On the Road is a classic American novel that appeared at a time of great political, cultural, and psychiatric upheaval. Published almost 60 years ago, it still exerts great influence. We propose that the affirmative approach toward “madness” in the novel can enlighten our understanding of alternative perceptions of mental illness. The novel is analyzed with quantifying and narrative methods focusing on the concept of madness, which is a prominent theme in the novel. Stigma and glorification of madness can be found throughout the text. The positive sides and the pitfalls of an overly positive attitude toward mental illness and minority group members are discussed, including benevolent discrimination, recovery, and positive psychiatry.