Chios mastic gum derived from the plant Pistacia lentiscus L. variation chia has been shown to exert beneficial effects on a wide range of human disorders. The most comprehensive data so far have indicated that mastic gum provides protection against gastrointestinal malfunctions and bacterial infections. Substantial evidence has also suggested that mastic gum exhibits hepatoprotective and cardioprotective, antiinflammatory/antioxidant, and antiatherogenic properties. In the last decade, an increasing number of studies further evaluated the potential antiproliferative properties of mastic gum against several types of human neoplasia. The present review aims to summarize the current data concerning the anticancer activities of mastic gum and their major constituents, highlighting also the molecular mechanisms through which they exert anticancer function. Mastic gum constituents that belong to the chemical class of triterpenoids appear to be mainly responsible for its anticancer potential. Thus, a brief discussion is dedicated to the anticancer activity of synthetic and naturally occurring triterpenoid analogues with similar chemical structure to mastic gum constituents. Taking into consideration the available data so far, Chios mastic gum could be considered as a conglomeration of effective anticancer drugs.