This paper focuses on feudalist structure and values within this system in George R. R. Martin's fantasy novel series A Song of Ice and Fire and Shakespeare's play King Richard the Third. The paper is structured into three arguments that focus on different characters from each work. The first argument is focused on Tyrion Lannister and Richard III's deformity, and how they violate feudalist values. This argument ultimately comes to the discussion of whether or not these characters are monstrous and by what values. The second argument is focused on Daenerys Targaryen and Margaret, discussing why both authors give these women a supernatural power. The authors give women these powers because they believe that women should have power. Martin argues that women need to remake the structure, while Shakespeare believes women can change their place in the structure through collective action. The last argument focuses on Petyr Baelish and Richard III, and how they both represent a chaos attacking feudalism. Petyr is a chaos that comes outside the system, exploiting the values of the system, while Richard is a chaos within the system because he violates feudal values, while trying to hold positions where he needs to embody feudalist value. The authors come to different conclusions of what is trying to take down feudalist structure and how this could be fixed. Martin finds feudalism cannot be fixed and that other systems are not much better because they still create violence. Shakespeare comes to the conclusion that feudalism cannot be fixed because people continue to violate its values, so a new system must be put in place.