The Highs and Lows of Oprah Winfrey's 50-Year Weight Loss Journey

One of our favorite things through the years has been Oprah Winfrey's honesty about her own weight loss journey.

By Natalie Finn Mar 24, 2024 12:00 PMTags
Watch: Oprah Winfrey Addresses Her Use of Weight Loss Drugs & Decades of Shaming

Among the many things Oprah Winfrey is the queen of—talk shows, interviews, book clubs, favorite things—she has also been a leading voice in the weight loss space.

Not because she has all the answers, as she'd be first to admit.

But because the 70-year-old billionaire has been talking about her own fluctuating weight for as long as she's been in the public eye.

From rolling out a wagon loaded with 67 pounds of jiggly fat to wow her Oprah Winfrey Show audience in 1988, to buying a stake in WeightWatchers in 2015 and hosting a March 18 primetime special examining where society's at when it comes to this ever-relatable yet still taboo subject, Winfrey has used her platform to keep the conversation going.

While sometimes the discourse has been as benign as Winfrey declaring her unabashed love of bread, she has also ventured into some dark places. And most recently, she took on the topic du jour.

Fascinating Facts About Oprah Winfrey

"In my lifetime I never dreamed we would be talking about medicines that would be providing hope to people, like me, who have struggled for years with being overweight or with obesity," she said on An Oprah Special: Shame, Blame and the Weight Loss Revolution, addressing the increasing popularity of weight loss drugs such as Ozempic. "I come to this conversation with the hope that we can start releasing the stigma and the shame and the judgment—to stop shaming other people for being overweight or how they choose to lose or not lose weight—and more importantly to stop shaming ourselves."

As her loyal fandom knows, she speaks from experience.

John Salangsang/Variety via Getty Images

"I still hate myself because of my weight," Winfrey said on her eponymous show in 1986. In a later sit-down, she described her defeatist mindset: "All the fame and the success doesn't mean anything if you can't fit into the clothes. If you can't fit into your clothes, it means the fat won. It means you didn't win."

Along the way she tried seemingly every fad diet before ultimately zeroing in on her complicated relationship with food.

"I've never liked the term 'food addict,'" Winfrey said on her show in 2010, noting that she had referred to herself that way "casually" over the years. "But I realize that I really have been one. And believe me, I—like so many of you—have punished myself for that. But I know that I'm not alone, and I know that the battle hasn't ended."

A battle she acknowledged she'd been fighting every day of her life, often in public with an audience of millions wondering which size jeans she'd turn up in next, but also privately, cloaked in self-loathing because she thought she'd failed.

Stars Who Have Sounded Off on Ozempic

"All these years I thought all of the people who never had to diet were just using their willpower and for some reason stronger than me," Winfrey said in her special. "And now I realize, y'all weren't even thinking about the food. It's not that you had the willpower—you weren't obsessing over it, that's the big thing I learned."

Taking medication (she has never named which one) to help regulate her weight, along with eating smaller portions and staying active—"It's not just one thing, it's multiple things"—has changed her entire outlook.

"When I tell you how many times I have blamed myself," Winfrey added, "because you think, I'm smart enough to figure this out, and then to hear all along it's you fighting your brain."

Even though she's spelled it out every which way, it's still difficult to think of Winfrey—so beloved for her unbridled enthusiasm and sought out as a voice of reason on everything from relationships and shopping to U.S. politics and the British monarchy—as being this vulnerable.

But as everything she's shared over the years proves, the struggle has been real. Read on for a closer look at Winfrey's weight loss journey: 

Getting on the Ride

"I still have the check I wrote to my first diet doctor—Baltimore, 1977," Oprah Winfrey wrote in a 2002 essay for O magazine. "I was 23 years old, 148 pounds, a size 8, and I thought I was fat. The doctor put me on a 1,200-calorie regimen, and in less than two weeks I had lost ten pounds (there's nothing like the first time...). Two months later, I'd regained 12. Thus began the cycle of discontent, the struggle with my body. With myself."

She did all the de rigueur diets—Atkins, Beverly Hills, Scarsdale, Cabbage Soup, Banana, Hot Dog (wait, we have questions)—while having no idea "I was starving my muscles," she wrote, "slowing down my metabolism, and setting myself up to gain even more weight in the end."

