Martha Stewart
Stewart is the founder of an eponymous media empire that includes magazines, TV shows, books, and serving spoons. And in case you were living under a rock in 2004, she also happens to be a convicted felon.
One of six kids born to working class Polish parents, Martha grew up in Nutley, New Jersey and ate Gulden's mustard on white bread as an after-school snack. "Marty" (as she was known then) modeled her way through high school, continuing to pose for shoots on the side when she moved to the city to attend Barnard. By the late 1960s, she was married, the mother of a young daughter and working as a stockbroker. She later quit her job to live the life of a Westport housewife. In the mid-'70s, she launched a small catering business out of her Turkey Hill Road home, which led to her first book, 1983's Entertaining. Several other books followed in the '80s—as did regular appearances on TV shows like Today—and in 1990 Time Inc. signed her up to publish a magazine, Martha Stewart Living. After buying back the magazine and other assorted media assets from Time Inc in 1997, she took the media and publishing juggernaut public on October 19, 1999, making herself an instant billionaire.
As you undoubtedly remember, Stewart was accused by the SEC of insider trading in 2003. The story in a nutshell: Federal prosecutors alleged that Martha had sold shares in the biotech company ImClone after receiving inside information from her stockbroker, Peter Bacanovic, and Sam Waksal, the CEO of the company. The stubborn Martha decided against accepting a plea bargain and challenged the government's case, which led to the most public trial of 2004; a decidedly lackluster defense by her lawyer, Robert Morvillo, resulted in Stewart being convicted of obstruction of justice. Her sentence was significantly steeper than any plea she could have negotiated: five months in prison, five months of house arrest, a $200,000 fine, and a prohibition from serving on the board (or in an executive position) at a public company for five years.
Following her indictment in 2003, Martha stepped down as CEO, handing the reigns to Sharon Patrick, a longtime business associate. Since her arrest, Martha dove back into the business with gusto. Over the past few years, she's unveiled new magazines, books, an interior paint line, and her daytime show Martha, which lasted for seven seasons until 2011. Alas, her experiment with primetime TV wasn't quite as successful: The Apprentice: Martha Stewart crashed and burned after a couple of months and Martha ended up in a war of words with Donald Trump.
Cruel, heartless, and verbally abusive, Martha has long been known as one of toughest people to work for. She's had countless falling-outs with friends and employees alike over the years. Martha divorced publishing executive Andy Stewart in 1990. But the marriage had reportedly fallen apart several years earlier as Martha became increasingly obsessed with her emerging empire (and as Andy started cheating with other women, including author Erica Jong). They have one daughter together, Alexis. Martha's dated a handful of men since her divorce. Most recently, she had an on-again, off-again relationship with Microsoft billionaire Charles Simonyi, who dispatched his plane to pick her up when she was released from prison. A nice gesture, though they broke up shortly thereafter. [Image via Getty]