This paper seeks to show the development to Henry V's image from a legendary figure into a tragic hero. It first explores his legendary image in the anonymous chronicle play entitled The Famous Victories of Henry the Fifth, where he appears as a folk hero with his patriotic vaunting. Then this study moves to examine the image of Henry V in Shakespeare's Henry IV and Henry V, and proceeds to assert that the playwright presents this hero as an individual who has his personal ambitions for loyalty. But, despite his heroic feats, we note that Shakespeare ironises him because the letter conceals some qualms about his father's usurpation and complicity in Richard II's murder.