That's what she did when she serenaded Gurbanguly Berdimuhamedow, president of Turkmenistan, over the weekend.
Turkmenistan is known as one of the "world's most repressive countries," according to Human Rights Watch. The former Soviet bloc country is regularly criticized for its poor treatment of women, the condition of its prisons as well as the intimidation of journalists.
But J-Lo didn't know any of that, and if she had, says her rep, she wouldn't have accepted $1.5 million for the pleasure of singing to its head of state.
Alas, it's not the first time Jenny from the block has committed such a faux pas.
In the past, she has performed for similarly generous sums of money for a controversial Uzbek businessman, according to the Guardian, as well as Azeri oligarch Telman Ismailov.
Not the greatest track record, to be sure. But it appears she is in good company.
Beyonce performed for late Libyan leader Muammar Gaddafi, Reuters reported. She sang for the family and its entourage at a private party on the Caribbean island of St. Barts in 2009. After being roundly criticized, she said she would donate the money from the party to a charity working in Haiti.
2) MARIAH CAREY
Mariah Carey also performed for the Gaddafi clan and said she felt "horrible and embarrassed" afterwards, according to Reuters. She also pledged to donate proceeds to charity.
3) NELLY FURTADO
Singer Nelly Furtado gave a private concert for the Gaddafi clan in 2007, according to the BBC. She also said she would donate the $1 million she made from her efforts to charity.
4) SHARON STONE
Actress Sharon Stone was notoriously present at Russian President Vladimir Putin's rendition of "Blueberry Hill." In this video below you can also spot Goldie Hawn, Kurt Russell and Gerard Depardieu.
5) NAOMI CAMPBELL
Let's not forget Naomi Campbell, who after a 1997 dinner at Nelson Mandela's home in South Africa, allegedly accepted the gift of a "blood diamond" from former Liberian President Charles Taylor. The supermodel later testified at Taylor's war crimes tribunal in 2010. Campbell told the International Criminal Court that she had received a gift of “dirty-looking” raw diamonds from unknown men, assumed to have been sent by Taylor.
6) DENNIS RODMAN
Perhaps the most recent celebrity other than Jennifer Lopez to make a splash cozying up to a strongman was Dennis Rodman, who became the first American to meet North Korean leader Kim Jong Un when he made a surprise visit there in February.
7) HILARY SWANK
Actress Hilary Swank attended the birthday party of Ramzan Kadyrov, the Chechen leader accused of torture, abductions and killings. At a party in October 2011, Swank reportedly said she had been taken by the Chechen government's "passion to make peace and to make something beautiful," though she later apologized for doing so.
Here's someone who's not sorry, however: Sting. In 2009, the British popstar performed for the daughter of the Uzbek president, Islam Karimov. Unlike J-Lo, he had done his homework. He said at the time he was well aware of Karimov's reputation, and that he felt his performance had been justified.
“I am well aware of the Uzbek president’s appalling reputation in the field of human rights as well as the environment," he said, according to the Telegraph.
"I made the decision to play there in spite of that," Sting continued. "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.”