Anne Hathaway and Raffaello Follieri
Sometimes the devil wears Armani. The actress, 25, and Italian real estate developer, 30, started dating in 2004 and living la dolce vita off Follieri's business dealings. They broke up in June, just before Follieri was arrested and accused of lying to investors by claiming to be the CFO of the Vatican and swindling funds, for, among other things, the $37,000 monthly rent for their Fifth Avenue apartment. Follieri pleaded guilty in September to 14 counts of wire fraud, money laundering and conspiracy, and was sentenced to four and a half years in prison. Hosting Saturday Night Live in October, Hathaway poked fun at the incidents, saying, "I broke up with my boyfriend, and two weeks later he was sent to prison for fraud. I mean, we've all been there, right, ladies?"