This essay examines Washington Irving’s short story “Rip Van Winkle” from an autobiographical perspective by focusing on the commonality and resemblance between the author and his fictional hero. It suggests that Rip and Irving have many similar traits which underline the deeply personal and subjective dimension of the tale. It begins by considering some of these traits such as idleness, generosity and kind-heartedness. It claims that both Rip and Irving are characterized by their benevolence and altruism which account for their belovedness. After discussing these attributes, the essay focuses on other common characteristics such as the tendency to pull away from matrimony. In this matter, both Irving and Rip’s possible homosexuality are considered. Although there is no clear evidence that they are homosexuals, this essay suggests that they both seem to have a repulsive attitude towards heterosexuality. The essay then concludes by examining some of the shared views and perspectives between the writer and his character. It suggests that both Irving and Rip are characterized by their aversion to politics and by their deep love of nature. Due to the numerous and striking resemblances between the fictional hero and his creator, this essay argues that Rip is a reflection of Irving’s character and personality.