Dennis Rodman's not alone: 4 other famous visitors to authoritarian regimes

Sean Penn, Sting, and Jennifer Lopez have also drawn criticism and raised questions over the value of entertaining rogue leaders.

While Dennis Rodman is perhaps the most outlandish celebrity to visit an authoritarian regime, he certainly isn't the first.

The former NBA star hosted an exhibition game between North Koreans and former NBA players today. He insists his trip is apolitical, although he has repeatedly professed his fondness for Kim Jong-un, his new “friend for life.” 

Mr. Rodman’s trips to North Korea have mainly drawn fire for their self-serving promotional nature and lack of comment on North Korea's egregious human rights record. A few observers have been cautiously optimistic that the visit could open the door toward better understanding between the secretive regime and the West.

One takeaway of the media hullaballoo is that celebrity status and little-understood regimes are an explosive mix. Because places like North Korea exist in a diplomatic vacuum – due to their isolationist policies, or international ostracizing, or both – a famous visitor can send a message of international legitimacy and, potentially, even tacit approval, despite their intentions.

In this, Rodman is in good company. Here are some other big names who have courted controversy through recent forays into authoritarian lands:

Sting in Uzbekistan 

British superstar Sting was unapologetic in 2009 for performing for the flamboyant daughter of Uzbekistan’s ruler Islam Karimov. Sting was generously rewarded for taking part in the concert and criticized when the amount – reportedly over $1.5 million – became public.

He later defended his decision to travel to Tashkent, saying that he had full knowledge of Uzbekistan’s human rights record but chose to take the trip anyway in order to build cultural ties and perhaps change a few minds in the process, according to the Guardian:

"I am well aware of the Uzbek president’s appalling reputation in the field of human rights as well as the environment.

I made the decision to play there in spite of that. I have come to believe that cultural boycotts are not only pointless gestures, they are counter-productive, where proscribed states are further robbed of the open commerce of ideas and art and as a result become even more closed, paranoid and insular.”

Sound similar to “basketball diplomacy?” Just as in Rodman’s case, many skeptics weren’t buying it. In the words of the former UK ambassador to Uzbekistan, Craig Murray: 

“He did not take a guitar and jam around the parks of Tashkent. He got paid over a million pounds to play an event specifically designed to glorify a barbarous regime. Is the man completely mad? 

I agree with him that cultural isolation does not help. I am often asked about the morality of going to Uzbekistan, and I always answer – go, mix with ordinary people, tell them about other ways of life, avoid state owned establishments and official tours. What Sting did was the opposite.”

Sean Penn in Venezuela

Actor Sean Penn developed a friendship with Venezuela's former leader, Hugo Chavez, starting in 2007, at a moment when relations with the US were particularly tense. Mr. Chavez even named Mr. Penn as someone he'd like to see picked as the US ambassador to Venezuela.

The friendship helped Penn earn goodwill in neighboring Bolivia, which may have helped him play a role in sneaking out an imprisoned US businessmen, Jacob Ostreicher, from La Paz last month. (Exactly how Mr. Ostreicher managed to leave Bolivia remains unclear.) 

Beyonce, Mariah Carey, and Usher in Libya

Before its downfall in 2011, the Qaddafi clan enjoyed the company of numerous international stars, including Beyonce, Mariah Carey, and Usher, all of whom received lucrative payments. All issued public apologies and donated their earnings to charity when reports of their performances emerged via Wikileaks.

Of the three, Mariah Carey offered up the most gushing public apology. Unlike Sting (who claimed to have done his research homework) and Dennis Rodman (who steers clear of these questions altogether), she blamed her visit on the lack of prior knowledge about Qaddafi’s abuses of power:  

"I feel horrible and embarrassed to have participated in this mess. Going forward, this is a lesson for all artists to learn from. We need to be more aware and take more responsibility regardless of who books our shows.

Ultimately we as artists are to be held accountable." 

Jennifer Lopez in Turkmenistan

A similarly contrite Jennifer Lopez apologized for taking part in a birthday concert for Turkmenistan leader Gurbanguly Berdymukhamedov in June 2013. “Had there been knowledge of human rights issues any kind, Jennifer would not have attended,” her publicist told The Associated Press. (It’s unknown whether she kept the fee.)