In light of the recent revival of interest for philosophy as a way of life, Cynicism has received relatively little attention. Classical cynicism, however, is a particularly rich and valuable school in this respect, offering a philosophy that is before anything else a way of life, combining philosophical reflection, a value system, and a practice of living. The present article articulates classical Cynicism as a philosophy as a way of life along these lines. Additionally, classical Cynicism offers a valuable contribution both to current philosophical investigation and to philosophy’s contribution to the question of the good life. In particular, classical Cynicism gives a number of guidelines for a new cynicism, distinct from and regularly in opposition to common modern cynicism.