Three decades after he was able to score a senior-citizen discount at the movies, Puerto Plata (born José Cobles in 1923) will make his musical debut. But having his first CD—not to mention first Chicago appearance—at 84 years old isn’t the only thing that sets this Dominican singer and guitarist apart.

The music of his country—with Haiti its western twin on the island—is well known today for bachata and merengue, but Puerto Plata’s fingers preserve the memory of several earlier styles. Son, waltzes, boleros, guarachas and Mexican rancheras mixed together freely in the early 20th century of Cobles’s youth. “All the Cuban, Puerto Rican and Mexican composers were in communication with each other,” Cobles says through a translator. “That’s why the rhythms are very similar in nature.” Before politics intervened, it was the music Cobles still plays so well that Dominicans celebrated.

Speaking on the phone from his home in Colorado, where he has lived since immigrating to the United States 12 years ago, Cobles is far from bitter over the backward arc of his career. He listens to modern bachateros like Antony Santos (“extremely versatile and sings with a great group”), his grandchildren are in college in the States and he finally got his green card last May. “Now I’m a black white man!” he says with a laugh.

Cobles’s nickname Puerto Plata is actually the name of the coastal town where he was born. “Once I left home, I went to work for the United Fruit Company in Panama as a carpenter,” he explains. “But because everyone is from different towns and no one knows each other’s name, it was kind of a way of teasing each other. People from Santiago would be Santiagueros—I wasn’t any different.” After saving 20 pesos in a shoe box, Cobles bought a guitar and began performing at cabarets, where brothel culture and demanding schedules went hand in hand. “We would start late at night and go all the way until dawn, three to four sets a night,” Cobles recalls. “In that time, people didn’t play old bachata because [Dominican president Rafael] Trujillo said it was the ‘music of crazy people,’?” Cobles says in disbelief.

The brutal dictatorship of Trujillo, which lasted from 1930 to 1961, made cultural expression a politically dangerous choice. He championed the music he liked—orchestral and accordion merengue—and banned the music he didn’t, such as the rural guitar merengue Cobles mastered. “It was horrible living in this era,” Cobles says. “There weren’t any studios where we could record, so I had to earn a living from doing serenades all the time,” he says of the now-mythologized art of singing at the request of individuals throughout the city.

Today, thanks to the success of projects like Buena Vista Social Club, that golden era of Caribbean music has found curiosity seekers the world over. And in a cross-generational sign of respect, Pablo Rosario, one of the premier session guitarists of glossy, modern bachata, will accompany Cobles for this tour on steel-string requinto, or lead guitar.

As connected as Cobles is to his past, he isn’t marooned in cultural isolation, and is often dismayed by the resilience of totalitarianism. Right next to vintage guarachas about lost love on his debut, Mujer de Cabaret (IASO), comes “Los Piratas,” a furious merengue whose sweetness belies its warning of the pirates, or terrorists, in the Middle East. “As I lived under a dictatorship, I know that Saddam Hussein was a dictator,” Cobles explains of his inspiration.

This debut couldn’t come at a better time. “I’ll tell you one thing: The only way you mature as a singer is with age,” Cobles says. “I’ve listened to things I did when I was young and there’s no question my voice has gotten better over time.”

By: Matthew Lurie