Sean Penn and Fidel Castro? The actor’s top 5 forays into journalism.

The star of "Milk", actor Senn Penn, is in Cuba, reportedly to interview Fidel Castro for Vanity Fair magazine about how the Obama administration has affected the island.

By Matthew Clark | Staff writer 10.26.09

Oscar-winning actor, political activist, and part-time Big Name interviewer Sean Penn is currently in Cuba hoping to land what may turn out to be the biggest “get” of all his journalistic dabblings.

He’s angling to interview ailing revolutionary leader Fidel Castro. And, if recent history is any guide, he’s got as good a shot as any imperialist Yankee to sit down for an on-the-record with the bearded ex-president. Last year, he sat down for a seven-hour gabfest with Fidel’s younger brother and current Cuban President Raúl Castro. (See below). And he hung out with Fidel back in 2005.

Celebrity news source TMZ.com reports that Penn is there to do a piece for Vanity Fair magazine on how the Obama administration has affected Cuba.

Cuba’s government-controlled TV showed Mr. Penn walking in the town of Nueva Gerona on the Isle of Youth, accompanied by Cuban painter Alexis Leyva. (Somehow, I doubt Penn will get stuck on the island begging ferry operators to bend arcane Communist rules to let us leave the way a Monitor photographer and I had to do while reporting a three-part series on how change is coming to Cuba.)

Penn’s latest foray into journalism prompts us take stock of the past few years of his reportage.

Herewith, the Top 5 Sean Penn reporting trips.

5) Iran. In 2005, Penn traveled to Iran to cover that country’s elections for the San Francisco Chronicle. The result: A five-day series. Here’s a sample:

Back at the hotel, I went for coffee and scrambled eggs at the downstairs buffet. A canned, Muzak version of “I Will Always Love You” plays. The scene downstairs reminded me of similar scenes in Iraq, at Baghdad’s Al Rashid and Palestine hotels. International journalists with that “What the [bleep] are you doing here, Mr. Penn?” look on their faces.

4) Iraq. In 2004, Penn reported for the San Francisco Chronicle that the occupation by US forces there “could ignite a powder keg.” This came a little more than one year after he used an ad in the Washington Post to ask former President George W. Bush not to go to war in Iraq. “I beg you, help save America before yours is a legacy of shame and horror,” Penn wrote in an open letter to Bush.

3) Cuba. Weeks before President Obama was elected last year, Penn had dinner and drinks with Cuban President Raúl Castro during a seven-hour conversation in Havana. Mr. Castro told Penn he’d be open to meeting with Mr. Obama, if he won the election. Penn wrote the visit up for The Nation, a liberal news magazine.

Penn flew to Havana from Caracas, Venezuela, on a plane loaned to him via the Venezuelan Ministry of Energy and Petroleum. Just don’t razz him about it. “If someone wants to refer to that as a payoff, be my guest,” he wrote. “But when you read the next report from a journalist flying on Air Force One, or hopping on board a US military transport plane, be so kind as to dismiss that article as well.”

Touché, Mr. Penn. Touché.

2) Venezuela. Before flying on to Cuba (see #3) Penn spent some time hangin’ with President Hugo Chávez, prompting this response by George Packer of The New Yorker:

Why does someone like Penn think he can do this job, which isn’t his job? Perhaps because he can write down and relay the words of famous people to whom his own fame gives him access, and because certain thoughts pass through his mind while he’s writing them down. Penn’s moonlighting shows a kind of contempt for journalism, which turns out to be rather difficult to do well. It also shows that he’s missed one of the main points of Obama’s election, which has Penn shedding tears at the end of his dispatch. Obama is the splendid fruit of a meritocracy. In a meritocracy, actors who act well get good roles. They don’t get to be journalists, too—a job that, in a meritocracy, should go to those who do journalism well. Nor should any journalist, however accomplished, expect to land a leading part in Penn’s next movie.

1) Fidel Castro doesn’t do many interviews these days. If Castro grants Penn an interview, it could be one of the last the leftist icon grants to a Western “journalist” – or movie star. And that would make it No. 1.

If you could get an interview with Fidel Castro, what would you ask him?

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