Chondrosarcoma of the skull base is an uncommon neoplasm that comprises 0.15% of all intracranial tumors and 6% of skull base lesions. Compression of vital neurologic structures by tumor expansion as well as the histologic characteristics contribute to the malignant potential of these neoplasms. Tumor recurrence has been associated with incomplete resection in this traditionally surgically inaccessible region. This review of five cases of chondrosarcoma of the skull base examines the surgical approaches to resection in a chronologic fashion to emphasize that total gross resection of these lesions has become possible through the evolution of lateral skull base techniques. The difficulty in pathologic diagnosis and the efficacy of postoperative radiotherapy in enhancing survival are also addressed.