Embarrassing Embraces

A Western leader might break off a relationship with a despot, but no one can erase the snapshots of them together in happier days. From Bush holding hands with the Saudi king to Obama chatting up Hugo Chavez, see photos.

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Kim Jong-il and Madeleine Albright

Now that’s diplomacy. Kim Jong-il and U.S. Secretary of State Madeleine Albright toast in Pyongyang in 2000. Chances are there next words were not, “Let’s get crunk.”

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George W. Bush, Bill Clinton and Hosni Mubarak

Hosni Mubarak was a valued ally of U.S. administrations from Reagan to Obama, who tolerated his authoritarian regime in return for a stable, Western-friendly relationship. Here, Clinton shares a moment with the Egyptian in 1993, and Bush chauffeurs Mubarak around at Sharm el-Sheikh in Egypt in 2003 (Bush's pal King Abdullah rides in the back).

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Muammar Gaddafi and Silvio Berlusconi

Libya's Muammar Gaddafi and Italy's Silvio Berlusconi formed a particularly close bond in recent years. Both are outsize personalities who dislike accountability and share an affinity for the fairer sex. But now that Gaddafi is persona non grata in the international community, Berlusconi may regret this 2009 picture, in which he appears to be making a move on his friend, regardless of homophobic comments he's made.

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Tony Blair and Muammar Gaddafi

Tony Blair has described his backing for the war in Iraq as a humanitarian move, but he didn't call for the overthrow of every dictator. Here he shares an intimate moment with Gaddafi in 2007—a particularly embarrassing photo op given British anger at Gaddafi over the Lockerbie bombing.

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George W. Bush and King Abdullah

In the Middle East, handholding between men is a common gesture of friendship. But when President Bush walked hand-in-hand with the Saudi king at his ranch in Texas in 2005, it caused a few tongues to wag.

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Barack Obama and King Abdullah

Bush doesn't have a monopoly on embarrassing snapshots with the Saudi monarch. In April 2009, Obama greeted Abdullah at Buckingham Palace with what some observers took to be a bow. After howls that Obama was humbling the U.S. before Saudi Arabia, the administration claimed he was just accommodating the shorter king.

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Jimmy Carter and the shah of Iran

Cheers? Any happiness would dissipate soon after this 1977 Tehran meeting between Mohammad Reza Shah Pahlavi and Carter. The U.S. backed the pro-Western Pahlavi despite his brutal handling of internal opposition. When anger boiled over in 1979, Pahlavi was deposed, bringing a radical Islamist government to power in Iran and humiliating Carter.

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Barack Obama and Hugo Chavez

One might imagine Venezuelan President Hugo Chavez as that guy at the party who tries to corner you into a conversation about his pet conspiracy, but President Obama actually sought Chavez out for a brief and cordial handshake and introduction at a summit in Trinidad in April 2009.

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Nelson Mandela and Muammar Gaddafi

Mandela's name has become practically hallowed, but his roots—as a young militant African revolutionary—aren't far from Gaddafi's. Here, the two men hug as Mandela arrives in Tripoli for a 1990 visit.

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Leonid Brezhnev and Erich Honecker

The relationship between Moscow and East Germany was always intimate, but when Soviet leader Leonid Brezhnev (right) visited East Berlin to be honored as a "hero of the German Democratic Republic" and receive the Karl Marx Medal, he and East German leader Erich Honecker got especially intimate in this nearly lick-locking moment.

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Fidel Castro and Richard Nixon

Although the U.S. backed Fulgencio Batista, the man Castro overthrew, we didn't leap immediately to assassination attempts and failed invasions. Castro even visited the U.S. in April 1959, shortly after coming to power. He met with then-Vice President Richard Nixon. The two spoke for more than two hours longer than scheduled, and Castro called the encounter "very friendly."

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Josef Stalin, Franklin D. Roosevelt, Winston Churchill

Desperate times call for desperate measures—including allying with bloody dictators. During World War II, Roosevelt and Churchill met with Stalin more than once, including this meeting in Tehran in 1943. Within five years, the U.S. and USSR would be locked in the Cold War and Churchill would be warning of an "Iron Curtain."

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Donald Rumsfeld and Saddam Hussein

In 2003, Rumsfeld led the Bush administration's push to topple Hussein. But in 1983, the former secretary of defense was in Baghdad and shaking hands with the dictator, whom the U.S. was supplying with weapons in his war against Iran.

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2009 G-8 Summit

There's one in every group, isn't there? At the 2009 G-8 summit in L'Aquila, Italy, Dmitry Medvedev of Russia, President Obama, and U.N. Secretary-General Ban Ki-moon stood awkwardly, listening as Gaddafi orated prior to a moment of silence for the victims of a recent earthquake. Berlusconi and France's Nicolas Sarkozy, however, looked somewhat amused.