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Endoscopic biliary drainage (EBD) for unresectable hepatocellular carcinoma (HCC) associated with obstructive jaundice remains controversial because of the short survival of these patients. To evaluate the effectiveness of this procedure, we retrospectively studied 18 patients who had unresectable HCC with obstructive jaundice and underwent EBD with poly-ethylene stents, over a 10-year period. Nine patients with tumor thrombus involving the first branches of the portal vein or portal trunk (Vp3) formed group A and the other 9 (Vp0–Vp2) formed group B. The serum albumin level and serum total bililubin level differed significantly between the two groups (P < 0.05 and P < 0.005, Student's t-test), but prothrombin time did not. The obstructive jaundice was mainly caused by direct tumor invasion in 6 patients from group A and 3 from group B, by blood clots and/or tumor fragments in 2 patients from group A and 3 from group B, by the tumor protruding into the common hepatic duct in 2 patients from group B, and by tumor compression of the common bile duct in 1 patient from each group. Drainage was successful in 4 patients (44%) from group A and in all 9 patients (100%) from group B. Among the 5 patients with unsuccessful drainage in group A, 4 had obstruction of both the left and right hepatic ducts and 3 had multiple tumors in both lobes. The mean survival time (mean ± SD) after EBD was 47 ± 44 days in group A and 181 ± 70 days in group B. In group A, the average survival time was only 85 days in the 4 patients with successful drainage. However, an improvement in the quality of life after EBD was observed in one-third of the Vp3 patients and in all of the Vp0–Vp2 patients. In summary, satisfactory palliation is possible with successful EBD, but this is difficult in most patients with Vp3 portal thrombus, direct tumor invasion involving both hepatic ducts, and multiple tumors in both lobes. It is important to determine the site, extent, and nature of the obstruction, as well as liver function and the presence of portal thrombus, before performing EBD.