Abstract: The 1950’s and 1960’s in America are known as the Silence Era and the Rebel Era. The youth in those times can be grouped into those with neurosis and in pursuit of selfness，the “beat generation”emphasizing instinctive experiences and hipsters who rebel against the society through their queer behaviors. They share the characteristics of “madness”，while the madness each group bears is different in connotation. From a cultural perspective，this paper makes an analysis of the three groups and studies the connections and evolution of their attributes，values and destinies. Also，the author explores the cultural meaning and difference behind their madness，and the internal evolution of the concept of “madness”.

Key words: madness, ego, the beat generation, hipster