In December of 2002, The Roots arrived in Havana to play a free show at Casa de la Musica. “The whole street was filled with people,” recalls Edgaro Gonzalez whose band Doble Filo opened for the US hip-hop act. “The whole block was locked down but the organizers couldn’t handle all of the people at the door so they finally opened them and just let everybody in.”

The show was majestic and culminated with a syncopated ballad for the lovelorn titled “You Got Me.” That night, however, Erykah Badu’s part was sung by none other than Res, whose talents have tragically flown under the mainstream radar. Still, Edgaro and his friends knew exactly who she was when she hit the stage and purred to the mic. There were fists in the air as screaming fans sang along. “Everybody knew the songs, even the Cuban government officials that were there,” he says. Cuba and the audiences that welcomed The Roots so warmly made a deep impression on one person in particular: their drummer Questlove, who promised himself he would one day return.

The relationship between Cuban and US hip-hop cannot be understated. At this point in the game, Havana can easily be regarded as the Bronx’s scrappy little brother. These family bonds were established in the early nineties when young Cubans with homemade antennas fused themselves to the sounds of pirated radio signals coming out of Miami. At the same time, the economic hardship created by Cuba’s Special Period was the perfect backdrop for Yankee rhymes about fighting institutionalized adversity to resonate with neighboring disenfranchised communities across the water. Alliances have been formalized and compacted by organizations like The Black August Collective, who brought US hip-hop artists to Cuba on several occasions starting in 1998. There was also the first ever Hip-Hop Unity Concert in 2003 at New York’s famed Apollo Theater, where Doble Filo had the opportunity to share the stage once again with The Roots. Most recently, the ease of travel restrictions and rumors of a forthcoming lift to the decades long embargo has put Cuba front and center for culture and music heads such as Questlove, who jumped at the chance to play a DJ set at Havana’s Fabrica de Arte Cubana.

The short, Okayplayer-produced documentary Quest for Cuba tracks his visit in February of this year. We follow Questlove as he reminisces about that unforgettable concert a decade ago and returns to the Teatro America where it all took place. Doble Filo’s Edgaro acts as guide, translator and music consultant, particularly during Quest’s crate digging excursion for choice Cuban vinyl. Quest’s visit concludes with a trip through EGREM studios, whose roster of recorded artists reads like a weeklong best-of playlist.

Edgaro of Doble Filo

For Edgaro, Questlove’s return is a symbol of bigger things to come. It could perhaps even signal the resurgence of Cuba as a musical cornucopia onto the world stage, a status that was unmistakable prior to the revolution and whose influence across the Americas was undeniable. “Hopefully more US artists will go to the island and more Cuban artists will become mainstream in the States, like in the case of Gente de Zona,” he says. “Cuban music will slowly get back its spot in the market.”

The ease of restrictions also provides locals wider access to new cultures and expressions, and allows musicians to find new inspirations that will ultimately be reflected in the music. With the world at their fingertips, Cubans have the opportunity to both elevate what is natively Cuban and borrow from all over the globe. As Edgaro puts it, “With the arrival of free internet, people will be able to mutate their sound but also give a higher value to their roots, to el Changui, el Son, el feelin.”