Martha Stewart

Before the magazine empire, there was a basement catering operation in Westport, Connecticut. She'd already worked as a stockbroker on Wall Street, but the 1982 cookbook Entertaining was the real pivot: a glossy, opinionated guide to hosting that treated homemaking as a professional skill worth taking seriously. A Kmart merchandise deal and the Martha Stewart Living Omnimedia IPO in 1999 followed, briefly making her the first female self-made billionaire in the United States. She built an aesthetic monopoly before anyone had a word for personal branding.

In 2004, she was convicted on four counts: conspiracy, obstruction, and two counts of making false statements to investigators. Not of insider trading itself, just of pretending it never happened. She reported to Alderson Federal Prison Camp in October 2004 and was out by March 2005. The comeback didn't happen slowly: her company sold to Sequential Brands Group in 2015 for $353M, and well into her eighties, she's releasing Netflix documentaries, publishing her 100th cookbook, and co-hosting NBC competition shows. Her brand survived prison better than most brands survive a bad quarter.

As a teenager in Nutley, New Jersey, she babysat for Mickey Mantle, Yogi Berra, and Gil McDougald. She dated Anthony Hopkins and reportedly ended things after watching him eat someone in The Silence of the Lambs. Finding Your Roots later confirmed she's a distant cousin of Jimmy Kimmel through DNA testing, which neither of them seems particularly excited about. She reportedly sleeps four hours a night with the lights on. The homemaker image was always a front for something considerably more ruthless.