We report two similar thoracoabdominal complications we encountered due to retained gallstones after cholecystectomy. These patients had had an open cholecystectomy after a failed laparoscopic attempt, with spillage of gallbladder debris intraoperatively. They were admitted more than 12 months later with subdiaphragmatic abscesses. Attempted computerized axial tomography (CT) guided drainage of these abscesses resulted in these patients developing pleural fluid collections, which required surgical drainage. The patients underwent exploratory laparotomies, and drainage of the subdiaphragmatic abscesses had revealed gallstones within the abscess cavity. A detailed presentation of these cases, with review of current literature and clinicopathologic issues for discussion are described.