Few artists in recent years have had Bad Bunny's impact on the music industry, popular culture, mainstream and underground aesthetics, and the economies tied to each of these realms. A remarkable anomaly by any measure, Bad Bunny's embodiment of extremity comes through in his gender-fluid style, Afro-Caribbean aesthetics, sexually explicit lyrics, and vibrant critiques of colonial politics. As a Puerto Rican colonial subject himself, he has consistently amplified the voices of oppressed groups, while also championing marginalized communities impacted by the effects of colonialism and conservatism, in Puerto Rico and elsewhere. This collection, the first comprehensive publication focused on the Bad Bunny phenomenon, puts the artist, his work, and activism into conversation with various contexts relevant to culture, society, representation, identity, and politics. Bringing together a cadre of scholars - some supporters, others detractors - the collection offers a balanced transdisciplinary look at his work and its influence on intersectional resistance struggles. Part critique, part celebration, the chapters contained within question whether his influence signifies a cultural shift or a flash in the pan. Consequently, this collection aims to understand Bad Bunny as a multifaceted signifier whose meanings evolve depending on the generational, geographical, and sociopolitical perspectives framing the enigma.