The crisis Masculinity, a movement that peaked throughout the 90s and early 2000s, seeds itself during adolescent life in media and stigmas presented of what it means to be a man. After years of conditioning male stereotypes, the American Male enters the white collar work force and alas, encounters the pressures of supporting middle class consumerism. The pressure to uphold the image of a strong provider suffocates tender humanity into a distorted existence. The crisis of masculinity projected itself into a plethora of art, film, and literature that combats masculinity norms such as The Graduate (1967), and American Beauty (1999) which capture the emotional turmoil of white middle class America, driving the films protagonists to escape in order to swim against the mainstream. The Graduate, directed by Mike Nichols and written by Buck Henry and Calder Willingham, utilizes the unique cinematic style of Robert Surtees to narrate the struggles of the newly graduated Ben Braddock played by Dustin Hoffman. The plot and the cinematic elements work to create a sense of meaningless in the role of middle class white males. Ben Braddocks inner dissonance and sense of impending doom constitutes his falling for his parents friend, Mrs. Robinson, and her seduction which sparks an adulterous relationship that allows both parties to retreat from the dissatisfaction in their normal lives. Sam Mendes 1999 film, American Beauty, imitates The Graduates stylistic elements that evoke the meaningless of middle class American lives, however the protagonist, Lester Burnham played by Kevin Spacey, is in his mid-forties rather than Hoffman’s newly graduated character. Lester Burnham from American Beauty is a near representation Ben Braddock twenty years into the future, living a lifeless existence on the other side of the middle class American money mill. Sam Mendes illustrates the effects of Ben Braddock’s fear of middle class meaninglessness within Lester Burnham who is most of the way through his own middle class rat race and bears the scars of its erosion within his diminished character. This essay explores American Beauty and The Graduate in the context of psychoanalytical and feminist film theory. Though critics have noted these films are responses to the 20th century male crisis in middle class america, I would like to explore more fully the manifestation in sexual relationships that cannot possibly exist in society. Closer attention to these relationships, which are inversely structured in The Graduate and in American Beauty, reveal that there is not only a crisis in middle class white males facing consumerist ideologies of success, but also in undetected systems of sexual norms and repression meant to cast a light of guilt, and provide a ledge for feminist theory to discredit the crisis of masculinity. Assessing the dynamic of Lester Burnham’s relationships with himself, his wife, and his teenage crush in the wake of the crisis of masculinity, middle class America, and feminist critiques it is clear the effects consumerist America has on the white male as well as structural societal changes from Hoffman’s portrayal in The Graduate to Kevin Spacey in American Beauty.