Distal malignant biliary obstruction is caused by various malignant diseases that require biliary drainage. In patients with operable situations, preoperative biliary drainage is required to control jaundice and cholangitis until surgery. In view of tract seeding, endoscopic biliary drainage is the first choice. Since neoadjuvant therapies are being developed, the time to surgery is increasing, especially in pancreatic cancer cases. Therefore, it requires long stent patency. Recently, preoperative biliary drainage using self-expandable metal stents has been reported as a useful modality to secure long stent patency. In patients with unresectable distal malignant biliary obstruction, self-expandable metal stent is the first choice for maintaining long stent patency. Although there are many comparison studies between a covered and an uncovered self-expandable metal stent, their use is still controversial. Recently, endoscopic ultrasound-guided biliary drainage has been performed as an alternative treatment. The clinical success and stent patency are favorable. We should take into consideration that both endoscopic retrograde cholangiopancreatography-guided biliary drainage and endoscopic ultrasound-guided biliary drainage have advantages and disadvantages and chose the drainage method depending on the patient’s situation or the expertise of the endoscopist. Here, we discuss the current status of endoscopic biliary drainage in patients with distal malignant biliary obstruction.