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Can cultural outreach soften the iron grip of an authoritarian regime in a way that sanctions or diplomacy could not?

Former professional basketball player Dennis Rodman appears to believe so, or at least for Kim Jong Un, a man who Rodman describes as a friend. But Kim also happens to be the head of one of the most oppressive regimes on Earth and just last month executed his own uncle.

Rodman might not be an expert in international relations or diplomacy or military history or human rights or the Korean peninsula; but no doubt bringing whatever talents and celebrity he has to North Korea has ignited international criticism of what he terms "basketball diplomacy."

Rodman isn't the first performer to bring his show abroad to brutal and repressive authoritarian regime.

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Entertainment acts making appearances for the benefit of foreign dictators isn't anything new.

"Godfather of Soul" James Brown, blues legend B.B. King, salsa star Celia Cruz and many others performed in 1974 in what was then known as Zaire at a festival sponsored by the regime of dictator Mobutu Sese Seko, as shown in the 1996 documentary "When We Were Kings" and the 2008 documentary "Soul Power."

Mobutu's dictatorship lasted for three decades, all that time looting billions of dollars and committing widespread human rights abuses.

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In 2007, Canadian artist Nelly Furtado performed for former Libyan dictator Moammar Gaddafi's family in Italy. Four years later, when Gaddafi used brutality to suppress protests that arose in the north African nation in the spirit of the Arab Spring, Furtado took to Twitter to announce that she would donate the $1 million she earned from the perfomance to charity, as reported by Reuters.

Furtado's announcement triggered other performers to make similar statements regarding their participation in events hosted by the Gaddafi family.

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Singer Beyonce Knowles also performed at a New Year's party for the family of the ex-Libyan strongman in 2009.

In 2011, Beyonce issued a statement acknowledging the links of a third-party promoter and noting that the $1 million she received to perform went to Haiti earthquake relief.

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Beyonce wasn't the only major celebrity at that New Year's Eve party for the Gaddafi clan in 2009. R&B singer Usher also was in attendance. And like Beyonce and others, when Libya became engaged in a violent civil conflict in 2011, Usher expressed regret over his involvement, promising to pass on his earnings to various charities.

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Singer Mariah Carey also acknowledged having performed for the Gaddafi family, attending a New Year's Eve party the year before Beyonce's appearance.

Although she claimed horror and embarrassment for her performance, Carey in 2013 was paid a rumored $1 million for a concert for Angolan President José Eduardo dos Santos.

Dos Santos has been in office for nearly 30 years, in a country that, despite its wealth of natural resources, is among the poorest of Earth, with about 68 percent of the population surviving on surviving on less than $1.68 per day.

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The Gaddafi family sure must be big fans of Western pop and rap music. In 2005, the Gaddafis hired rapper 50 Cent. Like other artists, 50 Cent announced his regret for the performance and promised to make a donation to Unicef.

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According to the Human Rights Foundation, singer Jennifer Lopez has raked in upwards of $10 million by "serenading crooks and dictators from Eastern Europe and Russia."

Last summer, Lopez earned a reported $1.5 million for performing at the birthday of President of Turkmenistan Gurbanguly Berdimuhamedow, whose unchallenged government has created one of the world's most repressive countries, according to Human Rights Watch, devoid of basic freedoms. Lopez's publicist claimed the singer would have not participated had there been "knowledge of human rights issues of any kind."

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In 2009, Sting performed at an event in Uzbekistan for Gulnara Karimova, the daughter of dictator Islam Karimov. The Uzbek leader's list of human rights abuses includes torture, kidnapping, rape, murder and more.

Rather than being contrite for his participation, Sting instead defended his involvement, stating: "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 counterproductive, 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."

Sting does show some discrimination as to which repressive regimes he will offer his services. In 2011, Sting canceled a concert in Kazakhstan after learning of a crackdown on an oil strike that left over a dozen people dead and many more imprisoned, beaten and tortured.

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Kazakhstan, which has been described by the Human Rights Foundation as a "human rights wasteland", couldn't land Sting, but a $3 million fee was enough to lure Kanye West to perform for the grandson of Kazakhstan's president Nursultan Nazarbayev.

Over the nearly 25 years Nazarbayev has held onto power, his regime has been criticized for widespread corruption, political manipulation and the use of force to silence dissent.