With few competitors, Heracles was one of the most popular and widely revered heroes of Greco-Roman antiquity. In two treatises, Philo evokes his heroic virtue as a potential model for human emulation. In the Embassy to Gaius, the emperor’s claims to the divine honors of the hero are deflated in view of his failure adequately to have matched Heracles’ benefactions for human civilization. Philo notes that Gaius used to dress himself in theatrical costumes impersonating various gods and heroes, which, he suggests, reveals that the emperor’s likeness to divinity was merely superficial. In That Every Good Person Is Free, Heracles’ actions in the satyr-play Syleus serve as a model for the true sage who acts with freedom of soul even in a state of servitude. In the drama, despite his best efforts to disguise his true nature in order to deceive the murderous tyrant, his heroic attributes remained visible. Within these two treatises, therefore, Heracles is ostensibly celebrated as genuinely divine. This presentation will argue, however, that in both instances Philo subtly subverts the status of the hero. In the former treatise, this is evident in his Euhemeristic interpretation of the hero’s divine nature, and in the latter in his claim that the demigod’s achievements in virtue were surpassed by humans, including the Essenes and the philosophers Anaxagoras and Zeno.