Enrique Iglesias

There was no bigger star in Latin music in the first part of the 21st century than Enrique Iglesias. He scored his first number one on Billboard's Latin charts in 1995, but he soared to crossover stardom at the dawn of the new millennium thanks to the crossover hits "Bailamos" (1999) and "Hero" (2001), a pair of blockbusters that established his ease with modern dance and classic pop balladry, respectively. Although he'd see the pop Top Ten again -- "I Like It," his 2010 duet with Pitbull, went to number four -- he was an institution in Latin music, racking up over 25 number one singles on Billboard's Latin Songs chart, along with 14 number one hits on Billboard's Dance chart, all while selling over 140 million albums worldwide in just over the first two decades of his career.