Washington Irving remains one of the most recognized American authors of the 19th century, remembered for short stories like <I>Rip van Winkle</I> and <I>The Legend of Sleepy Hollow</I>. 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 Col