Remember when Sean Penn decided to back away from Hollywood to tend to his family? Well, that didn't seem to go too well. Only a short time later in August, Robin Wright Penn filed for divorce. So much for finding familial focus. With all that freed time, one might think he'd chill with his kids, or head back to acting. Nope. Why do that when you can hunt down dictators?

TMZ reports that Penn has once again put on his part-time journalist hat and flown to Cuba to hunt down an interview with Fidel Castro for Vanity Fair. He hopped on a plane with Diana Jenkins earlier this week in Las Vegas, headed for Havana. (I'm guessing that there's a stop along the way. As far as I know, flying from the U.S. to Cuba is not exactly okay.) But there's a little he-said, she-said among the sources. Barclays contacts say he's going there to meet Castro and talk about how the Obama administration has affected Cuba. Penn's rep told the site that a meeting is possible, but there's no current appointment or plan to meet with the dictator. Methinks that's just evading the topic. One doesn't go to Cuba, have no plans to meet with Castro, yet say that a meeting is possible.

Penn has entered sticky situations before -- most notably with Hugo Chavez, who he thinks is "much more positive for Venezuela than he is negative." But is that enough to make him the first Western journalist to interview the man in three years, since Castro stepped out of the spotlight?