Extrahepatic cholangiocarcinoma, including hilar cholangiocarcinoma, is a relatively rare diagnosis. However, it frequently has been associated with major problems in diagnostics and clinical management from its first comprehensive description by Klatskin up until today. In this article, cholangiocarcinoma, representing the most common biliary tumor, as well as the differential diagnoses of benign and malignant biliary obstruction, will be discussed. The latest improvements of cross-sectional imaging modalities (sonography, CT, MRI and PET) and their diagnostic values for detection and staging will be displayed. A practical imaging-based diagnostic approach to obstructive biliary disease will be proposed.