5) Enron

5) Smartest guys in the cell

Enron once called itself the most innovative company in America.

But executives there were probably most groundbreaking in cheating investors. In 2001, Enron, an energy company that also provided broadband and streaming media services, created offshore companies that were essentially trash containers. Enron hid losses by shifting them to these dummy firms.

Investors, many of them Enron employees, were left holding the bag as the stock plummeted from $90 per share to pennies. Most of the company's top managers went to jail, except Ken Lay (left, top), the company's chairman, who died before serving time.

Jeff Skilling, Enron's former CEO (left below), was sentenced to 24 years in prison. The once swaggering exec was interviewed recently by Fortune magazine: "Could you buy me a cup of coffee?" Skilling asked the reporter. "Inmates aren't allowed to touch money."