Pleomorphic adenoma is the most common type of salivary gland tumor and the most common tumor of the parotid gland. Because of its propensity for invasion, pleomorphic adenoma of the parotid requires superficial parotidectomy or total parotidectomy to minimize the risk of tumor recurrence. We report a case of pleomorphic adenoma of the parotid gland with repeated recurrences. A 23-year-old male patient presented with a protruding neck mass. Six years prior to this presentation, the patient had undergone superficial parotidectomy for the removal of pleomorphic adenoma of the right parotid gland at our institution. The patient experienced recurrence at 17 months after the initial resection, which required a total parotidectomy with partial resection of the facial nerve. Pathologic examination revealed histologic findings consistent with pleomorphic adenoma across the surgical specimen from all three of the operations. The patient suffered from facial nerve paralysis, with facial expressions partially recovered over a year.