20. A Creepy Womanizer
Gaddafi was creepy. He had a habit of hitting on female reporters, often meeting them for interviews in bathrobes or in his underwear. He also became obsessed with former US Secretary of State Condoleeza Rice, referring to her as his “darling black African woman“. When she visited Tripoli, Gaddafi showered her with over $200,000 worth of gifts, including a lute and a locket with his picture inside.
Gaddafi also saw himself as a fashion icon, and to that end cultivated an odd collection of ensembles and sartorial choices that made him modern history’s most bizarrely dressed ruler. Changing in and out of silly uniforms multiple times a day, he was the closest real life depiction of a James Bond villain. The cartoonish villain look was further enhanced by his all-virgin female bodyguard, officially named the “Revolutionary Nuns”, but known more commonly as the Amazonian Guard.