This article reviews the clinical characteristics, histology, biologic behavior, and recommended treatment for several benign and malignant lesions that may arise on the head and neck. Nevus sebaceus and congenital melanocytic nevus are two benign lesions that can present at a size of several centimeters. Surgical excision may be considered for cosmetic purposes and to reduce the small risk for the development of malignancy within each lesion. Basal and squamous cell carcinoma, lentigo maligna and lentigo maligna melanoma, dermatofibrosarcoma protuberans, and Merkel cell carcinoma are malignant lesions for which surgical excision is the recommended treatment. Local flap reconstruction may be used to address the surgical defects resulting from excision of these benign and malignant conditions.