Questions remain as to whether American artists -- who under current U.S. regulations can give concerts legally in Cuba only under the guise of a non-profit -- will be allowed to be paid directly as commercial performers. And, if that is the case, it's unclear who the promoters for such concerts might be.
The White House also announced that travelers to Cuba will be able to use U.S. credit cards there for the first time, and that new regulations will facilitate transactions between U.S. and Cuban bank accounts.
New regulations will also support the flow of information about music being made in the two countries by aiding the increase of Internet providers in Cuba, and allowing for the export of hardware and software to the island.
Obama’s move to drop Cuba from the list of terrorist states (if successful) will abolish an arduous and unpredictable visa process that has for years challenged Cuban artists wishing to enter the United States to perform, an activity that is now only allowed as a cultural exchange, with artists legally receiving only a per diem while on tour.
Before the announcement of renewed diplomatic relations, the artistic relationship between Cuba and the United States had in 2014 gone to a new level. Rent will debut on Christmas Eve in Havana, the first Broadway musical to be staged there in 50 years. The show is being produced by heavyweight promoters Nederlander Worldwide Entertainment, in partnership with the Cuban National Council of Performing Arts.
This week, Enrique Iglesias' "Bailando" which features Cubans Descemer Bueno and reggaeton group Gente De Zona, set a record of 32 weeks at No. 1 on the Hot Latin Songs chart. As Gente De Zona travel regularly back and forth between Miami and Havana, the spectacular global hit marks the first time that a song featuring Cubans who have not abandoned Cuba has been on the top of the chart.
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Bueno has lived in Miami since 2000 but is also a star in Cuba, and says he struggled for years to gain ground as an artist in this country.
"For a long time, the Latin market in the U.S. hasn’t supported Cuban artists," he told Billboard previously. "But with Enrique by our side, Gente De Zona and I broke through with 'Bailando.'"
Obama’s new Cuba policy “totally changes everything,” Pierre Hachar, an attorney who represents Gente De Zona told Billboard. “When an artist puts out a record today it’s for the world to listen to. And if it becomes a hit, a Cuban artist can be heard around the world, though they may not know the success they have because they can’t leave Cuba. And if they do leave, they’re restricted. They can perform here with a P1 visa but they can’t get paid in the U.S. That’s why a lot of Cubans go out of Cuba into Europe. They can’t flourish with a career [in Cuba] through your typical platforms of distribution. They have to do it through another country.”
Gente De Zona’s solution was to apply for U.S. residency, rather than enter the States as performers. “Now that their residency is granted, they can move forward and get paid,” Hacher explains.
Cuban music had enjoyed a boom in popularity in the United States after Washington exempted Cuban recordings and other "informational material" from the trade embargo in 1988, and later allowed Cuban artists to perform stateside, although under the condition that they receive no more than per diem payments. By 2000, hundreds of musicians from the island had performed in the States, most prominently Buena Vista Social Club, whose 1997 Ry Cooder-produced album on Nonesuch went on to sell more than 1.8 million U.S. copies, according to Nielsen SoundScan.
After 9/11, the Bush administration banned the Cuban artists. The U.S. Department of State did not authorize any such visits between 2003 and 2009. That year, Obama loosened travel restrictions for Cuban artists and other Cuban nationals. In 2013, Cuba relaxed travel restrictions for its citizens.
“I think with Cuba, for the first time what was impossible is starting to happen,” Bueno says. “I’ve been able to perform in Cuba in spite of the fact that I’ve been living in Miami since the year 2000. I’ve done it in a respectful way, I’ve just asked for what’s my right as a Cuban -- to go to my country and play for the Cuban people.”
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While it seems that now a perfect storm of artistic and political events could strengthen both Cuba’s draw as a music destination and Cuban artists’ popularity in the United States, Obama’s “new course on Cuba” will not totally take down the embargo -- that power is in the House and Senate. As well, these first stabs at diplomacy cannot instantly smooth over complicated relationships between Cubans and Cuban Americans, nor will they erase the impact of Cuba’s decades of isolation and distance from the U.S. and global music economies.
“This is still a work-in-progress,” cautions Bill Martinez, a Bay area attorney who has handled the majority of visa paperwork for Cuban artists who’ve performed in the United States and for American artists who’ve traveled to Cuba over the past two decades. “We’ll soon find out how this plays out.”
Martinez revealed he is working on events for 2015 that could be test cases for the new regulations.
"A happy day has arrived," Silvio Rodriguez, the singer-songwriter who's often called "the voice of the revolution," wrote on his blog from Havana after Raul Castro announced the talks with Obama and the release of Cuban political prisoners on Wednesday. "I vote that this attitude of dialogue continues on both sides, so that we can live in peace like the neighbors we are."
But no such elated message came from another famous Cuban artist, Gloria Estefan, who said through a spokesperson that she would have no comment on the matter at this time. Estefan made no mention of the historic news about her native land Wednesday on her Twitter account, either, only commenting that she was taping a guest spot on Glee.
It can be supposed that Estefan, a supporter of the U.S. embargo against Cuba, was not thrilled to see images of the U.S. president sitting down with one of the Castro brothers.
Pitbull, who in 2006 released a song contemplating the death of Fidel Castro, and once reportedly hinted lightly that he would run for president of Cuba; and other Miami-based artists who through the years have been outspoken critics of the Cuban regime were also silent on social media.
A Florida International University poll on Wednesday found that 68 percent of Cuban Americans supported restoring diplomatic relations with Cuba.
"This something so many people have been dreaming about," says Martinez. "I even thought it was a dream when I got the call. It's tremendous."
--Additional reporting by Leila Cobo.