Double common bile duct (DCBD) is a rare congenital anomaly of the biliary system, characterized by the presence of two common bile ducts. The condition can be classified into five distinct types. Type Va DCBD is one of the rare congenital variations where both bile ducts open separately into the duodenum: one opens normally at the major duodenal papilla, and the second opens independently into the duodenum at a different site, usually proximal to the major duodenal papilla. DCBD is often associated with biliary pathologies such as cholelithiasis, choledocholithiasis, choledochal cysts, abnormal pancreaticobiliary junction (APBJ), and upper gastrointestinal malignancies. We present the case of an 83-year-old male from the United States who presented to the emergency department with right upper quadrant (RUQ) pain. Magnetic resonance cholangiopancreatography (MRCP) and endoscopic retrograde cholangiopancreatography (ERCP) revealed a type Va DCBD, complicated by cholelithiasis and acute calculous cholecystitis. The patient underwent a laparoscopic cholecystectomy, along with common bile duct stent placement for biliary drainage. This case highlights the importance of identifying atypical radiologic features indicative of rare congenital biliary anomalies such as type Va DCBD. Given the scarcity of reported cases in the literature, accurate preoperative imaging and early diagnosis of this anomaly are crucial for preventing long-term complications and guiding appropriate surgical management.