Enrique Iglesias

The son of legendary balladeer Julio Iglesias, Enrique Iglesias eventually eclipsed his father's success thanks to a bilingual body of work which drew upon his Spanish roots while also keeping up with contemporary pop trends. A huge star on the Latin American scene from the moment he released his 1995 self-titled debut, Iglesias would eventually break the record for the most number ones on the Billboard Hot Latin Tracks chart and ended the 20th Century as the biggest-selling Spanish language artist in the world. Iglesias also perfectly timed his first foray into the English-speaking market during the Latin pop boom of 1999 with Enrique, scoring US number ones with "Bailamos" and "Be With You." But unlike many of his peers, Iglesias' mainstream popularity also continued into the new millennium, with 2001's Escape spawning his signature hit, "Hero," and reaching diamond status, while his willingness to embrace everything from R&B to EDM ensured he remained a regular on the Billboard charts throughout the following two decades.