Six Movies to Watch Before You Travel to Cuba

President Obama announced last month that “the United States of America is changing its relationship with the people of Cuba.” What that meant for Americans who want to travel to Cuba was not clear. Now the new regulations have been clarified, and it’s sort of good news for those who want to go. It won’t be as simple as booking a flight to, say, Belize, but it’s less restrictive then before. Until you can make the trip, you can visit vicariously through the movies. Here are six stories all set on the Caribbean’s largest island. These are meant to be entertaining; they’re not harrowing documentaries, but each one gives us a look at life on our nearshore neighbor in one way or another, real or imagined.

Our Man in Havana (1959)

Actually filmed in Cuba shortly after the revolution, this brilliant dark comedy takes place shortly before the revolution. Alec Guinness, long before he became a Jedi master, plays a British vacuum cleaner salesman in Havana who agrees to set up a spy network for MI6. He gets caught up in his own trickery, and the results are not always comical. There’s a nefarious police captain, mysterious deaths, secret codes, Havana nightlife, lots of great shots of old Havana, and even foreshadowing of the Cuban Missile Crisis. The screenplay was written by sometime spy Graham Greene, based on his novel of the same name. According to some reports, Fidel liked the movie but thought it was too soft on the Bautista regime. Communists and capitalists alike will appreciate the depiction of the foibles of government bureaucrats. (Watch a scene at the Tropicana nightclub here, featuring the legendary Ernie Kovacs as the police captain.)

Buena Vista Social Club (1999)

This documentary helped remind the world of the wonders of Cuban music. In 1996 in Havana, American guitarist/music archivist Ry Cooder and Cuban bandleader Juan de Marcos Gonzalez gathered and recorded some of the island’s finest musicians. Most of them had fallen on less than easy times since the revolution. The album is named after a Havana social club where the older players used to perform. The movie shows the musicians in concert and traveling beyond their native island. The music is phenomenal, and the interviews with the old-timers are great. The movie, directed by Wim Wenders, does have its annoying tendencies, described well by Roger Ebert, but it also gives us a rare glimpse of life in Cuba. Ry Cooder was subsequently charged and fined by the U.S. government under the Doing Business with the Enemy Act. That’s what you get for spreading capitalism, citizen Cooder. (Trailer on YouTube.)

Brothers in Exile (2014)

It’s not just Cuban cigars that are illegal in the United States. So are Cuban baseball players. (Shortly after Obama’s announcement, Major League Baseball sent a memo to teams clarifying that they still couldn’t scout players in Cuba.) This ESPN production is the latest in a long line of documentaries about Cuban baseball. It features the fascinating stories of two Cuban brothers, Livan and Orlando Hernandez (whom NY Yankees and Mets fans will fondly remember as “El Duque”). Both were right-handed pitchers who fled Cuba to play major league baseball in the US. If you’re interested in Cuba or baseball, this is well worth your 90 minutes. (It’s available on YouTube.)

Pier 5, Havana (1959)

In this nifty B-movie, an American (Cameron Mitchell) goes to Cuba right after the revolution to investigate the disappearance of a friend. When he arrives in Havana, he is greeted by the police chief, and that’s where his troubles begin. Pursuing clues, unsure whom to trust, he uncovers a devious counterrevolutionary plot. Those with anti-Castro sentiments might not applaud the ending. Parts of the movie were shot in Cuba but sometimes what you are seeing is Santa Monica, California. (Currently available for streaming on Netflix.)

Una Noche (2012)

This is not exactly a lighthearted romp. In fact, it’s pretty bleak at times. But it’s a very good dramatic movie that provides us outsiders with a look at daily life on the edge in Havana. We spend a day with three Cuban teenagers, who plot their escape from the island. After seeing what their lives are like, that might not seem like a bad idea. First-time director Lucy Mulloy gets terrific, natural performances from the non-professional actors, and the extensive footage of actual Havana gives this film a feeling of realism. Speaking of reality: two of the film’s actors ended up seeking political asylum in the United States. (Watch the trailer here.)

The Godfather: Part II (1974)

You’ve probably seen this masterpiece, but watch it this time around for the scenes set in pre-revolution Havana (they were actually filmed in Santo Domingo, Dominican Republic). The film is pretty accurate in its depiction of American mobsters and their fondness for Havana, with its casinos, nightlife, easy living, and freedom from the U.S. Department of Justice. In this part of the Corleone saga, things could be unraveling, or they could all be coming together, and much of it hinges on things that happen on this island just 90 miles south of Miami.