Updated

With passport stamps from friendly visits to Venezuela, Cuba, Iran, and Saddam Hussein's Iraq, actor Sean Penn has been known to cozy up to the occasional dictator. But the two-time Academy Award winner and self-styled political activist had a strongly-worded message for the Iranian government on Monday.

Penn, along with other Hollywood moguls, is joining Amnesty International in condemning Iran for jailing native film director Jafar Panahi, the human rights organization announced earlier this week.

Panahi and his colleague Mohammad Rasoulof were sentenced to six years in prison this month for disseminating "propaganda against the state." The internationally-acclaimed director drew the ire of Iranian authorities for allegedly criticizing the government and inciting protests against it.

"The persecution that Panahi and Rasoulof are experiencing shouldn't exist in this day and age," Larry Cox, executive director of Amnesty International U.S.A said in a statement, calling the work of Penn and the effort's other Hollywood supporters "emblematic." "We are honored and grateful to have their support as we fight for Panahi and Rasaulof's freedom."

It's not the first time Penn has piped up about the workings of a dictatorial regime. While he's known for his defense of the helpless, such as Hurricane Katrina victims and Haitian orphans, he's also known for his defense of the not-so-helpless Venezuelan dictatorial leader Hugo Chavez.

"Every day, this elected leader is called a dictator here, and we just accept it, and accept it," Penn said in a March appearance on HBO's "Real Time with Bill Maher." "And this is mainstream media, who should - truly, there should be a bar by which one goes to prison for these kinds of lies."

During his last visit to Iran, it was the American media - not the Iranian government - that tripped into Penn's crosshairs. After filing a series of reports from Iran in 2005 for the San Francisco Chronicle, the actor lambasted journalists for "dismissive editorializing" and "trivial attacks" when a CNN report placed him in the country after he had already left.

"What we know of Iran comes largely from news sources," he wrote. "But if news sources can't track the current whereabouts of an actor-journalist, can we depend on the accuracy of the information we are receiving about Iran?"Penn continued, "And with Iran now in the crosshairs of a nuclear debate, we might note that the most costly and competitive arms race in the world is taking place right here at home, between Los Alamos and Livermore laboratories."

Penn was honored by the Film Museum of Iran during his 2005 visit.