversibility of clinical and biochemical changes upon treatment of the primary pathology. Here, we discuss the rare presentation of Stauffer’s syndrome in a patient with advanced metastatic prostate cancer. A 72-year-old male presented with generalized weakness, dizziness, weight loss, and icterus who was incidentally found to have a prostatic enlargement on physical examination. The laboratory investigations and radiographic imaging confirmed the diagnosis of metastatic prostatic cancer without any evidence of mechanical biliary obstruction as confirmed by biopsy and imaging. The cancer had metastasized to pelvic sidewalls, pelvic bones, ribs, urinary bladder, and local lymph nodes. Our case signifies that a high index of suspicion for underlying cancer should be maintained in patients presenting with cholestatic liver dysfunction, with or without jaundice, especially in the absence of a recognizable mechanical etiology of cholestasis.