In the palliative setting, the necessity of biliary drainage of both liver lobes for malignant hilar biliary obstruction remains controversial. However, bilateral biliary drainage is a reasonable option to prevent cholangitis of the undrained lobe and to preserve liver function during the course of chemotherapy. Bilateral biliary drainage can be accomplished by the percutaneous or endoscopic placement of multiple self-expandable metallic stents (SEMS). Although SEMS placement via bilateral (multiple) percutaneous routes is technically simple, multiple percutaneous transhepatic biliary drainage (PTBD) may lead to additional morbidity. SEMS placement via a single percutaneous route is a useful method; however, negotiation of a guidewire into the contralateral bile duct is occasionally impossible if the hilar angle between the right hepatic duct and left hepatic duct is acute. Percutaneous dual SEMS placement is generally performed using the stent-in-stent technique (T configuration or Y configuration) or the side-by-side technique. In addition, the crisscross technique has been reported as being a useful method for trisegmental drainage. The side-to-end technique is also useful for multiple SEMS placement. In the future, the combination of percutaneous intervention and endoscopic ultrasonography-guided procedures may be effective in the management of malignant hilar biliary obstruction.