Objectives. To review our institution's experience and outcomes in the treatment of lateral temporal bone (LTB) and parotid malignancy with facial nerve (FN) involvement. To identify risk factors for treatment failures and to clarify previously established prognostic factors for this advanced-stage disease. Study Design. Case series with chart review. Setting. Tertiary care academic hospital. Subjects and Methods. A series of 26 patients treated operatively for malignancy of the LTB and parotid gland with FN involvement were reviewed retrospectively. All patients underwent sacrifice of the FN due to intraoperative determination of nerve invasion. Demographic, historical, intraoperative, pathologic, and follow-up data were collected and analyzed to determine survival outcomes and locoregional control. Risk factor analysis was performed. Results. The FN was found to be grossly involved by tumor at the stylomastoid foramen in 57.7% of patients, resulting in sacrifice more proximally in the vertical segment in 57.7%. Statistical analysis demonstrated a locoregional recurrence rate of 34.6%, with the majority of recurrence occurring within the first 2 years after surgery. The rate of distant failure was 15.4%. Kaplan-Meier and chi-square analysis showed an overall survival of 76.0%, 66.7%, 35.3%, 31.2%, and 28.6% at 1, 2, 3, 4, and 5 years, respectively. Advanced age, the presence of tumor of epithelial origin, and pathologically positive lymph nodes are significantly predictive of poor survival. Conclusion. Outcomes of malignancy of the LTB with FN involvement treated with primary surgical therapy compare favorably with previously published control rates, and overall prognosis for this condition is likely better than historically established.