The Jewish people have been more fully integrated in an American society with the decrease of anti-Semitic practices and feelings since the Second World War. However, the new flows of the Holocaust survivors into the U.S., the birth of the nation of Israel, the rapid assimilation of younger generation of Jewish Americans to American values and practices, and the negative self-image and self-hatred of Jewish people which had been formed in a long period of their diasporic experiences brought the issue of identity of Jewish Americans into sharp relief. Philip Roth was criticized from his early career as dangerous and irresponsible by Jewish audiences because his jewish characters were thought to be negatively described proving his tendency of self-hatred. Considering this context, this essay attempted to analyse his early works such as "Goodbye, Columbus,"and "Eli,the Fanatic" and to show how he strives to explore the dilemmas of the Jewish Americans of the 1950s with a realistic and balanced perspective. In these early stories, the realistic aspects ofJewish people`s lives such as the increasing differences between the successful Jewish people and those from low class,the insurmountable differences between the assimilated Jewish Americans and the Holocaust survivors were well portrayed with vivid representation of their inner desires and conflicts.