Hit Parade takes you back to the turn of the millennium when, for a couple of years, it seemed like a Latin pop star was topping Billboard Hot 100 every few weeks: Ricky Martin. Jennifer Lopez. Enrique Iglesias. Marc Anthony. Carlos Santana. Shakira. This wave of Latin crossover was hard-fought and a long time coming—from “La Bamba” to “Macarena,” Spanish-language hits in the 20th century had been treated like novelties by record buyers and radio programmers.

The Latin boom of 1999 changed all that—but did it go far enough? How did we get from the slick Spanglish of “Livin’ la Vida Loca” to the Spanish-first success of “Despacito” and “Mi Gente”? And how did Ritchie Valens and João Gilberto prepare America for J.Lo and Shakira triumphing at the Super Bowl?

Podcast production by Justin D. Wright.