The aim of my comparative study is to examine how the nature of the picaresque contributed to the success of the two novels. How both Twain and Salinger could make the best of the possibilities provided by this literary genre. The first chapter of this thesis will offer a general overview of the nature of the picaresque. In my opinion when studying a piece of literature it is very important to investigate the historical background and the period in which it was written. Therefore, I will examine the historical, social and economic background of both Twain’s era and Salinger’s era. Still in the first chapter, I will study the general characteristic features of the picaro through the specific examples provided by Huck Finn and Holden Caulfield. I will demonstrate how the structure of the picaresque served the authors’ purposes and what functions the journey itself provides. The second chapter contains a detailed comparison of the characterization of Huck Finn and Holden Caulfield. The third chapter will focus on the recurring themes of loneliness and the journeys as the means of searching for an adult model to follow. I will follow the heroes’ journeys in order to compare how they try to make contacts with different members of society and how they relate to challenges, and to the obstacles they have to face in order to find their places in life. In the last chapter, I will examine the novels as social satires, and make comments on the style and the language of the books.