Martha Stewart's Transformation Is Really Turning Heads

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It's apropos that Martha Stewart's first magazine was called Living. The world's original self-made female billionaire has done plenty of it, starting out as a girl from the suburbs who modeled to put herself through school and now, at 80, an eponymous media and consumer brand that, according to Forbes, reaches 100 million people a month, 70 million of whom have Martha Stewart products in their homes. But her journey along the way has been anything but simple.

Stewart's changed course more than once, having to start over personally after her 26-year marriage imploded, and professionally, amidst scandal, after being convicted of financial crimes that landed her a five-month sentence in federal prison. Time and again, she reinvented herself: going from disgraced ex-con to cultural icon; from domestic network goddess to Snoop Dogg's best gal; and from a buttoned-up homemaker to the horniest octogenarian you're likely to swipe right on. Tipping our hat to a woman who continues to surprise us, we take a look back at Martha Stewart's many transformations over the years.

Martha Stewart started modeling to pay for college

Growing up in Nutley, New Jersey in the 1950s, a young Martha Stewart (Martha Kostyra back then) had aspirations to go to a good college, but needed to find the means. A natural looker with poise to spare, she began modeling to pay her way through New York's prestigious Barnard University. "I was one of six kids and two working parents," she shared with Today's" Jill Martin. "We were taught to work, we were encouraged to pay our own way, and we all did."

She was far from the average catalog mannequin. In her modeling heyday, Stewart shot campaigns for Clairol and posed in haute couture for Chanel. She made up to $50 an hour, which was a pretty nice income at the time. And she's been taking care of business ever since, proudly telling fellow mogul Oprah Winfrey she relishes "a feeling that I can write a check without worrying, choking, or fretting. And that's how I've always approached my jobs. There had better be a pot of gold at the end of the rainbow, because [getting there] is really hard."

Martha Stewart was once a stockbroker

A little-known fact about Martha Stewart: a lot of her business savvy comes from the seven years she spent as a New York stockbroker. After marrying husband Andrew Stewart in 1961, she reportedly took advice from his father and got a job working downtown at the stock market. Unsurprisingly, Stewart was a whiz with numbers. But as the only woman at her firm in what was still a very male-dominated industry, she had to fend off plenty of unsavory advances.

"You saw the movie 'Wall Street'?" she commented to Harper's Bazaar in a recent profile. "I lived it. I mean, every man on Wall Street was trying to get you. Every man was trying to touch you in the cab. We had martinis for lunch." As always, however, Martha kept her eyes on her paper. "I did not," said firmly, "f*** around, if you want to use that word. You had to keep your cool and just do your thing, and brush them away." Nearly four decades later, a poor stock-trading decision in 2001 led to Martha Stewart's infamous financial scandal, landing her in federal prison. But more on that in a minute.

Martha Stewart became a mom at 24

In 1965, Stewart gave birth to her only child, her daughter Alexis. And while she's built her empire as an expert of the home, Stewart's own household was surprisingly cold, unfun, and fraught with tension, according to her kid. In a 2011 book entitled "Whateverland: Learning to Live Here," Alexis Stewart describes a stressed-out childhood scarred by her mother's lack of caring. She grew up with no Halloween costumes, no snacks, and the constant pressure of perfectionism, Alexis claimed. Perhaps most shocking of all, she alleged that Martha Stewart used to pee with the door open when there was company over.

It was dirty laundry for sure, but Martha Stewart, as always, took it in stride, noting that Alexis, by then a mom herself, had turned out just fine. "I must have instilled in her some good habits," she remarked on her daytime talk show. "She's tall, beautiful, gorgeous and mother of baby Jude and that's all that counts." In recent years, mother and daughter appear to have reached a mutual understanding. Speaking to People in 2020, Stewart shared that while their relationship has always been difficult, she knows Alexis " would do anything for me, and I would do anything for her."

At a career crossroads, Martha Stewart tried catering

Disillusioned with the big city, Stewart and her family moved to the Connecticut suburb of Westport, purchasing a farmhouse complete with its own barn. She had grown tired of Wall Street but wasn't sure what to do next. Stewart had spent years entertaining clients and used this experience to transition to a catering business. After placing an ad in a local paper, Stewart then found herself "preparing blindly for a wedding for 300," per Entrepreneur.

