Cartilaginous tumors can be subdivided into several categories according to the following three criteria: (1) Is the lesion benign or malignant? (2) Is the lesion a pure or impure cartilaginous tumor? (3) Is the epicenter of the lesion intraosseous, juxtacortical, or in the soft tissues? This article focuses on the four most common benign cartilaginous tumors, enchondroma, osteochondroma, chondroblastoma, and chondromyxoid fibroma, and on chondrosarcoma. It reviews the biologic and developmental considerations of each and discusses in depth the basic concepts in the radiologic diagnosis of cartilaginous tumors.