Skin malignancies are commonly encountered as primary or incidental findings. Neoplasms that affect the skin include primary (basal cell carcinoma, squamous cell carcinoma, melanoma, and Merkel cell carcinoma) and secondary (mesenchymal neoplasms, lymphoma, and metastases) tumors. Imaging provides valuable anatomic information (tumor size, depth of involvement, presence of distant metastasis, and data for guiding biopsy) and functional information (metabolic activity and sentinel node mapping data). This information, in addition to biopsy results, improves the histopathologic characterization of tumors and treatment planning. Various histopathologic types of the same entity exhibit different biologic behavior and have different imaging features. Familiarity with the multimodality imaging features, histopathologic characteristics, and various modes of dissemination (direct invasion; perineural, lymphatic, and hematogenous spread) of the most common skin malignancies helps radiologists narrow the differential diagnosis in clinical practice. ©RSNA, 2023 Supplemental material is available for this article. Quiz questions for this article are available through the Online Learning Center.