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Despite being surrounded by handlers galore, even 1 percenters can make questionable travel choices.

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Dennis Rodman in North Korea

Not everyone can say they have Kim Jong-un on their short list of ride or dies, but former Chicago Bull Dennis Rodman did just that after traveling to Pyongyang to meet with the Supreme Leader in 2013. By all reports, the unlikely duo had a blast at a basketball game then at dinner with various North Korean officials, after which Rodman declared Kim his “friend for life.” He returned to North Korea the following year, this time with a group of retired NBA players. After singing a rousing rendition of “Happy,” the Worm led his team in an exhibition game played as a “present” to his “best friend.” The faithful-to-the-end Rodman even traveled to Singapore last June for a North Korea summit.

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Beyoncé and Mariah Carey in St. Barts

Imagine celebrating New Year’s Eve at a private bash at tony Nikki Beach Saint Barth. A favorite of A-list jet setters, the hot spot doesn’t disappoint, especially with headliners like Beyoncé and Mariah Carey. But there’s a slight catch: These fetes were hosted by the family of none other than Muammar el-Qaddafi. The Mad Dog of the Middle East helmed a government connected to terrorist attacks, including the 1988 Lockerbie bombing. Despite the host’s lineage, the parties drew well-known — if not well-informed — guests like Jay-Z, Russell Simmons and Jon Bon Jovi. And as it turns out, performing for the Qaddafi clan is quite profitable: Carey received $1 million to sing in 2009, and Beyoncé secured a cool $2 million the next year.

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Anthony Bourdain in Lebanon

The stewed lamb might have been to die for, but the bombs exploding during Anthony Bourdain’s 2006 trip to Beirut were far deadlier. While in the city filming for his Travel Channel series No Reservations, the late chef found his Lebanese foray quickly going south. Instead of focusing on the flavors and culture of the Middle East’s party capital, Bourdain and his crew found themselves on the front lines of a conflict. They spent 10 tense days in Beirut before being evacuated from the war-torn city thanks to U.S. intervention, a military landing craft and the USS Nashville. On the upside, the resulting episode was ultimately nominated for an Emmy.

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Naomi Campbell in South Africa

As the story goes, during a 1997 trip to South Africa for an event hosted by Nelson Mandela to support his Children’s Fund, Naomi Campbell was gifted “a few stones” by then-Liberian dictator Charles Taylor. Initially denying the accusation, the supermodel was issued a subpoena and warned she could face jail time if she refused to cooperate with the United Nations. She eventually testified that two men representing Taylor had come to her room late one night to give her “a pouch with a couple of dirty-looking stones.” Ultimately, Taylor was brought to trial in 2012 for his war crimes and found guilty of trading blood diamonds to fund a rebellion during Sierra Leone’s 10-year civil war. Campbell managed to escape charges, though one can assume (blood) diamonds are not that girl’s best friend. 

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Hilary Swank et al. in Chechnya

In addition to ruling what is quite possibly the most repressive country on the planet, Chechen leader Ramzan Kadyrov is perhaps best known as the first head of state to be banned from Instagram. But even if he can no longer document it on the ’gram, Kadyrov still loves a good party. And thanks to the absurd attendance fees he pays out — reputed to be in the area of half a million dollars — he doesn’t seem to have any trouble filling seats at his soirees. Hilary Swank, Jean-Claude Van Damme, Seal and violinist extraordinaire Vanessa-Mae are among the celebs who chose to put a Chechen stamp in their passports and attend the oligarch’s 2011 birthday celebrations.

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Muhammad Ali in Iraq

Float like a butterfly, sting like a diplomat? In 1990, heavyweight champ Muhammad Ali went to Iraq with the purpose of rescuing American hostages. Taken by Saddam Hussein following the invasion of Kuwait, 15 civilians were being used as human shields, placed in locations deemed likely to be bombed by American forces. Despite Hussein’s initial refusal to meet and the U.S. government’s characterization of the effort as “loose-cannon diplomacy,” Ali persevered. He worked with local media, embraced starstruck Iraqis and reiterated his determination to stay until the Americans were released. When Hussein finally agreed to meet with Ali, the boxer listened patiently while the dictator extolled his virtues. In response, Ali told him he would tell “an honest account” of Iraq. Against the odds, Hussein released all 15 Americans — solidifying the boxer’s title as the Greatest of All Time.

Photography provided by Fabio Diena/

Sting in Uzbekistan

Even though he was “well-aware of the Uzbek president’s appalling reputation in the field of human rights as well as the environment,” Sting nonetheless accepted a 2010 invitation from Islam Karimov’s eldest daughter to perform at a private event. Apparently, the singer’s commitment to his wallet is deeper than his commitment to humanity as he pocketed a reported $2 million for the performance. In defense of his actions, he claimed to believe the concert was sponsored by UNICEF, who deftly denied any such involvement. One can only wonder if the playlist that night included “If You Love Somebody Set Them Free.” 

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Angelina Jolie in the World’s Most Conflicted Countries

She might need a security team to go to Starbucks, but that hasn’t stopped Angelina Jolie from traveling to a host of dangerous places in the name of humanity. Of her time in Sudan, she wrote in the Washington Post that “nothing separates us from Darfur but a small stretch of desert and a line on a map. All the same, it’s a line I can’t cross.” At the time of her 2007 visit, the United Nations put the death toll there at 200,000, with another 2.5 million people driven from their homes. The next year, Jolie journeyed to Afghanistan on behalf of refugees returning from Pakistan after the defeat of the taliban. And just last fall, the actress made a special trip to meet with displaced Venezuelan refugees as a UNHCR Special Envoy.

Read this article as it appears in the magazine.

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