The main aim of this diploma thesis is to provide a comprehensive, in-depth literary analysis and interpretation of a selected number of songs by Simon and Garfunkel and by Paul Simon as solo artist. Literary analyses of song lyrics are comparatively rare and tend to be underrated in their critical value. Therefore, one of the main goals of this thesis is to draw attention to the richness of content that can be found in the song lyrics of Paul Simon and Simon and Garfunkel. Hence, the main focus of this thesis lies on the literary analysis and interpretation of five representative songs: “The Sound of Silence”, “Mrs. Robinson”, “The Boxer”, “Bridge Over Troubled Water” and “You can call me Al”. In order to supply information on context and background, two biographical chapters about Paul Simon and Simon and Garfunkel are provided at the beginning of this thesis. In the critical analysis, each song is dealt with in a separate section. Furthermore, each individual song analysis is preceded by a chapter on the specific historical background, the impact and a short discussion of the music and structure of the song. This part is provided to facilitate the analysis and understanding of the songs. The actual analysis deals with each songs meaning, message and possible interpretations. Each verse and chorus (if one exists) or refrain is discussed separately. Different possible meanings and interpretations are examined in order to find the most plausible ones. In conclusion, this thesis demonstrates the multi-layered meanings and messages (politics, society etc.) of these lyrics. Furthermore, the findings of this thesis reveal aspects and details that are crucial for a comprehensive understanding of the songs.