This chapter examines two versions of hedonist theories of the life worth living, one rather pessimistic, adopted by the Cyrenaics, particularly Hegesias, another more optimistic, adopted by the Epicureans. Both these approaches tend to diminish the gap between the best possible life and a life at least barely worth living, though they do so in converse directions. According to Hegesias, the best possible life falls to the level of a life just barely worth living, that is, a life in which there is no more pain than pleasure. According to the Epicureans, the threshold of a life at least barely worth living is raised to the proximity of the best possible life. A happy life, that is, a life of pleasure, must be a philosophical life, since only philosophy can guarantee freedom from disturbance. But freedom from disturbance is also required for a life worth living, so that a life is not worth living unless it is guided by philosophy, with the important caveat that a progress in philosophy, or the promise of such a progress, is sufficient for a worthwhile life.