The Wagon

The Oprah Winfrey Show hit a new high in viewership on Nov. 15, 1988, when the host walked onstage pulling a wagon loaded with 67 pounds of gloppy animal fat, a visceral representation of the 67 pounds—as of her weigh-in that very morning—she had lost while on a liquid diet for four months. She showed off her trim 145-pound figure in tightly belted, size-10 Calvin Klein jeans and a sleek black turtleneck.

The episode was called "Diet Dreams Come True."

The reality was something else.

"In an effort to combat all the shame, I starved myself for nearly five months and then wheeled out that wagon of fat that the internet will never let me forget," she reminisced on An Oprah Special: Shame, Blame and the Weight Loss Revolution, which aired March 18. "And after losing 67 pounds on a liquid diet, the next day—the very next day—I started to gain it back."

The Inevitable

Exactly a year later, Winfrey said on her show that she had gained back 17 pounds of the 67 she lost.

"I thought I was cured," she told People in 1991 of her crash diet and big reveal. "And that's just not true. You have to find a way to live in the world with food."

She declared on the Jan. 14 cover, "I'll never diet again!"

Meeting the Right Guy

In 1992, the 5-foot-7 Winfrey reached 237 pounds, which she has since referred to as her "heaviest" point. But it was around this time that she met trainer Bob Greene.

"When I first met Bob and he asked me why I was overweight, I thought he was being a smart-ass," Winfrey wrote for in 2007. "I was overweight for the same reason everybody else is, I answered smugly. I loved food." After "many conversations" with Greene, however, she realized she was using food to "numb my negative feelings."

She noted that she had never seen a psychiatrist, but working with Greene was "priceless therapy."

They coauthored the 1996 book A Journal of Daily Renewal: The Companion to Make the Connection, about staying in touch with your body's needs.

Still, it was easier said (and written down) than done.

"Around 1995, after years of yo-yoing, I finally realized that being grateful to my body, whatever shape it was in, was key to giving more love to myself," Winfrey wrote in 2002. "Although I'd made the connection intellectually, living it was a different story."

The Epiphany

Winfrey revealed in the 2002 essay that she had a wakeup call on Dec. 19, 2001, when—after experiencing heart palpitations for six months—she wrote in her journal that "'having palpitations at night makes me more aware of being happy to awaken in the morning, more grateful for each day.'"

She realized she'd never made really taking care of herself a priority. "For so many years," she recalled in O, "I had let my heart down by not giving it the support it needed. Overeating. Overstressing. Overdoing. No wonder when I lay down at night it couldn't stop racing."

One morning soon after, she got up and made a vow to "love my heart." Winfrey gave herself a good once-over and "though there was plenty of room for improvement," she wrote, "I no longer hated any part of myself, including the cellulite."

The Pendulum Swings

Winfrey appeared on the January 2005 cover of O to proudly announce she weighed a "toned" 160 pounds.

"I thought I was finished with the weight battle," she wrote in the magazine four years later. "I was done. I'd conquered it. I was so sure, I was even cocky. I had the nerve to say to friends who were struggling, 'All you have to do is work out harder and eat less! Get your 10,000 steps in! None of that starchy stuff!'"

But in February 2007 she started to have health issues that made exercise seem less and less appealing. Her weight started to creep back up. She was diagnosed with hyperthyroidism (which "can speed up metabolism and cause weight loss," she wrote, "but of course didn't make me lose a single pound"), followed by hypothyroidism, which tends to do the opposite.

"My doctor prescribed medication and warned me that I must 'learn to embrace hunger' or I would immediately gain weight," Winfrey wrote. "Believe me, no part of me was prepared to embrace hunger."

It took time to rebalance her life, and she gained 40 pounds—a point she illustrated when she appeared on the January 2009 cover of O, superimposed next to the 2005 version of herself.

"How did I let this happen again?" read the cover quote.

"What I've learned this year is that my weight issue isn't about eating less or working out harder, or even about a malfunctioning thyroid," Winfrey explained in the magazine. "It's about my life being out of balance, with too much work and not enough play, not enough time to calm down. I let the well run dry."

She continued, "Here's another thing this past year has been trying to teach me: I don't have a weight problem—I have a self-care problem that manifests through weight."

