The advent of large-scale high-performance computing has allowed the development of machine-learning techniques in oncologic applications. Among these, there has been substantial growth in radiomics (machine-learning texture analysis of images) and artificial intelligence (which uses deep-learning techniques for “learning algorithms”); however, clinical implementation has yet to be realized at scale. To improve implementation, opportunities, mechanics, and challenges, models of imaging-enabled artificial intelligence approaches need to be understood by clinicians who make the treatment decisions. This article aims to convey the basic conceptual premises of radiomics and artificial intelligence using head and neck cancer as a use case. This educational overview focuses on approaches for head and neck oncology imaging, detailing current research efforts and challenges to implementation.