American literature of the nineteenth century provided an abundance of literary icons. Ralph Waldo Emerson, the leader of the Transcendentalist movement, and novelist and satirist Mark Twain are undoubtedly among the most prominent representatives of the period. Both Emerson and Twain tried to portray what it really meant to be an American, and the unique identity they shaped in their texts has remained in American national consciousness to this day. Seemingly different –Emerson being a transcendentalist and Twain being a realist –the two authors shared similar principles regarding the position of an individual in society. The Transcendentalists put focus on non-conformity and self-reliance, i.e. they emphasized the primacy of the individual over the collective and the national.Mark Twain’s texts delivered the same message, though with a pinch of irony. In his novel The Adventures of Huckleberry Finn (1884)Twain used Emerson’s transcendentalist concepts as a framework in shaping the micro universe of the main character, a thirteen-year-old orphan, Huckleberry Finn. Even though his protagonist in many ways demonstrates Emerson’s concept of self-reliance, which is one the foundations of the American Dream, Twain also challenged this concept by showing its shortcomings. He introduced the character of a runaway slave to demonstrate that self-reliance can be achieved only in ideal conditions and that not everyone has the same rights when it comes to fulfilling the American Dream. This paper attempts to reveal both the merits and the downsides of the concept of self-reliance through a comparative reading of Emerson and Twain, as well as through an analysis of different types of characters from Twain’s The Adventures of Huckleberry Finn. Its main aim is to juxtapose the two authors’ view on the question: Can a man be both self-reliant and a part of society, or is social isolation a prerequisite for self-reliance?