Among the many authors active during the Spanish Golden Age, Juan Ruiz de Alarcón stands out for his appearance and American background. When Juan Ruiz de Alarcón arrived in Spain for a second time in 1614 he soon became aware of the uses of theater and developed his future as a playwright. Critics have long studied how Alarcón portrays himself in the various characters in his theater. This study builds on these interpretations and claims that some of these characters are best understood as part of a strategy of self-fashioning on behalf of Alarcón: the playwright engages in self-representation in his theater as a strategy to move upward in society and make himself known in Madrid. This study uses monster studies to address the monstrosity behind Alarcón, not so much for his appearance but for the monstrosities that surround him. Furthermore, it uses the approaches suggested by scholars of the Hispanic Baroque as well as transatlantic studies to address the implications of his American background. Bringing together these different approaches, this study will show that Alarcón used his ascribed monstrosity and his networking in Mexico as strategies to compete with his contemporaries and fashion a persona that would allow his success in Madrid. Alarcón’s response to his monstrosity is observed in the paratexts of his two volumes of theater where he exposes the monstrous in his readership. He also evokes his nautical experiences when he compares his comedias to ships that navigate the theaters of Madrid. In two plays, El desdichado en fingir and Todo es ventura, the monstrosities found in Madrid are related to views of poetry and the political environment Alarcón encountered in Madrid. As an emerging playwright, Alarcón exposes deficiencies in the metropolitan center and in doing so in a subtle and comic manner, he brings attention to himself. His birth and upbringing are particularly relevant in El semejante a sí mismo and La industria y la suerte, where Alarcón caracterizes the Indies not as a source of wealth, as it was constantly portrayed in literature at the time, but as a place of unattainable wealth. This contrast makes Alarcón stand out when compared to his contemporaries, but also allows him to emulate Lope de Vega in his description of the Mexican drainage system as a Wonder of the World. America becomes one of Alarcón’s tools for upward mobility. His affinity for enclosed spaces and magic is addressed in two plays, La cueva de Salamanca and La prueba de las promesas where both comedias also evince a preocupation with the rivalry between art and nature. In both instances, Alarcón favors art over nature or the ability of outward appearances to influence reality. Lastly, I address Alarcón’s affinity for games in his two most famous plays, Las paredes oyen and La verdad sospechosa. Both comedias have a character that is new to court and seeks advice. The situation of the characters allows the plays to be interpreted as court manuals. In these guides of courtly behavior, the use of a ludic language instructs the spectator, or the reader, that approaching life as a game leads to success. The use of ludic lexicon also fashions Alarcón as an emerging playwright when compared to Lope de Vega because he self-fashions as a poet that values innovation and originality more than his contemporary.