The links I've included are a version available for download but if you don't like the particular version I've included, do your own search and find your own style.
"Tristezas" (Sorrows) is commonly considered the first bolero. Written in 1885 by Jose Pepe Sanchez, "Tristezas" is still performed to this day. Sanchez never had any formal musical training and the only reason that some of his boleros are remembered is due to friends and relatives writing down the songs they heard.
A staple in every bolero singer's repetoire, "Dos Gardenias" was composed by Cuban Isolina Carrilo in the 1930s and regained fame when it appeared on the original Buena Vista Social Club album where it was sung by Ibrahim Ferrer. Ferrer himself learned the song from the great Beny More when he played with him in the 1950s.
I really liked the version performed by Antonio Machin, one of the most recorded Cuban artists in history (right behind Celia Cruz).
Another standard in the repetoire of any bolero singer is "Veinte Anos." The bolero was composed by Maria Teresa Vera from Guanajay, Cuba. Vera was an outstanding guitarist, singer and songwriter; she spent 27 years performing with Lorenzo Hierrezuelo in the duo Los Compadres.
The Buena Vista Social Club gave the song a broad audience when performed by Omara Portuondo.
Hands-down, this is my personal favorite classic bolero. Composed by Panamanian Carlos Almaran and written to commemorate the death of the wife of Almaran's brother, the song has been performed by numerous artists and even served as part of a soundtrack of a 1956 movie by the same name.
Here's a version performed by the popular Mexican group Trio Los Panchos. Eydie Gorme often sang the song with the trio, by I like this version by with just the trio.
One of the most popular boleros of all time, "Solamente Una Vez" was composed by Augustin Lara in 1941. The prolific Mexican composer from Veracruz wrote more than 800 compositions including "Maria Bonita", "Noche de Ronda" and the perenniel classic "Granada." The bolero was subsequently recorded in English as "You Belong To My Heart" and made famous by Bing Crosby and Xavier Cougat.
Here's a lovely version sung by Placido Domingo, the late Luciano Pavarotti and Jose Carreras - also known as 'The Three Tenors.'
With so many artists covering this bolero, I picked one that was more traditional although the songs has been adapted to many styles and singers, both sad and slow and also with a little kick.
"Involvidable" means 'Unforgettable' but unlike the Nat King Cole song that was written by Irving Gorden in 1951, this famous Cuban bolero was composed by Julio Gutierrez in 1944.
Subsequently recorded by many artists, "Inolvidable" was a big hit when sung by Tito Rodriguez on From Tito Rodriguez With Love in 1963, selling over 1.5 million copies. Rodriguez was one of the original Mambo Kings and for years vied with Tito Puente for first place in the hearts of mambo fans everywhere.
Here's a modernized version of the classic sung by the popular purveyer of romantic music, Luis Miguel.
"Guantanamera" is probably the one Cuban bolero that even those people not addicted to Latin music have heard. Recorded by Tito Puente, Celia Cruz and a host of others, Trini Lopez brought the song to a whole new generation.
Composed by Joseito Fernandez (Jose Fernandez Diaz) in 1929, 'Guantanamera' means a peasant woman from Cuba's Guantanamo province; the original lyrics were also written by Joseito Fernandez about a woman he loved and who left him. But these are not the lyrics that we're familiar with; over time the original lyrics were replaced with the first stanza of a poem written by Cuban hero Jose Marti from his "Versos Sencillos."
10. "Somos Novios"
If you know the song "It's Impossible" then you know the "Somos Novios." Composed by Mexican bolero icon Armando Manzanero, the song became popular globally when Perry Como recorded "It's Impossible" in 1971. This version of the song about newlyweds is a recent duet by pop singer Christina Aguilera and Italian tenor Andrea Bocelli.