Evaluation, staging, and treatment of skin cancers involve a multidisciplinary team, with radiology playing an integral role. Imaging evaluation of dermatologic disease that involves the head and neck is especially important due to the proximity of important structures such as nerves, bone, muscle, and lymph nodes. The authors review the pathophysiology of the most common types of skin cancer, as well as cutaneous lymphoma, and the available treatment modalities and algorithms. Emphasis is placed on pretreatment evaluation and posttreatment surveillance. In the pretreatment setting, a checklist of key radiologic features that are important in the staging of dermatologic disease is discussed, namely superficial and dermal lymphatic spread, perineural tumor invasion and spread, osseous invasion, and metastatic nodal disease. In the setting of high-risk or metastatic disease, a contrast-enhanced CT scan of the neck or a PET/CT scan is typically obtained approximately 12 weeks after treatment; imaging may be used first to detect residual or recurrent disease, metastatic nodal disease, or unexpected complications such as osteoradionecrosis. The authors highlight the radiologist's role in the care of patients with dermatologic disease, which can be more than skin deep. ©RSNA, 2024.