There is a wide spectrum of head and neck cartilaginous lesions which include both neoplastic and nonneoplastic processes. Cartilaginous tumors of the head and neck are uncommon, posing a diagnostic challenge. Benign cartilaginous tumors that may occur in the head and neck include chondroma, chondroblastoma, chondromyxoid fibroma, osteochondroma, and synovial chondromatosis. Chondromesenchymal hamartoma is a rare non-neoplastic cartilaginous lesion that is included for the 1first time in the new WHO classification and radiologically can mimic a tumor. Malignant cartilaginous tumors include chondrosarcoma and chondroid variant of chordoma. Characteristic tumor locations, internal chondroid matrix calcification, and typical T2 hyperintense signal secondary to high-water content within the extracellular matrix of the hyaline cartilage are useful imaging features that narrow the differential diagnosis and help in diagnosing these diseases. This article presents a narrative review of the anatomy of the head and neck cartilaginous structures, discusses the current knowledge and imaging spectrum of benign and malignant cartilaginous tumors and tumor-like lesions of the head and neck.