The management of complicated cholecystitis in an elderly patient can present a complex clinical decision for surgeons. There is literature supporting the use of immediate laparoscopic cholecystectomy for cases of uncomplicated cholecystitis in elderly patients and complicated cholecystitis in the general population. There are, however, no clear guidelines for treating the unique presentation of an elderly patient with complicated cholecystitis. This is likely due to the many clinical risk factors that must be considered when caring for these complex patients often with many medical comorbidities. In this report, we present the case of an 81-year-old male with complicated chronic cholecystitis leading to the exceedingly rare complication of gastric outlet obstruction. The patient was successfully treated with percutaneous cholecystostomy tube placement and interval subtotal laparoscopic cholecystectomy.