No king has been given such exemplary status as Henry V. Much of that reputation rests on the fame of two writers’ works, neither of which coincided with his reign, but both referred to it from a distance. In the first case, Hoccleve offered the Regiment of Princes, a handbook on good governance, to the Prince of Wales, Henry of Monmonth, a rising star in the political sphere, but who was not yet king. In the second, Shakespeare explored the memory of the troubled prince who became the Legend of Agincourt and the ideal king in his play King Henry V. Both poets wrote at troubled times marked by dynastic change: royal as well as political and religious uncertainty. While their initial audiences may have differed, the first being a court poet, the second a popular playwright, the popularity of their poems went beyond their original audiences. Both works were widely published at early dates, but both (Hoccleve in particular) went into relative eclipse before returning to artistic and literary prominence. It can be safely said that both works raise questions about political responsibility that continue to resonate today. Neither knew the other. Hoccleve preceded Shakespeare by nearly two centuries, of course, but having never been published in print until much later, Shakespeare most likely had never read him, which allows us to have two distinct visions of the authority and leadership that exemplifies good governance. How have those questions evolved between the early Lancastrians and the last of the Tudors? What are the shared concerns and what had changed? The most intriguing question being the shared choice for an example of kingship: why is it that in both cases, Henry V who would stand as the model of kingship?