Washington Irving remains one of the most recognized American authors of the nineteenth century, remembered for short stories like Rip van Winkle and The Legend of Sleepy Hollow. He also accomplished other writing feats, including penning George Washington's biography and other life stories. Throughout his life, Irving was at odds with socially-approved ways of being a man. Irving purportedly saw himself and was seen by others as feminine, shy, and non-confrontational. Likely related to this, he chose to engage with other men's fortunes and adventures by writing, defining his male identity vicariously, through masculine archetypes both fictional and non-fictional. Sitting at the intersection of literary studies and masculinity studies, this reading reconstructs Irving's life-long struggle to somehow win a place among other men. Readers will recognize masculine themes in his tales from the Spanish period, his western adventures, as well as in historical biographies of Columbus, Mahomet, and Washington. In many writings by Irving, especially The Legend of Sleepy Hallow, readers will observe themes dominated by masculinity. The book is the first of its kind to encompass and examine Irving's writings.