We all know how that turned out. Stewart ended up launching her first company, the Uncatered Affair, and setting up a local prepared food shop called the Market Basket. Through contacts, she was tapped to write magazine columns, then, in 1982, she released her first cookbook, "Entertaining." Following its release, several critics accused her of lifting her recipes, an allegation that continued to follow her for years. True to form, Stewart brushed it off. "I don't know why, as a cookbook author, I have to be so controversial," she reportedly stated. "I'm writing beautiful books that bring so much good and enjoyment to people — what's wrong with that?"

Martha Stewart had an ugly divorce

While her career flourished, Stewart's personal life soured over the next few years. And in 1987, Martha and Andrew Stewart split. Far from an amicable separation, it was a tawdry affair. Andrew Stewart sought a court order preventing his estranged wife from even speaking to him, People reported. Adding insult to injury, he began seeing her former assistant, who he ended up marrying in 1993. Martha Stewart did keep his last name, which, by then, had become an essential part of her image. But everything else about the union, she left in the dust. She says has not spoken to her ex-husband since. "The life that I had is over," she later said in a 1995 People interview. "And what has taken its place is better."

Stewart never remarried and has since kept her relationships relatively private. She dated actor Anthony Hopkins in the 1990's but joked she couldn't get past his frightening portrayal of Hannibal Lecter in "Silence of the Lambs." She moved on to billionaire Charles Simonyi, her beau for the next 15 years before their reported 2008 breakup. More recently, she's joined, but made it clear she's probably too busy to tie the knot again. 

Martha Stewart makes her TV debut, launching her longtime on-air career

Stewart's career ascended quickly, with her first magazine, Martha Stewart Living, hitting stands in 1990. Two years later, she jumped from the page to the airwaves, launching her first television show, "Martha Stewart Living TV," as a syndicated series. In each episode, Stewart took viewers through the basics of finer home care –  including cooking demonstrations, decorating tips, and creative entertaining ideas. It solidified her role as America's domestic connoisseur, a title she says she's never approached lightly. "I think baking cookies is equal to Queen Victoria running an empire," she told Oprah. "There's no difference in how seriously you take the job, how seriously you approach your whole life."

She amassed a loyal fan base who tuned in regularly for her expertise. Ten years later, her show was snapped up by the Hallmark Channel, which blocked off over two hours each weekday for original Martha Stewart programming, along with daily repeats. Two years after that, however, Hallmark canceled the series, citing its high production costs. (What, like you thought working with her was cheap?) Without missing a beat, Stewart took her show to PBS, but couldn't resist a little shade on her way out, dissing the cable network by saying that, "easy access to PBS as opposed to Hallmark will be wonderful."

Martha Stewart became the first female self-made billionaire

Kylie who? Years before anyone heard of the Kardashian-Jenner clan, Martha Stewart made history as America's real first self-made female billionaire. In 1999, she took the conglomerate she had formed, Martha Stewart Omnimedia, and went public, instantly tripling her net worth and earning her $1.6 billion with the opening ring of the stock market bell. Her only regret, she later told Business Insider, was not taking a minute to go on a well-deserved shopping spree and pick herself up a thing or two.

"That was a great day," she reflected. "I drove up Madison Avenue after the offering. I was an instant $1.6 billionaire. It was a fabulous day and I thought, huh ... I can buy anything on this street! And I shoulda stopped! Like at every art gallery on the way up Madison Avenue, and just bought what I loved. But I was too busy working." A year later, she did treat herself to a $15.2 million,152-acre home in Katonah, New York where she now rubs elbows with neighbors Blake Lively and Ryan Reynolds. According to records, the expansive property features several structures where Martha lives, works, and entertains.

One phone call turned Martha Stewart into a convicted felon

Martha Stewart's world came crashing down when New York state prosecutors learned of a December 2001 tip she received about the pending approval of a new cancer medication. Told by the company's founder that the FDA was set to decline the medication's approval, Stewart allegedly dumped her stock. In the eyes of the law, that's considered insider trading, a crime that she, her stockbroker, and the medical company's founder were all later charged with. Still, Stewart expressed doubt a judge would actually throw the book at her.

She thought wrong. Convicted of all four charges, she was sentenced to five months in prison, followed by five additional months of home confinement. The world was shocked and the national headlines blared: the celebrated face of American home etiquette was headed to the clink. While also forced to step down from the board of her company, Stewart solemnly proceeded with her punishment, requesting to begin her prison sentence immediately in order to "put this nightmare behind me." On a lighter note, once behind bars, Stewart was reportedly quite a popular felon. She took interest in her fellow inmates, showing them how to make the most of their meals and teaching them ceramics. Her self-awareness was also affected, her lawyer told the press. "She's achieved a certain kind of serenity," he said. "She didn't used to listen much. She knew what she should do and went about it. Now she listens."

