The actor has long been known for his liberal views. He first visited Caracas in the role of a freelance journalist in 2007, when Chavez had just watched "Mystic River" and the two shared a hatred of the Bush administration and the Iraq war. After the visit, Penn called Chavez “much more positive for Venezuela than he is negative” and referred to the Chavez-crafted constitution as “a very beautiful document.” Penn also said on the David Letterman show afterward, "He's done incredible things for the 80% of the people who are very poor there." The next year, Penn visited Chavez again, going on a tour of a natural gas pipeline with the Venezuelan leader.

And again in 2009, Penn paid a visit to Chavez, where the two talked about a possible film project and discussed President Barack Obama's term thus far. Penn raised eyebrows even further in March 2010, when he said on HBO's "Real Time with Bill Maher" that media critics who refer to Chavez as a dictator should be jailed: "There should be a bar for which one goes to prison for these kinds of biases," Penn said. Chavez publicly thanked Penn afterward for defending him from his critics.