Parastomal hernias (PSHs) are a common complication following stoma placement. The presence of the gallbladder within a PSH is a rare and unusual occurrence, posing a significant management challenge for surgeons once encountered. We conducted a systematic review of the literature to evaluate the management and outcomes of parastomal gallbladder herniations. A comprehensive search was performed across the PubMed, Embase, and Medline databases using the search terms “gallbladder” AND “parastomal hernia.” Additionally, a reference check of the results was conducted to identify further case reports. Eighteen case reports were included in the review. The mean age of the reported cases was 77.2 years, with a female predominance of 88.9% (n = 16). Seventy-seven percent (n = 14) of patients had an original ileal stoma or conduit. The average duration from stoma placement to clinical presentation was 5.8 years and abdominal pain was the most common presenting complaint. CT imaging was the most frequently utilised modality for successful diagnosis, with only two herniations identified during surgical exploration. Notably, 66.6% (n = 12) of patients experienced associated gallbladder complications, including cholecystitis, torsion, incarceration, and even perforation, all of which necessitated cholecystectomy. Cholecystic parastomal herniation is a rare phenomenon that should be considered in differential diagnoses for similar presentations. Currently, no standardized classification or management approach exists. Based on our findings, we propose classifying gallbladder herniations into two categories: simple (without inflammatory sequelae) and complicated (with cholecystitis, gallbladder torsion, incarceration, or perforation). Simple herniations may be managed electively with intraoperative reduction of the gallbladder. In contrast, complicated herniations presenting during acute admissions require emergency surgical intervention, involving a combined cholecystectomy and PSH repair.