Giant cell tumors of the head and neck are rare. We describe the case of a 50-year-old man who presented with otalgia and eustachian tube dysfunction. After his symptoms persisted despite aggressive medical management, further investigation revealed the presence of a firmness in his left parotid tail. Computed tomography identified a heterogeneously enhancing mass in the left masticator space. The tumor was removed surgically, and it was diagnosed on histopathology as a giant cell tumor. The patient recovered uneventfully and was closely followed for signs of recurrence. To the best of our knowledge, ours is the first reported case of a giant cell tumor in the masticator space. We review the literature on giant cell tumors of the head and neck, with particular attention given to cases involving the temporomandibular joint.