This thesis is a comparative analysis of four counter-cultural novels, as well as a comparison between the counter-culture in the 1950’s and the 1990’s. In my thesis I have analyzed why and how the main character in each novel has opposed mainstream society. Later I have compared the two books from the 1950’s with each other, and repeated this process for the two books from the 1990’s to find individual differences as well as patterns that might represent issues common for young people of that time period. In my conclusion I have compared the two time periods, asked why most counter-cultural movements ultimately failed and discussed their legacy for mainstream American culture. Here I have found that counter-cultural behavior in the 1990’s is not only similar to that of the 1950’s, but also that as the movement of the 1950’s failed to have any lasting impact on capitalism and consumerism, but was rather co-opted by mainstream society, this movement failed to solve many of the problems that the next generation inherited in the 1990’s.