Win-Win Opportunity

When WeightWatchers called Winfrey (not for the first time) in July 2015 to see if she wanted to work with the business, she had gained 17 pounds while nursing a sprained ankle for a month, according to the New York Times. She subsequently bought a 10 percent stake in the company for $43 million.

And in January 2017, Winfrey announced she had lost 42 pounds working the program. (Meanwhile, WeightWatchers reported four straight quarters of revenue growth.)

By then, however, the internet had another take on her journey. Namely, what's with Winfrey and dieting? Instead of making cruel cracks (on her recent special, Winfrey called the jokes about her weight gain "a national sport" for 25 years), this time there was frustration with what was judged as her obsession with being thin.

But Winfrey maintained that staying healthy was her primary goal.

"This whole P.C. about accepting yourself as you are—you should, 100 percent," she told the Times in 2017. But in that "particular moment in time that I got the call [from WW] I was desperate: What's going to work? I've tried all of the green juices and protein shakes, and let's do a cleanse, and all that stuff. That doesn't work. It doesn't last. What is going to be consistent, keep me conscious and mindful?''

And, Winfrey said, to "all of the people who are saying, 'Oh, I need to accept myself as I am'— I can't accept myself if I'm over 200 pounds, because it's too much work on my heart. It causes high blood pressure for me. It puts me at risk for diabetes, because I have diabetes in my family.''

Oprah Dives Into the Weight Loss Medication Debate

Winfrey continued to speak out on behalf of those who struggle with their weight, knowing how it is to feel like a failure for seeing the number on the scale go up and down and up again.

"You all know I've been on this journey for most of my life," she said during her "The State of Weight" panel on Oprah Daily's "The Life You Want" series last September. "My highest weight was 237 pounds. I don't know if there is another public person whose weight struggle has been exploited as much as mine over the years...This is a world that has shamed people for being overweight forever, and all of us who have lived it know that people treat you differently, they just do."

In her case, she added, "I'm Oprah Winfrey, and I know all that comes with that, but I get treated differently if I'm 200-plus pounds versus under 200 pounds."

Subsequently, she was looking to remove the shame around the topic of obesity and the different ways to combat it, including the use of weight-loss drugs such as Ozempic (a blood sugar stabilizer known as a semaglutide that's FDA-approved to treat Type 2 diabetes).

Doing What It Takes

Winfrey confirmed in December 2023 that she was on medication (she didn't specify which one) to help with weight management.

"The fact that there's a medically approved prescription for managing weight and staying healthier, in my lifetime, feels like relief, like redemption, like a gift," she told People, "and not something to hide behind and once again be ridiculed for."

Her health regimen included regular hikes, drinking a gallon of water a day and eating her last meal of the day at 4 p.m., while still using the WeightWatchers method of counting points.

"I had an awareness of [weight-loss] medications, but felt I had to prove I had the willpower to do it," she said. "I now no longer feel that way."

Leading the Conversation

Winfrey stepped down from the WeightWatchers board of directors in February, but said in a statement she looked forward to continuing to advise and collaborate on "elevating the conversation around recognizing obesity as a chronic condition, working to reduce stigma, and advocating for health equity." (She also said she would donate all the proceeds from selling her stock to the National Museum of African American History and Culture.)

She said in March, however, that she also divested to be able to let the conversation flow freely on her then-upcoming special.

"I decided that because this special was really important to me and I wanted to be able to talk about whatever I wanted," Winfrey explained on Jimmy Kimmel Live. "I did not want to have the appearance of any conflict of interest."

A New Hope

"I wanted to do this special for the more than 100 million people in the United States and the over 1 billion people around the world who are living with obesity," Winfrey opened her March 18 program. "Maybe that's you or maybe that's somebody you love."

"In my lifetime," she continued, "I never dreamed we would be talking about medicines that would be providing hope to people, like me, who have struggled for years with being overweight or with obesity. I come to this conversation with the hope that we can start releasing the stigma and the shame and the judgment—to stop shaming other people for being overweight or how they choose to lose or not lose weight—and more importantly to stop shaming ourselves."

And most importantly, Winfrey concluded, "There is space for all points of view. Let's stop the shaming and blaming. There's no place for it."

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