By the mid-seventeenth century, theatrical prodigals had become beloved of their audiences. In spite – or perhaps because – of the rigorous, didactic condemnations of youthful rebellion and over-expenditure that dominated morality drama, and which remained the subject of countless sermons and tracts, the prodigal archetype emerged as one of the most cherished romantic heroes of the Jacobean stage. Prodigals were in turn rakish, sympathetic, confident, cocky, and more often than not in love with women rather beyond their station, and their schemes for winning love and money (often not in that order) breathed life into dozens of dramatic intrigues. From 1500 to 1650, the prodigal metamorphosed from a criminal to be condemned or a victim of his own naivety into a flawed hero.

This shift was not, as some scholars have suggested, entirely the result of a unidirectional shift in theatregoers’ tastes. The prodigals that litter the late Elizabethan and Jacobean stages are a hearty mix of haughty rapscallions and lovable underdogs. Although the ratio is increasingly weighted towards sympathetic prodigals, didactic representations neither disappeared nor existed exclusive of their celebratory counterparts. In many plays, it remains uncertain if the prodigals depicted within should be damned or celebrated. Is Bassanio's prodigality and Antonio's nigh-fatal support of it a condemnation of exploitative Shylockian usurers or of these characters’ inability to spend within their means? Is the triumphant conclusion to The London Prodigal a celebration of the community's ability to tame prodigal excess, or a parody of such naivety? Does Eastward Ho depict Quicksilver's abandonment of prodigality in favour of industry, or his manipulation of an outdated generation who fail to comprehend the irrelevance of their own moralistic frugality?

At the heart of many of these plays are the sexual intrigues that make these prodigals sympathetic characters worth rooting for. The prominence of sexuality among works about financial excess is not a coincidence, nor solely the result of the general popularity of this theme in early modern drama (or culture in general). In dramatic works, the main ways in which this perversity emerges is in the characterisation of sex work, illicit sexuality, mistresses and syphilis.