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

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.

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