Samuel Langhorne Clemens’s (Mark Twain’s) classic novels The Adventures of Tom Sawyer (1876) and Adventures of Huckleberry Finn (1884) are essential reading for every student of American literature. They continue to be of eminent significance for the discussion of the nation’s cultural heritage and make for a rewarding comparative exploration. We will discuss the novels in the context of Twain’s work and of American realism, exploring their innovative aesthetic strategies, controversial treatment of racism, portrait of Southern society, reflection of morality, and depiction of the strained relationship between individual freedom and social obligation. To this end we will not only read the novels themselves but also a variety of secondary sources that display the variety of approaches scholars have taken to the texts.