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We report a case of a 73-year-old male with multiple, metachronous primary malignancies. He presented with adenocarcinoma of the stomach with transverse colon invasion followed by bladder cancer, hypopharyngeal cancer, urothelial cancer, and hepatocellular carcinoma, in that order, over 10 years. While these multiples malignancies were separate entities, they shared several etiologic factors, including smoking. To the best of our knowledge, this is the first description of five metachronous malignancies in a Korean patient.