This paper examines how Tennessee Williams shows male characters in the South during the 1950s troubled with the absurdities of American masculinity and the conservatism of the family ideology through the play Cat on a Hot Tin Roof. As a homosexual who was excluded from society his whole life, Williams resisted the confinements of masculinity and projected his antagonism through his plays as an attempt to deconstruct binary gender roles of men and women. Brick Pollitt in Cat on a Hot Tin Roof, a latent homosexual, is homophobic. Brick’s fear of social prejudice drives his friend Skipper to suicide. At the same time, his unacceptable masculinity makes him flee into enervation and refuse any relationship with his wife Maggie. His strict and absolute father, Big Daddy, embodies the consummate patriarch, but Big Daddy’s expected death from cancer depicts a price for hypocrisy, repression of family members, and misogyny, or a sacrifice for his performance as a strong man. In addition, Brick and Big Daddy’s changed character and happy ending in the Hollywood film version of this play show the difficulty of homosexuality and its inevitable compromise with the society. Based on this paper’s examination of the play’s male characters, Cat on a Hot Tin Roof can be interpreted as the writer’s social critique of American masculinity in the South during the 1950s, questioning concepts of masculinity itself, describing the gender role as no more than a masquerade forced by the society.