Martha Stewart made her comeback with a competition show

Once done with her prison sentence, Martha Stewart's career was a bit radioactive — and it took several years for her to get back on her feet. It was Donald Trump, of all people, who gave her a fresh start, offering her a spinoff of his hit reality competition show, "The Apprentice." The 2005 version — "The Apprentice: Martha Stewart" — not only put her back in the public eye, but it also offered a friendly, more accessible version of her old self. The New York Times called it a refashioning of her persona "from steely business diva to cheery, chatty gal pal." She even poked fun at her time in the slammer, demonstrating some of the prison dishes she whipped up while behind bars.

She wasn't the only person to benefit from the show's success. A then-unknown aspiring chef named Bethenny Frankel placed second. After being cast on "The Real Housewives of New York," Frankel is now arguably the most successful star the Bravo franchise has ever seen, reportedly selling her Skinnygirl liquor and food brand for a reported $100 million. In 2013, the relationship came full circle when it was Stewart's turn to appear on Frankel's daytime television talk show. "You were a pest," Stewart teased. "And now you can be that. You're the host."

Martha Stewart became queen of the clapback

Martha Stewart's cheeky new persona really got people talking at the 2015 Comedy Central Roast of pop star Justin Bieber. To pretty much everyone's surprise, Stewart more than held her own. She was, in fact, the unexpected hit of the night. Poking fun at both her own time in prison and Bieber's own recent run-ins with the police, she dryly told him: "I've been in lockup and you wouldn't last a week." She also took aim at others onstage, ripping comedian Natasha Leggero for a promiscuous reputation and referring to Hannibal Burruss "the gingerbread man I left in the oven too long,"

Overwhelmingly reviewers loved it. And to everyone's enjoyment, her shade of fellow celebrities has made headlines ever since. She dismissed Rachael Ray as an entertainer and has taken several swipes at Gwyneth Paltrow and her lifestyle brand GOOP, calling her a wannabe, telling her to stick to acting, and giving a thumbs down to her products. Even when GOOP's vagina-scented candle sold out, Stewart made it clear she was wholly underwhelmed. "Let her do her thing," she sniffed. "I wouldn't buy [it]."

An unlikely friendship gave Martha Stewart new street cred

One celebrity she did it hit off with? None other than the Doggfather. Stewart and Snoop Dogg struck an unlikely friendship back in 2008, during Snoop's first appearance on her former daytime talk show. Flattery was traded over the years through events, interviews, and social media, and in 2016, they finally came together for the VH1 series, "Martha & Snoop's Dinner Party." Called a "national treasure" by Eater, the loosely formatted series showcased the star duo hosting dinner for various celebrities. Sometimes they'd cook, sometimes they'd eat. Most of the time, they drank cocktails, got their buzz on, and bantered.

Not only was the show a delight, but the friendship also opened a new revenue stream for Martha Stewart. Her friend Snoop, after all, a notorious toker, sparked her interest in the cannabis industry and inspired her new line of CBD products. As for Snoop, he's bragged that Stewart is tougher than some of the biggest rappers on the street. Apparently unimpressed with the antics of Tekashi 6ix9ine, who won his freedom from prison by ratting out his co-conspirators, Snoop reminded everyone via Instagram, "to remember Martha Stewart snitched on NOT ONE SOUL during her trial. Baby Girl kept it 10 toes down and ate that prison sentence by herself like the true baddie she is."

At 78 years old, one Instagram post photo turned Martha into a thirst trap

Who needs Tinder when you've got nearly four million followers? And with one 2020 Instagram post, Martha Stewart let everyone know she was truly feeling herself. Sure, the post talked about her new swimming pool's paint job, but the real message was clear: Martha Stewart is most definitely a snack. The snap obviously went viral, with fans commenting that it was Martha's Stewart's hot girl summer, indeed.

Stewart herself played coy, claiming the smoldering selfie had been accidental. "I was actually trying to take a picture of the beautiful planted pot at the end of my pool, and I must have hit the reverse button on my camera," Stewart later said on "The Drew Barrymore show." "And there I am in the picture, and I snapped it and said, 'boy you look really good!' and that was that." The pic resulted in no less than 14 marriage proposals, she also shared with E! News. But as she's made clear, when it comes to settling down, Martha Stewart just ain't got the time.