It is generally acknowledged that the bolero is a musical genre born in Cuba in the 19th century and a descendant from the Cuban "canción", or song. Several other styles or genres are similarly related, such as trovador songs and habaneras.

Although the bolero was also known in Spain, there are significant differences between it and the version known throughout Latin America. One major difference is in the form of dancing associated with the music of the Spanish bolero. The Spanish version was danced by groups of couples that danced apart, in contrast to the Latin American style of couple-centric pair dancing together. Another major difference is that the Spanish version is written in 3/4 time while the Latin American version is in 2/4 time. Of course, yet another and most important differentiator is the influence of African-based rhythms at the foundation of the Latin-American bolero.

One of the first well known Latin-American bolero composers was José Pepe Sánchez, from Cuba. It is known that he composed a song in 1885 called "Tristezas". The song had two phrases, each of 16 measures. Between these phrases was an instrumental section where the melody was carried by a guitar. A typical Cuban bolero is the following example, entitled Condición. Famous Cuban musician Paquito D'Rivera once suggested that the modern Latin-American bolero was "a ballad with a little black beans on the side", perhaps in jest, but suggesting the influence of the more energetic rhythms on the lyricism of the Latin-American bolero.

The bolero quickly spread to Puerto Rico and throughout large parts of Latin America. Particularly noted among the Puerto Rican composers in the bolero genre are Rafael Hernández and Pedro Flores. Several famous trios sprang up to perform their works; eagerly consumed by a public that yearned for the soulful songs on the universal theme of love in all its variations: eternal love, unrequited love, love lost, and separation. Some of the more reknown of these modern troubadours were Trio Los Panchos and Trio Vegabajeño (see Bolero artists page for more). Of course, bolero artists were not limited to the trios, as soloists such as Julita Ross and others would show.

Naturally, some of the best known exponents of the modern bolero in Latin-America are from Cuba. The political situation in Cuba has unfortunately hidden many of these talented composers and performers from large parts of the rest of the world. Fortunately, the recent Ry Cooder project that resulted in the hugely successful and Grammy-winning Buena Vista Social Club video and the related recordings, have put the spotlight back on Cuba and figures such as Ibrahim Ferrer. Cooder himself said of Ferrer" "..the last of the great bolero singers. Everybody in Cuba can play good, but voices of this quality are much rarer".

But artists like Ferrer and the old trios, are not the only source of boleros. Modern exponents include artists like Los Tri-O, a group of young bolero singers who have sold millions of records in the United States and Latin America. Their critics admire the effort but bemoan the lack of faithfulness to the genre. Some say that Lucrecia, a sultry Cuban chanteuse who lives and records in Spain, has been one of the few Latin performers of the '90s able to resurrect the bolero instead of desecrating it.

In any case, many of the older works are available on the latest CD media, to satisfy the demands of purists while others can take heart in the new generation of artists that will not let the genre die. Keeping the bolero genre alive is not limited to artists in Cuba and Puerto Rico. The sentiment is nearly universal across Latin-America, with bolero artists such as Juan Luis Giménez, from Brazil, as well as other artists from Mexico and elsewhere.