From his street-savvy beginnings to his eventual rise to urban pop stardom, this Puerto Rican rapper has always maintained an edgy appeal. His early trap singles played with themes both criminally minded and romantically astute, making him a perfect fit for Rick Ross’ Maybach Music. The unfortunate timing of his incarceration left him sidelined during the global growth of música urbana into the mainstream, yet the surprise arrival and subsequent success of his Real Hasta la Muerte demonstrated he had only begun to show off his range. From there, he made himself known on collaborations as seemingly disparate as 6ix9ine’s “BEBE,” Meek Mill’s “Uptown Vibes,” and “Ella Quiere Beber” with Romeo Santos. He showed a softer side on “Me Gusta” with Shakira and “Culpables” with KAROL G, proving his broader pop appeal. By the time his sophomore album Emmanuel dropped in 2020, with diverse features like Enrique Iglesias on the breezy ballad “Fútbol y Rumba” and J Balvin and Ozuna on the energetic dancehall throwback “China,” he had leveled up in a major way.