Daddy Yankee’s career started well before the release of his 2004 breakthrough Barrio Fino. A core contributor to DJ Playero’s seminal mixtapes, the rapper from Río Piedras had dropped his debut album, No Mercy, in the mid-1990s, well before reggaetón had a name. Recording under the name Winchesta Yankee, the young Puerto Rican artist took inspiration from Jamaican dancehall, Panamanian reggae en español, and American hip-hop—and even on those early recordings, Yankee’s raw talent was evident. By the time Barrio Fino arrived, reggaetón had established a foothold not just in the Caribbean, but in places like New York City, where decades of Latin American immigration and naturalization had previously fostered the vibrancy of salsa music. An established figure with countless tracks under his belt, Yankee wasn’t the only perreo star to emerge from this new wave of Spanish-language artistry. But Barrio Fino propelled him to worldwide fame. For a period of time in the mid-2000s, in the right cities and neighborhoods worldwide, his urgently felt hit single “Gasolina” was more common than birdsong, emanating ubiquitously from stereos and automobiles. The inevitability of an album like this to emerge from the fertile, vibrant reggaetón scene of the 2000s was all but assured, especially in the wake of a broader acceptance of Latin artists that had taken hold around the turn of the century. A stark counterpoint to the bilingual pop that defined the preceding “explosion,” Barrio Fino crossed over without compromise or concession. The album is both a product of its time and ahead of the curve: The rugged beats assembled by studio teams like Monserrate & DJ Urba, as well as by the iconic Luny Tunes, were far from the glossy, accessible singles fronted by more glamorous mainstream stars. Barrio Fino was truly the sound of the streets, the anthemic refrain of “Lo Que Pasó, Pasó” set to an irresistible thump. Elsewhere on the album, songs like “King Daddy” and “El Muro” burst with the boisterous energy of New York rap, featuring dembow rhythms alongside Yankee’s unvarnished, sometimes profane lyricism. “Like You,” meanwhile, finds Yankee paying direct homage to Big Punisher, while positioning himself as an heir to the late rapper’s legacy. Though Yankee would later embrace pop music, directly aiding in reggaetón’s mass appeal worldwide by the early 2020s, Barrio Fino showcased a musician finding success on his own terms.