Are ‘friends for life’ Dennis Rodman and Kim Jong Un the weirdest celebrity-dictator partnership yet?

North Korean leader Kim Jong-unn, left, and former basketball star Dennis Rodman watch North Korean and U.S. players in an exhibition basketball game at an arena in Pyongyang (AP Photo/VICE Media, Jason Mojica)

Former Chicago Bull and NBA star Dennis Rodman has raised eyebrows with a gush of admiration for North Korean dictator Kim Jong Un, who he met while filming a documentary on the East Asian country.

Rodman and Kim watched a US versus North Korea basketball game sitting side-by-side and the North Korean leader was pictured smiling and laughing in the stands.

Rodman later declared Kim had a "friend for life" in a speech delivered to the thousands-strong crowd.

The friendship was cemented as before leaving Pyongyang Rodman added: "Guess what, I love him. The guy's really awesome."

This is not the first time celebrities have found themselves rubbing shoulders with leaders of undemocratic and repressive regimes:

Hilary Swank, Jean-Claude van Damme and Ramzan Kadyrov (2011)

Swank, who won an Oscar for her role in Million Dollar Baby (2004), sacked all her management staff after she and Jean-Claude van Damme were widely condemned for making a front-row appearance at a lavish party in honour of Chechen leader Ramzan Kadyrov, who presided over what many human rights organisations consider one of the most repressive societies in the world.

Both Swank and van Damme were reported to have been paid handsomely for their tribute - with the silver screen hard-man going so far as to say "I love you, Mr Kadyrov".

Sting and Gulnara Karimova (2010)

Committed eco-campaigner Sting crooned at a concert organised by the daughter of Uzbekistan's 75-year-old dictator Islam Karimov.

Britain's ex-ambassador to the region Craig Murray called the pop star's decision "incredibly stupid", though Sting, who received a £2m fee according to reports in the Uzbek media, claimed he was "well aware of the Uzbek President's appalling reputation". Karimov is alleged to have had political opponents boiled alive and openly assassinated. Sting played "in spite of that" as "cultural boycotts are...counter-productive".

Beyoncé and Muammar Gaddafi (2009)

Beyoncé received a £1.2m fee to play at a Gaddaffi family New Year's Eve concert in the Caribbean island of St Bart's, though when links to the dictator were revealed she donated the money to relief efforts in Haiti. Her reputation escaped with minimal tarring.

Naomi Campbell and Charles Taylor (1997)

After a dinner at the home of Nelson Mandela, three “small, dirty-looking stones” were delivered to Campbell by personages associated with Liberian dictator Charles Taylor. These stones were in fact most likely blood-diamonds, and Taylor was later brought to trial by the UN for war-crimes and using gems to fund rebellion in Liberia’s neighbouring Sierra Leone.

So is Rodman’s dalliance with power more or less shameful than his celebrity predecessors'? Let us know in the comments below.