Juan Formell of Los Van Van

Cuban musician Juan Formell, leader of the Van Van musical group, speaks during a press conference on November 14, 2013 in Havana

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Before President Obama's announcement Wednesday that the U.S. would be restoring diplomatic relations with Cuba, there were five decades of a rocky musical relationship that displayed artistic triumphs, personal tragedies and the diplomatic power of music. See our timeline below:

1959
-Radio Rebelde goes on the air less than two months after Fidel Castro takes power, following former President Fulgencio Batista's flight to Miami.

What the U.S.-Cuba Breakthrough Could Mean for Music

1960
-President John F. Kennedy mandates the end of exports except food and medicine from Cuba to the United States. In 1962, this is expanded to include almost all imports.

-Celia Cruz leaves Cuba for a tour with the group La Sonora Matancera in Mexico, never to return. In 1961, she debuts as a soloist in New York at the Palladium ballroom. She later takes up residence in New Jersey with her husband, Pedro Knight.

-Future salsa singer Willy Chirino is among some 14,000 children to arrive in the United States via Operation Peter Pan, which transported kids into exile, where they were placed into foster homes until their parents could get out of Cuba and claim them. He would later criticize the Castro regime in song.

Muted Hurrahs for Easing of Cuban Sanctions

1961
-Fidel Castro and Che Guevara found the Instituto Superior de Arte to provide free education in music, dance, drama and visual art. The campus on the former site of the Havana country club was conceived as a showcase for Utopian architecture that represented revolutionary ideals.

-Cuba's first independent record label, Panart, is taken over by Cuban government officials, who seize a wealth of master recordings by artists including Bebo Valdes, Nat King Cole and Celia Cruz. Ramon Sabat, who founded the label in 1942, goes into exile with his family. Before leaving, they smuggle out their own copies of the masters. RCA Victor and other majors also leave the country.

-Citing government attempts to intervene in her career, the Queen of Bolero Olga Guillot defects from Cuba while on tour in Venezuela. She is one of many artists who leave the country in the early '60s, while free travel is still permitted. The singer, who became known in the U.S. in the 1940s for her Spanish cover of "Stormy Weather," would later live quietly in Miami. She died there in 2010.

1962
-After shutting down all private radio stations, the Cuban government creates the Instituto Cubano de Radiodifusion, which will control all the stations on the island.

-Billo's Caracas Boys release "El Son Se Fue de Cuba," a nostalgic lament about the day the music died in Cuba (Jan. 1, 1959). Crooner Fernando Albuerne later records a version that becomes popular among Cuban exiles in the U.S.

This Ain't No Buena Vista: 5 Cuban Artists to Watch

1963
Pete Seeger releases his version of the Cuban song "Guantanamera" on the album We Shall Overcome, recorded live at Carnegie Hall in 1963. In 1999, Seeger would travel to Cuba to accept a humanitarian award.

1964
-EGREM, the national record label of Cuba, is founded. Recordings are made in the former Panart Records studio in Old Havana.

1967
-A Protest Song Festival is held in Havana, showcasing the strength of Cuba's government-sponsored Nueva Trova folk movement, whose members are influenced by Bob Dylan and Joan Baez as well as by their Latin American peers.

1979
-Afro-Cuban jazz group Irakere wins the Grammy for Best Latin Recording. The unlikely award was the result of an initiative of then-CBS Records head Bruce Lundvall, who took advantage of the first opening of a door in U.S.-Cuba relations under Jimmy Carter. Lundvall signed Irakere and took them to Carnegie Hall, where they recorded a self-titled live concert album.

-CBS Records’ Bruce Lundvall and Fania's Jerry Massucci organize Havana Jam, a three-day festival at the Havana's Karl Marx theater. Billy Joel, Weather Report, Kris Kristofferson and the Fania All Stars were among the performers who joined Cuban artists on stage. The concerts were attended by Cuban government officials and members of the elite.

1980
-The Mariel Boatlift brings a reported 125,000 Cubans to Florida. Many of the emigrants were convicts who came directly from Cuban jails, and who inspired the character of Tony Montana, played by Al Pacino in Brian de Palma’s Scarface (1983). The movie became a cult classic in the American hip-hop community.

1985
-Twenty-two-year-old Cuban pianist Gonzalo Rubalcaba performs with Dizzy Gillespie and his band at the1985 Jazz Plaza Festival in Havana. The trumpeter and the pianist played a duet on Gillespie's "Con Alma," moving Gillespie to proclaim that Rubalcaba was the best piano player he'd heard in 10 years.

-Miami Sound Machine's "Conga," reaches No. 10 on the Billboard Hot 100, bringing the flavor of Emilio and Gloria Estefan's Cuban roots to the pop mainstream.

1988
-Citing the First Amendment right to freedom of expression, the Berman Amendment to the Trading With the Enemy Act allows for the import of cultural goods to the U.S. from Cuba, including music. In addition to opening the door for albums made in Cuba to be sold in the United States, the legislation allows U.S. record labels to license and distribute music from the island. The ruling allows for new music from Cuba to enter the U.S. after an absence from the market of almost thirty years. The law also allows that music can be exported from the U.S. to Cuba.

Willy Chirino Op-Ed: Why U.S.-Cuba Thaw Is No Victory

1991
-David Byrne travels to Cuba and subsequently puts out a compilation of tracks by revolutionary folk singer Silvio Rodriguez, the first record in his label Luaka Bop's Cuba Classics series.

