A masterpiece of documentary film making by French writer/director/cinematographer Karim Dridi.
From the Internet Movie Database:
Seventy-six-year-old Cuban street musician Miguel Del Morales, known as El Gallo (The Rooster), travels around Cuba with his guitar, making music in the homes of friends, in bars, and on street corners, in courtyards and stairwells. His rich voice, colored by a lifetime of cigarettes and rum, weathered by the sun and rain, bespeaks the joys and sufferings of his countrymen. An urban troubadour, Del Morales has been called "a living memory of Cuban bolero."
Jazz on the Tube has an entire section devoted Cuba and its music.