Familiar to reggaetón lovers even before the genre had a name, Daddy Yankee has come a long way since spitting bars and singjaying dancehall-style on DJ Playero’s pioneering mixtapes in the 1990s. The Puerto Rican dynamo’s thumping call-and-response single “Gasolina” resonated in a major way back in 2004, giving both him and reggaetón itself a tremendous international profile. For nearly two decades now, he’s proven a pop-savvy evangelist for música urbana, collaborating widely with artists from Héctor "El Father" and Wisin & Yandel to Anuel AA and Natti Natasha, and even reaching back to his dancehall reggae roots on hits “Con Calma” and “Dura.” Alongside Luis Fonsi and Justin Bieber, he made the slinky “Despacito” a world-beating smash that shattered language barriers and ushered in a new era of Latin pop prosperity.