The relationship between a fictional character and its reader is one built on sympathy. Likable characters who combat personal adversity or who possess culturally acceptable and praised characteristics at the time of the fictional work's publication garner compassion from its audience. Does the same kind of reader reaction occur when characters of an unfavorable social status begin to transgress specified cultural attitudes to better themselves? In this paper, I examine the role of three literary characters of illegitimate birth: Mordred in Sir Malory's Le Morte d' Arthur, Edmund in William Shakespeare's King Lear and Jon Snow in George R.R. Martin's A Game of Thrones. I question how negative cultural attitudes at the time of each work's publication affect the way each character conducts himself whether as an agent of assumed social chaos or an autonomous bastard whose actions strive to transcend his undesirable birth rank. Each of these three characters represents specific types of bastards. Both Mordred and Edmund are bastard villains. Mordred's actions are pure unforgiving evil, and his destruction is self-indulgent and justified, to the audience, due to his illegitimate birth. Edmund is more complex, as he emotionally manipulates both the reader and other characters in the play, vacillating between a victimized bastard and a power hungry political player. Jon Snow is least like Mordred and Edmund. He endures the typical Renaissance era social and familial ostracism, and works to separate himself wholly from his illegitimate reputation while subconsciously seeking to prove himself worthy of legitimate respect.