Lou Pearlman
The Svengali behind the '90s boy-band juggernaut, Lou Pearlman was not the jolly music mogul he painted himself to be. After a failed career in aviation, Pearlman turned an eye to the entertainment industry. He set out to create other boy bands in the model of New Kids on the Block, which he did to great success, creating the wildly popular Backstreet Boys and 'NSYNC, as well as O-Town and solo pop star Aaron Carter. However, many of those acts went on to sue Pearlman for misrepresentation and/or fraud. But the most egregious claims levied against Pearlman came to light in 2006, when it was discovered that he had perpetrated an elaborate Ponzi scheme, defrauding investors to the tune of $300 million by creating an airline and airline service company which did not exist. He tried to flee, but was caught on the run in Indonesia and brought to court. In 2008, Pearlman said "bye bye bye" to his lavish lifestyle when he was convicted of conspiracy and money laundering and sentenced to 25 years in prison.