Oncologic resections in the head and neck can result in a variety of complex defects. Many free tissue transfers have been described for soft-tissue reconstruction in this area. The pedicled, vertical gracilis myocutaneous flap has been well described for use in the perineum, but is rarely used as a free tissue transfer because of previously documented unreliability of the skin island. The objective of this study was thus to review a single author's experience with reconstruction of complex head and neck defects using the vertically oriented free myocutaneous gracilis flap. A retrospective review of all head and neck reconstructions at a major cancer center from 2003–2006 was performed. Demographic, oncologic and reconstructive data were retrieved from a prospectively maintained clinical database. Ten patients (mean age, 57 years; range, 33–84 years) with complex defects of the head and neck were reconstructed using a gracilis myocutaneous flap with a vertically oriented skin paddle. Seven patients had a malignant skin tumor; 3 patients had a parotid gland tumor. Mean surface area requirements were 88.6 cm2. Composite resections were common and included skin, facial nerve, mandibular and/or temporal bone, partial glossectomy, parotidectomy, and/or orbital exenteration. Six patients had a history of prior irradiation; 6 patients received postoperative radiotherapy. Mean follow-up was 8 months (range, 2–20 months). Total flap survival was 100%. There were no partial flap losses. Primary wound healing occurred in all cases. The vertically oriented free myocutaneous gracilis flap is a reliable option for reconstruction of moderate volume and surface area defects in the head and neck. It represents an underutilized flap that should be more commonly considered for soft-tissue reconstruction of complex defects in the head and neck.