Before You Go Guide to Cuba
Before You Go: MUSIC
*Francisco Cespedes: Album: "Con el permiso de Bola"
"Bola" is Bola de Nieve ("Snowball"), the late Afro-Cuban composer, singer, and pianist known for his raspy voice. On this album, Cespedes (an Afro-Cuban now living in Miami) reinterprets Bola's songs with an incredible balance of fidelity and originality. I can listen to this CD all day and not get tired, and every time, I hear something new.
*Bamboleo: Album: "No, Que Buena Esta":
Don't settle for just any Bamboleo album; this is THE essential Bamboleo record and "Yo No Me Parezco a Nadie" is THE essential Bamboleo song. If you don't move to this song, you better check your pulse. A great example of Cuban timba music.
*Pablo Milanes, Carlos Varela, and Silvio Rodriguez:
These are three different singers, but are the Bob Dylans of Cuba. All three are famous--and justly so--for their folksy anthems.
Before You Go: BOOKS
*The Handsomest Man in Cuba: by Lynette Chiang
Lynette's book is a travelogue that recounts her trip--by folding bicycle--around Cuba. Her stories are clear-paned windows into Cubans' daily lives, and the book's value is amped up by the nice resources section in the back. This book is especially great for someone who plans to cycle around Cuba.
*The Cuba Reader: edited by Aviva Chomsky & Pamela Maria Smorkaloff
I've sung the praises of the Reader series (which includes titles on Brazil, Argentina, Costa Rica, Mexico, Peru, and others) elsewhere, but it really can't be beat. In a manageably sized anthology, The Cuba Reader manages to deliver excerpts of seminal historical texts written in and about the island, giving you, at the very least, a comprehensive introduction to Cuba.
*Havana: Autobiography of a City: by Alfredo Jose Estrada
Whether you agree with the idea that a city can have an autobiography penned by a writer, Estrada's book is an excellent Havana primer. I found the introduction to be particularly apt and moving.
The recommendations here are all English-language books. If you'd like Spanish language recommendations, including books written by Cubans in Cuba, send me a message.
Must-See Movies
(As of this writing, all but one of these movies are available through Netflix)
*"Inventos: Hip Hop Cubano": If you're all interested in rap or hip-hop, you'll be interested in the still unfolding story of Cuban hip-hop told in "Inventos." If you're interested in traditional Cuban music, you're equally likely to find this documentary interesting. The word "inventos" refers to the inventive approaches the musicians have to take to play and perform: from fabricating parts to fix broken sound systems to cajoling local politicians to permit the now-famous hip hop festival to go on.
*"Balseros": This documentary focuses on Cubans who left the island bound for the US on homemade rafts during the 1994 exodus. The "Balseros" exodus was the most recent mass exodus by sea from Cuba.
*"Yank Tanks": This documentary is a must-see for classic car lovers, but if you don't consider yourself an auto aficionado (I don't), you'll probably enjoy "Yank Tanks." Learn all the tricks Cubans use to keep 1950s era cars running, and you'll get a peek into the daily life that requires all sorts of "inventos."
*"Cuba Mia": Another music-related documentary, "Cuba Mia" profiles the all-female orchestra, Camerata Romeu. What I love about this documentary is the way it shows how integral music is--whatever the genre--to daily life in Cuba. As a young woman practices her violin on the balcony of her apartment building, no neighbors shout for her to stop. Instead, they come out on their own balconies or into the courtyard and listen with reverence and joy.
*"A Night in Havana: Dizzy Gillespie in Cuba": See what happens when musicians dare to cross borders that politicians build.
*"El Tropical": Yet another music documentary (this one about the famous El Tropical night club), but also so much more, this is an astute social commentary about (among other topics) contemporary race dynamics in Cuba.
*"Cuban Story": Described by one reviewer as "One of the oddest pieces of film to come down in the pike in a while," this documentary made by Victor Pahlen and Errol Flynn and found by Pahlen's daughter, Kyra, after his death, is a historical treasure and, especially in the beginning, is great for some pot-shot laughs. A seemingly drunk and loopy Flynn narrates--complete with chalkboard sized map, wooden pointer, and props. What's interesting though, is that the film was made in 1958 and 1959, right in the midst of the Revolution's triumph, and Flynn, as he says, "went to see for myself" what was going on.
This is by no means an exhasutive list-- I've left out popular and perennial favorites (Fresa y Chocolate, for one) and classics ("Las Doce Sillas," "Guantanamera," "Lista de Espera," "Se Permuta," "Hasta Cierto Punto," to name only a few)--but the movies listed here are some of my favorites that give a window into real life, and are a great pre-trip orientation.

You're welcome! Glad you found it useful. And Cuban Story... isn't it just a find?!
Thanks for this. I really loved Cuban Story.