After a year of study in philosophy and literature at the Universidad Autónoma de Santo Domingo, he switched to the Conservatorio Nacional de Música where he finished his undergraduate study. Guerra was a great admirer at this time of the nueva canción, embodied by Pablo Milanés, Silvio Rodríguez and Facundo Cabral. After finishing his study at the Santo Domingo conservatory, Guerra went to the Berklee College of Music in Boston to study composition and arranging. After his return to the Dominican Republic, he released his first album, Soplando (1984) with a group of local musicians which subsequently became known as Juan Luis Guerra y 440. The 440 part of the band's name refers to the standard tuning "A=440." Two albums followed, Mudanza y Acarreo and Mientras más lo pienso ... tú. Although they saw little acclaim internationally, the band garnered some fame in their country, resulting in them being nominated to represent the Dominican Republic at the prestigious Festival OTI. Their next album, in 1989, brought them international fame. Ojalá que Llueva Cafe became a number one hit in many Latin American countries, with the hit song of the same name. Subsequently, a video of the hit song was filmed and Juan Luis Guerra and his 4-40 band began touring. (The song's fame was revived in 1996 with a cover by Café Tacuba). In 1990, they released their next album, Bachata Rosa, which also became a major hit, selling more than 5 million copies at that time, and allowing Guerra to keep touring Latin America, USA and Europe. This album contains memorable love songs such as "Burbujas de amor" and "Estrellitas y Duendes". Guerra became a controversial figure in the Dominican Republic after he released his next album, Areito. "Areito" (1992), featured the hit single "El costo de la vida," ("The Cost of Living") but the video version was banned in several countries. He protested against the poor conditions in many Latin American countries, the celebration of the "Americas' Discovery, (1492)" and the double standard policies of first world nations. ('Areito' is a Taino word for song and dance). That situation might have had something to do with his next album, Fogaraté (1995), where he stayed away from recording any protest songs. One of his most recent albums, Ni es lo Mismo ni es Igual (1998), garnered much critical acclaim. It won three Latin Grammys in 2000. In 2004, Guerra released his first new album in six years. Entitled "Para Ti", the album's songs are mostly religious in nature, reflecting Guerra's conversion to evangelical Christianity. With this album the singer won two awards at the 2005 Billboards in the categories of Gospel-Pop and Tropical-Merengue. In the same time, Guerra was honored with the Latino Special Award for the Music Academy of Spain for his contributions to the music of his country and the Caribbean in the last 20 years.
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