The queen of home decor and lifestyle, Stewart spent five months in prison for insider trading in 2004.
The former CEO of Tyco International served over six years for his involvement in a scandal involving unauthorized bonuses and loans.
Once the head of WorldCom, Ebbers was convicted of orchestrating an $11 billion accounting fraud scheme and was sentenced to 25 years.
Former Enron CEO Skilling was convicted of conspiracy, fraud, and insider trading related to the company's collapse, serving over 12 years.
The media magnate behind Hollinger International spent more than three years in prison for fraud and obstruction of justice.
As the former head of McKinsey & Company, Gupta served two years for insider trading involving Goldman Sachs.
The real estate mogul was convicted of price-fixing and spent nearly a year in prison.