A throng of people swarm Usher, yelling his name. This happens to him every day—the only thing that changes is the location. Today, it's happening in Cuba.

Trailed by flashing camera bulbs and the crowd’s screams, he maneuvers through the ragged streets of Regla, a poor community a short ferry ride from Havana, with his entourage. His own songs play faintly from a blue portable JBL speaker carried by a member of the team. Grace Miguel, Usher’s wife and former manager, says it’s just a thing they like to do: blast music from a portable speaker, even when going out to a restaurant. It’s famous person behavior—a little like marrying your manager. The time is 7:00 p.m. on this warm April day, and Usher’s making a surprise appearance at a block party in the neighborhood.

Two of Usher’s thick-armed, bald-headed bodyguards clear a path towards a dusty lot sandwiched between multi-story houses. Dozens more fans—kids, teenagers, and older folks—have discovered he’s here too. Some are scaling trees and perching in the branches; others are standing on the roofs of their houses. Everyone is screaming too loudly to make out any of their words.


Usher, clad in all-white except for his gray Yeezy 350 Boosts, is serene amid the commotion. It’s his second time in Cuba; last time he came for his wedding. This visit, however, has a political agenda; Usher is part of a 33-person cultural delegation sent on the heels of the U.S. lifting travel and trade embargoes this past March. Grabbing a mic, he addresses the country. “Hola, Cuba!” he half talks, half sings. He then launches into his Young Thug-assisted single "No Limit"—the first from his new album Hard II Love—followed by a parade of his classic hits.

“That made me feel like a kid again,” Usher says later. “When I was a kid, we got in a cipher and battled each other lyrically. We told jokes and made the hottest dance moves. That’s what’s still here.”