Guerra was born and grew up in Santo Domingo. After a year of study in philosphy 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 Rodriguez y Facundo Cabral.
After finishing his study at the Santa Domingo conservatory, Guerra went to the Berkee 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 el 440.
Three albums followed, Mudanza y Acarreo, Mientras mas lo Pienso and Tu. 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 1988, 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 440 band began touring. In 1991, they released their next album, Bachata Rosa, which also became a major hit.
Guerra became a controversial figure in the Dominican Republic after he released his next album, Areito. He protested against the poor conditions many Dominicans live in, and some of his countrymen felt that he wasn't the most appropriate person to protest, alleging that Guerra, in their opinion, had never faced poverty. That situation might have done something to do with his next album, Fogarate (1995), where he stayed away from singing any protests.
His most recent album, Ni es lo Mismo ni es Igual (1998) , proved to be a critically acclaimed work. It won three Grammys, which were given to him at the 2000 Latin Grammy awards.