Metastatic melanoma is renowned for its propensity to spread to almost every organ of the body; however, symptomatic metastases within the biliary tree are very rare. We report two cases of bile duct obstruction from metastatic melanoma. The first case was caused by an intraluminal metastatic melanoma to the common bile duct, while the second case was caused by extraluminal involvement. The unique aspects of these cases include clinical presentations masquerading as biliary colic, cholangitis and obstructive jaundice. Management and follow up for 3 years is presented. Aspects of medical and surgical management, as well as a review of the world's literature are discussed.