Oprah Winfrey turned her weight-loss journey into a business. Here’s how her health empire has evolved.

Winfrey wrote about a specific incident she recalled with Joan Rivers in her 2017 cookbook, “Food, Health and Happiness,” which was excerpted on Oprah.com.

After winning Miss Black Tennessee in 1971, Winfrey gained 42 pounds in 15 years. It was something that Rivers, who was guest-hosting a 1985 episode of “The Tonight Show,” was quick to point out when Winfrey was a guest.

“It was all going smoothly,” Winfrey wrote. “I was starting to settle in. And then it happened: Joan interrupted with perhaps the only question I hadn’t prepared for: ‘So how’d you gain the weight?'”

“The studio started spinning. The word fat…fat…faaaaatttttt reverberated in my brain,” Winfrey continued.

“It was a public sport to make fun of me for 25 years,” Winfrey told People in 2023.

During a 1988 episode of “The Oprah Winfrey Show” — a few years after Joan Rivers asked about Winfrey’s weight gain — Winfrey wheeled out a red wagon filled with 67 pounds of animal fat.

Why? To convey to her audience how much weight she’d lost in the last year while on the Optifast liquid diet.

The episode put a spotlight on medically supervised liquid formula diets. After it aired, The New York Times reported that Winfrey got just 400 calories a day from Optifast and wrote that the ability of people on such diets “to maintain the loss is questionable and not yet fully evaluated.”

For a 2005 issue of O, The Oprah Magazine, Winfrey wrote, “For four solid months, I didn’t eat a single morsel of food,” and lost 67 pounds. “What I didn’t know was that my metabolism was shot. Two weeks after I returned to real food, I was up 10 pounds.”

While she was proud of losing the weight, Winfrey later regretted the decision to pull the wagon out.

“When I look at that show, I think it was one of the biggest ego trips of my life,” Winfrey told Entertainment Tonight in 2011.

She cowrote “Make the Connection: Ten Steps to a Better Body and a Better Life” with exercise physiologist (and her personal trainer) Bob Greene.

The 10 steps included guidance such as “exercise 20 to 60 minutes a day,” “eat a low-fat, balanced diet,” and “eat three meals and two snacks each day.”

It went on to become a No. 1 bestseller and is still in circulation.

Winfrey introduced audiences to Phil McGraw, aka Dr. Phil, in the late ’90s as her show’s resident relationship expert. He proved so popular that Winfrey produced and co-created a spinoff of “The Oprah Winfrey Show” starring McGraw: “Dr. Phil.” It aired from 2002 to 2023, and for most of its run, it was second in ratings only to Winfrey’s show.

Like Winfrey, McGraw frequently discussed weight loss and health on his show, and also lent his face and name to nutritional supplements. As The New York Times wrote in 2003, “Oprah Winfrey has talked about weight loss — hers and everyone else’s — for years. Her protégé Dr. Phil has found a way to make money from it.”

He’s also written his own weight-loss books, including “The Ultimate Weight Solution: The 7 Keys to Weight Loss Freedom” and “The Ultimate Weight Solution Food Guide.”

Winfrey also introduced Dr. Mehmet Oz to her show’s audience. He made his “Oprah” debut in 2004 and ultimately appeared more than 60 times, per NPR, before Winfrey greenlit “The Dr. Oz Show” in 2009. It aired until 2022, when he began a US Senate campaign in Pennsylvania.

Similarly, Oz’s program featured many segments on weight loss, and Oz himself endorsed multiple “cures” for obesity that have been disproven. He was appointed administrator of the Centers for Medicare & Medicaid Services in 2024.

While it’s not known how much money Winfrey made from their two shows, both aired for over a decade (with reruns on Winfrey’s channel, OWN), and Winfrey’s production company, Harpo Productions, was involved throughout.

Winfrey’s own show, which aired for 25 years, was the foundation of her wealth, rocketing her to millionaire status when it became nationally syndicated in 1986. By 2003, she was a billionaire, and she’s now worth an estimated $3.2 billion, Forbes reported.

In 2015, Winfrey announced she was joining the board of WeightWatchers (now known as WW International, or WW) and was purchasing a 10% stake in the company worth $43 million.

The New York Times reported in 2015 that it led to an increase of $400 million in market value for the brand, which had been trending downward before Winfrey’s involvement.

“WeightWatchers has given me the tools to begin to make the lasting shift that I and so many of us who are struggling with weight have longed for,” she said in a statement. “I believe in the program so much I decided to invest in the company and partner in its evolution.”

It’s an example of the Oprah Effect: the trend of Winfrey endorsing, supporting, or investing in a brand that leads to a spike in value.

Winfrey posted on X (then Twitter) a video about how she’d lost 26 pounds on WeightWatchers while still eating bread.

“I love bread,” she said. “That’s the genius of this program. I lost 26 pounds, and I have eaten bread every single day.”

According to MarketWatch, the subsequent bump in the stock price, just one hour after the post, netted Winfrey around $12 million.

Winfrey’s cookbook, which also reached bestseller status, incorporated the WeightWatchers system into its recipes and flagged the number of points each meal was worth, in a neat bit of corporate synergy.

In 2020, Winfrey traveled the US on a speaking tour sponsored by WW called “2020 Vision: Your Life in Focus Tour,” in what turned out to be a highly lucrative move. Billboard reported the tour made $18.8 million.

Each stop featured a celebrity guest, including Tina Fey, Michelle Obama, and Jennifer Lopez.

The tour “has driven strong performance in member signups year-over-year,” said Mindy Grossman, then the president and CEO of WW.

“Member recruitment so far in 2020 has been well above the prior year,” added then-CFO Nick Hotchkin.

Winfrey told People about her journey with weight-loss medications, saying, “I eat my last meal at 4 o’clock, drink a gallon of water a day, and use the WeightWatchers principles of counting points. I had an awareness of medications, but felt I had to prove I had the willpower to do it. I now no longer feel that way.”

At the same time, WeightWatchers itself began embracing GLP-1s. Then-CEO Sima Sistani told NPR, “It’s really important that we acknowledge that there has been a decadeslong narrative that has painted weight loss as a mere test of willpower, and it’s perpetuated this sense of shame and misunderstanding around what it means to live with overweight and obesity. So for some, different solutions like these new clinical interventions are really needed.”

WeightWatchers announced its own GLP-1 business the next day, per Market Beat, and shares rose 10%.

Soon after confirming her use of a GLP-1, Winfrey publicly said she wouldn’t be seeking reelection to the board.

The announcement sent WeightWatchers’ stock tumbling 25%. As Business Insider wrote at the time, it seemed like Winfrey was jumping ship from an “outdated operating system” in the age of Ozempic and other GLP-1s.

Winfrey’s latest book, “Enough,” which she cowrote with Dr. Ania M. Jastreboff, was released in January 2026. It details Winfrey’s experience with GLP-1s, combined with Jastreboff’s expertise.

Winfrey has been promoting her book heavily, including a stop on “CBS Sunday Morning,” where she explained how reframing her relationship to obesity and weight has changed her life.

“I’m not going to, but I could weep right now for all of the many days and nights I’ve journaled about this being my fault and why can’t I conquer this thing?” she said.

“There are tools to use that can help you. And I do see [GLP-1s] as a tool,” she continued.