Cholesterol granuloma and cholesteatoma are the two most common destructive lesions of the petrous apex. Arachnoid cyst is less common. These three expansile lesions are often indistinguishable on clinical grounds. Cholesterol granulomas can be treated effectively through internal drainage into the mastoid cavity or middle ear. Cholesteatomas, however, are managed by more aggressive and complicated removal, which often mandates the sacrifice of hearing. Symptomatic arachnoid cysts are amenable to simple surgical drainage. Therefore, accurate preoperative recognition on computed tomography (CT) and magnetic resonance imaging (MRI) is important in planning proper treatment. Thirteen cases of destructive lesions of the petrous apex are analyzed. The authors' experience illustrates that the "typical" CT and MRI radiographic features are diagnostic in some cases, but not in all. In this study the pathologic findings have been correlated with the radiologic features on both MRI and CT.