Hemorrhagic cholecystitis is a rare cause of abdominal pain that can present in the setting of trauma, malignancy, and bleeding diathesis, such as renal failure, cirrhosis, and anticoagulation. Its symptoms are easily confused with acute calculous cholecystitis and might include hemobilia or hematemesis as blood drains from the gallbladder into the gastrointestinal tract. Imaging of hemorrhagic cholecystitis can be misleading unless the possibility of this diagnosis is considered. In this report, we present 2 cases of hemorrhagic cholecystitis along with relevant imaging and a review of the literature on this rare subject.