1992
-Following the collapse of the Soviet Union, Cuba loses the former bloc's economic support and enters a time of desperation known as the Special Period. As many Cuban citizens starve, the government looks to tourism as a solution to its deep financial crisis. Timba, a new kind of hard-hitting, sometimes dirty Afro-Cuban dance music that sounds like salsa on streroids, deals with social themes like prostitution. Some bands, like the popular Charanga Habanera, battle with government censors. As timba’s popularity with tourists grows, the artists achieve a kind of financial success previously unknown to musicians in Communist Cuba.

1993
-Actor Andy Garcia lifts Israel "Cachao" Lopez out of obscurity with the documentary about the Mambo pioneer, Como Mi Ritmo No Hay Dos, which premieres at the London Film Festival. The musician and composer was playing weddings and bar mitzvahs before being rediscovered through Garcia. He went on to win three Grammys for his subsequent recordings before his death in 2008 at age 89.

1994 
-Cuba signs the Berne Convention for the Protection of Literary and Artistic Works, thus agreeing to conform to the standards of international copyright law for the first time since the revolution.

-Hope turns to tragedy as desperate Cubans leave the island on homemade rafts; many perish. Among the balseros fleeing a Cuba in crisis, and others who arrive in the United States by plane or on foot over the border with Mexico, are artists and members of Cuban intelligentsia who leave the country en masse. Virtuoso Cuban musicians in the United States who have been schooled in Cuba’s state-run conservatories from a young age make a home in the United States, particularly Miami. Some find work as sidemen where for Ricky Martin and other Latin pop stars. Café Nostalgia, a new club in Miami's Little Havana with a house band of these musicians, caters to recent arrivals from Cuba. There, Cuban Americans drawn to the music come face to face with what they left behind.

1995
-The Habana Hip Hop Festival has its debut. Dead Prez and Common are among American rappers who appear at future editions of the festival.

1996
-Cuban national Gonzalo Rubalcaba receives death threats before a scheduled concert at Miami's Gusman Theater. Demonstrators outside the theater, flanked by police, spit on ticketholders, calling them prostitutes, Communists and traitors as they go inside. Many are deterred from entering. Despite warnings from his manager, Rubalcaba sits at the piano in the sparse house. He plays John Lennon's "Imagine." Rubalcaba would became the first music artist to freely travel back and forth to Cuba after becoming a U.S. resident.

1996
-The Helms Burton Act strengthens the embargo against Cuba.

1997
-Timba group NG LA Banda perform at New York’s Lincoln Center. The band leads an ecstatic audience in a conga line out the door of the theater.

-Nonesuch Records releases Buena Vista Social Club, produced by Ry Cooder at the Egrem/Panart studio in Havana. The recording of a gathering of a mostly forgotten group of Cuban seniors becomes a worldwide phenomenon. Cooder later is fined by the treasury department for working in Cuba.

1998
-Abdala, a new recording studio, opens its doors in Havana, instigated by singer Silvio Rodriguez. Former Fania Records engineer Jon Fausty flies from New York to Havana to advise the Cubans on recording technology for the new rooms.

-Executives from EMI are among the attendees at Havana's Cubadisco a music conference started in 1997 to bring Cuban music to foreign markets.

1999
-Gladys Knight, Woody Harrelson, Me'Shell NdegeOcello, Burt Bacharach and future Blue Note president Don Was are among the participants in Music Bridges, a weeklong songwriting exchange with Cuban artists in Havana that culminates in a concert at the Karl Marx Theater.

-Los Van Van, the most popular dance band in Cuba, sparks vehement protests when they perform at the Miami Arena, where police in riot gear are called to protect concertgoers, some of whom wear masks for fear of reprisals from 7,000 Cuban exile demonstrators. Promoter Debbie Ohanian, who stood her ground in spite of death threats and criticism from Miami's mayor, later won a lawsuit against the city of Miami for reimbursement of $36,000 in security fees she paid to secure the venue.

2003
-In the wake of 9/11, the State Department stops issuing performance visas to Cuban artists. No artists would be granted a visa again until 2009.

2005
-Audioslave performs for 70,000 at a free outdoor concert in Havana.

2006
-Pitbull posts anti-Castro song "Ya Se Acabo (It's Over)" on his Myspace page. A fan video for the track, which includes the line "I'm hoping he's dead because we don't need him," currently has over two and a half million plays on YouTube.

2013
-Jay-Z and Beyonce travel to Havana on a cultural tour. The celebrity couple are mobbed by Cubans in the street when they venture out of the upscale Hotel Saratoga. Their trip includes visits to the music conservatory and private music and dance performances.

-Los Van Van's Juan Formell is named Latin Grammy Person of the Year and honored at a dinner in Las Vegas. He dies less than a year later in Havana, at the age of 71.

2014
-Cuban singer Diana Fuentes, who lives in Puerto Rico, releases Planeta Planetario on Sony Latin. The album is also released on Egrem. It marks the first time an artist has a simultaneous release on an American and Cuban label.

-Associated Press publishes an investigative report detailing a USAID plot to infiltrate the Cuban hip-hop scene to create unrest among Cuban youth.

-The Cuban cast of Rent prepares for the production's premiere in Havana on Christmas Eve. It is the first Broadway musical to be staged in Cuba in five decades.

-President Obama announces a "new approach" to Cuban policy. As detailed by the White House, the new regulations will make it easier for American artists to travel to Cuba to perform. Cuba could even plausibly become a profitable touring destination for the first time in five decades if as yet unspecified amendments to regulations of Treasury Department regulations under the U.S. trade embargo are made, allowing U.S. artists and promoters to profit from concerts in Havana. 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.

-Enrique Iglesias' "Bailando," featuring co-writer Descemer Bueno and his fellow Cubans Gente De Zona, sets a No. 1 record on Hot Latin Songs, topping the list for 33 weeks. 

-Cubans get ready to celebrate the 56th anniversary of the revolution on New Year's Day.