Many of his songs have become classics in Latin American music, such as "Ojalá", "Playa Girón", "Unicornio", "Sueño con Serpientes", "Vamos a andar," and "La maza".

Rodríguez was born on 29 November 1946 in San Antonio de los Baños, a fertile valley in Havana Province known for its tobacco crop.

A few years later, he participated in the music competition Buscando una estrella ("Looking for a Star"), hosted by the now-defunct Cuban radio station CMQ.

He was invited a few days later to participate in a musical competition for children held by the same station, this time directed by the well-known announcer Germán Pinelli.

At nine years old and motivated by his father, who read him poems by José Martí and Rubén Darío,[6] among others, he took an interest in literature, paying attention to the work of both poets, as well as the genre of science fiction.

[7] On January 1, 1959, when Rodríguez was thirteen years old, Fidel Castro's Éjercito Rebelde brought an end to the dictatorship of Fulgencio Batista.

Despite regularly traveling between his hometown and the capital, he enlisted in the San Antonio de los Baños chapter of the Association of Socialist Youth, created by Che Guevara.

[7] The following year, amid social tension due to Cuba's nationalization of businesses and the United States' embargo, his parents separated once again, this time indefinitely.

[7] In January 1961, the United States broke diplomatic relations with Cuba following the election of president John F. Kennedy, who authorized the Central Intelligence Agency (CIA) to invade the country.

There, he helped give the campesinos classes in history, geography, grammar, and mathematics, as well as explaining elements of the new government, such as the Agrarian Reform plan.

Rodríguez began to read the works of Federico García Lorca, Pablo Neruda, Guillén, Edgar Allan Poe, and Walt Whitman.

One of his colleagues, Lázaro Fundora, played the guitar as a hobby and taught Rodríguez the first chords of the instrument that would become a key part of his future work.

[8] In 1963, with the birth of his second sister, Anabell López, the daughter of his mother and Rolando, Rodríguez began his studies in painting at the School of San Alejandro, in Havana.

He joined the Fuerzas Armadas Revolucionarias (FAR), where he would meet Esteban Baños, a member of his unit who gave him further instruction in playing the guitar.

In 1965, he transferred to the magazine Verde Olive, where he remained until the end of his military service, working during the day and teaching himself the guitar at night.

[11] In 1967, just before completing his military service, Rodríguez won an honorary mention in the literary competition of the FAR for his book of poems Honradado Cuaderno No.

On that occasion, Rodríguez performed "Es sed", "Sueño del colgado y la tierra", and "Quédate", the latter of which appeared later on his album Expedición, released in 2002.

His lyrics are a staple of leftist culture throughout the whole Spanish-speaking world, and he has been banned from the media during several of the dictatorial regimes that ruled Latin America in the late 1970s and early 1980s.

In the middle of his career, Silvio Rodríguez experimented with sounds and rhythms departing from his trademark acoustic guitar, accompanied by the group Afrocuba (e.g. in Causas y azares).

At maturity, Silvio Rodríguez thoroughly purified his sound through a return to acoustic guitar, great care and sophistication in the voice, and exclusive control of the production process from beginning to end.

His lyrics became more introspective, at times even self-absorbed or self-justifying, expressing melancholic longings about the shortcomings of real-life socialism in Cuba while vindicating idealism and revolutionary hope amongst the youth.

In a similar way, the unusual confessional tone of many of his songs allows for an unorthodox combination of transgression, eroticism, longing, and at times (probably accurate) self-deprecation in many of his lyrics.

If the lyrics of the early part of his career are about revolutionary enthusiasm, love encounters and disappointments, as well as sensual desire, and if the middle-aged Silvio is more self-questioning, often looking backward; his most recent albums, such as Cita con ángeles, talk in part about his life as a grandfather and has a certain focus on children, while Érase que se era is the release (with all the means that come with being an established artist) of songs written early in his youth but never previously recorded.

[17] Silvio Rodríguez has been denied a United States visa several times, and it was particularly controversial in 2009 when he was invited to celebrate the 90th birthday of Pete Seeger.