In the context of American literature, John Steinbeck stands as a writer able to delve into the American psyche and study cultural changes unfettered by specific literary classifications, such as modernism and post-war texts. Although commonly known as a modernist writer, Steinbeck has evaded this literary branding and adopted a kaleidoscope of writing styles and genres to communicate his views toward American culture. This thesis tracks how Steinbeck uncovers the qualities of "the American" in almost any capacity from economic hardships to wartime and even the abundance of consumerism. The analysis begins with the comedic, celebratory treatment of the paisanos living in the Monterey hills through Tortilla Flat (1935). Steinbeck continues the glorification of social outcasts in the witty Cannery Row (1945), a text which explores the male and female gender roles within American culture specific to the 1940s era of post-war prosperity. Next, the second chapter examines Steinbeck's exploration of his own family history in East of Eden (1952) and unveils the mask of American idealism, especially in regards to marriage and domesticity, agrarian idealism, and the American Dream. The final chapter discusses Steinbeck's scathing critique of consumer culture in The Winter of Our Discontent (1961). In Steinbeck's final piece of fiction, the characters within the novel encounter the loss of morality due to a culture obsessed with material wealth and economic prosperity. This novel suggests Steinbeck's complicated opinions of American culture within his final years. By the end of this thesis, I suggest that through all of Steinbeck's various phases from the 1930s to his death in 1968, Steinbeck recognizes America's faults, yet still remains loyal to the country he spent decades examining.