We report a case of pleomorphic adenoma of the right parotid gland with two recurrences. A 74 year old male presented with a gradually enlarging right cheek mass for 10 years. The patient underwent excision of the mass twice. 3 years prior to consult, patient underwent excision at a local hospital and histologic findings were consistent with pleomorphic adenoma. The patient noted recurrence 4 months after the last excision, and after two years sought consult due to gradually enlarging mass on the right cheek. Fine needle aspiration biopsy done revealed pleomorphic adenoma right parotid. Facial and neck CT scan with contrast revealed a heterogenously enhancing mass with cystic and necrotic component involving the right buccal space measuring 8.8 x 8.1 cm. No osseous involvement and no enlarged cervical lymph nodes were noted. Patient underwent superficial parotidectomy with wide excision. Wound was closed primarily. Aside from minor swelling near the right zygomatic and buccal area which eventually subsided, no major post operative complications were noted. Patient was discharged stable on third day post operation.