Cutaneous angiosarcoma of the face and scalp is a rare malignant vascular tumor that most often occurs in the white elderly males. No clear etiologic factors have been associated with the development of this aggressive neoplasm. Due to delay in diagnosis, inability to adequately define clinical and surgical margins, and its high local recurrence and metastatic rates, angiosarcomas generally have a poor prognosis. Histologic evaluation of angiosarcoma can be somewhat difficult due to the varying patterns of differentiation. We present a case of angiosarcoma arising on chronically sun-damaged skin and review the histopathology and prognostic factors important in this malignancy.