Anne Applebaum has a good theory:
"In fact, for the malcontents of Hollywood, academia, and the catwalks, Chávez is an ideal ally. Just as the sympathetic foreigners whom Lenin called "useful idiots" once supported Russia abroad, their modern equivalents provide the Venezuelan president with legitimacy, attention, and good photographs. He, in turn, helps them overcome the frustration John Reed once felt—the frustration of living in an annoyingly unrevolutionary country where people have to change things by law. For all his brilliance, Reed could not bring socialism to America. For all his wealth, fame, media access, and Hollywood power, Sean Penn cannot oust George W. Bush. But by showing up in the company of Chávez, he can at least get a lot more attention for his opinions."
For a regrettably large number of Hollywood big shots, the reality of life in a repressive dictatorship is lost on them. They are easily deceived. This is why a guy like Hugo Chavez can cast himself as a man of the people and a friend of democracy, (much like Che continues to cloak his true bloody legacy even long after his death), while Penn, Redford, Danny Glover and others manage to miss the persistent details of reality.
She continues on:
Most of all, Venezuela's leader not only dislikes the American president—so do most other heads of state—but refers to him as "the devil," a "dictator," a "madman," and a "killer." Who cares what Chávez actually does when Sean Penn isn't looking? Ninety years after the tragedy of the Russian revolution, Venezuela has become the "kingdom more bright than any heaven had to offer" for a whole new generation of fellow-travelers. As long as the oil lasts."
Certainly seems that way.