Hemorrhagic cholecystitis is a rare diagnosis that closely mimics acute cholecystitis. Physical examination, laboratory studies and, in particular, computed tomography imaging allow for rapid diagnosis, stabilization and emergent surgical intervention. We describe our experience with three patients requiring emergent surgical intervention for hemorrhagic cholecystitis with unique clinical features including decreased platelet function due to liver cirrhosis, dual antiplatelet therapy and intraoperative finding of cholecystohepatic communication. Furthermore, we provide video recordings of two cases highlighting the severity of the disease. All presented patients were hemodynamically unstable and showed peritoneal signs on exam. Laboratory studies revealed moderate anemia and leukocytosis, while computed tomography suggested hemorrhage in the gallbladder. All patients required blood transfusions during their care and underwent laparoscopic cholecystectomy. Hemoperitoneum and gallbladder perforation were confirmed intraoperatively. Patients fully recovered without significant postoperative complications due to expedited operative management.