The Athenians of the classical period were deeply invested in creating the proper conditions to produce exemplary democratic citizens and leaders out of the city’s youth. In this context, they placed immense scrutiny on the leisure practices of elite young men. Games, gambling, and hunting all raised concerns. Yet the Demos, despite its control over both public and private life, did not ban these practices. Leisure, it would seem, had something to offer youths that the State did not wish to go without. This thesis examines the fine balance between the arguments for and against these leisure pursuits, showing that, for all the negative rhetoric, they played an important role in instilling virtue and socialising young men into the ideology and institutions of the State. Games, gambling, and cockfighting were criticised for aggravating a young man’s reckless tendencies. Yet each of these practices were also valued for enculturating youths into many of the ideological cornerstones of the city. Cockfighting instilled them with a martial spirit, gambling with dice familiarised them with the powers of fortune and fate, and boardgames taught fundamental military strategy and a knowledge of kairos in battle. The second half of the thesis investigates the concerns and benefits accrued to hunting. The hunters of myth demonstrated a worrying rejection of social obligations, whilst the prevalent use of nets presented hunters as figures of suspicion and prone to cowardice. However, the hunt was also proudly defended as initiation and training in all facets of war, whilst also providing benefits to the community.