This thesis investigates the contemporary crisis of masculinity as it pertains to power, control, misogyny, violence, and multiplicities in identity. It examines the current cultural anxieties and paradoxes that circulate in popular culture with respect to what it means to be a man. Employing O.J. Simpson’s mediated representations, this work identifies and deconstructs the discourse surrounding Simpson’s fetishized male body along with his status as an American cultural male icon, a celebrated football star, and a violent murderer. By way of an analysis of diverse popular texts, in particular stand-up comedy, the thesis examines how the issue of O.J. and the issue of manhood have been broached by humour from the nineties to now, revealing the contradictory forces that constitute dominant forms of masculinity.