Oprah Winfrey’s 40-Year Weight Loss Struggle: Inside the Billionaire Star’s Ongoing Quest for Self-Acceptance


Oprah Winfrey has somehow managed to carve out a private life for herself, despite being one of the most famous women alive.

She goes out with longtime partner Stedman Graham, she and BFF Gayle Kingare nothing if not the picture of vacation goals and, obviously, if you end up on a yacht with Barack and Michelle Obama, Tom Hanks and Bruce Springsteen, long-lens photos will be taken. But for the most part, she has pointedly kept the particulars of her personal relationships largely under wraps. 

Except for one, that is.

Namely, her highly public relationship with her weight. That love-hate relationship has been playing out on TV and the covers of magazines for years.

Even if you’re not a fan of Winfrey for whatever reason (that much success, combined with her longevity, relative ubiquity and her status as one of the most powerful African-American women in the world, in 2017 one of the world’s only two black female billionaires, has certainly made her a target for haters as well), you’re most likely familiar with Oprah’s roller-coaster weight loss journey—which, at this point, is as much a part of her life story as anything.

That story has been told time and again, and it never gets less impressive. Though we’ve yet to check in with everybody, ever, it can often feel as if no one has made more of her life after starting off with less than Winfrey has. Over the course of her career, a trajectory that dreams are made of, Winfrey has simply become one of the most influential personalities of all time. 

Said to be worth roughly $3.1 billion now, her lifestyle rocketed past “attainable” decades ago, but there are countless ways in which Winfrey has endeared herself to people of all ages and from all walks of life—starting with her warm, booming personality that makes you feel as if you’ve known her for years. Then again, we have known the 63-year-old multi-hyphenate for years, be it through her talk show, her magazine, her philanthropy, her cable channel or everything else that made her acting career—which would have been significant on its own—into almost a hobby, something she’s returned to on and off over the years when she felt like it, when the right projects came along as a performer or producer. (We’re in the midst of a scripted-Oprah renaissance, with the recent HBO movie The Immortal Life of Henrietta Lacks and the upcoming big-screen adaptation of A Wrinkle in Time.)

But while she’s never been one to shy away from sharing her life’s considerable low points (they’re part of why she’s such an inspiration to so many), including the emotional effects of crash dieting and her other stabs at rapid weight loss over the years, it’s still hard to picture Winfrey—the queen of self-reliance and self-made glory—not having conquer-the-world-level self-esteem. Because if she’s not living her best life 24/7, what hope is there for everyone else?

AP Photo/Jacquelyn Martin

Yet that’s exactly why Winfrey has been sharing the gritty details of her relationship with food and weight since the 1980s, after she lost 67 pounds with the help of a liquid diet and daily 6.5 mile runs, only to gain it (and more) right back.

At first she tried to make weight loss look, if not easy, then perfectly attainable, pulling a wagon loaded with 67 pounds of gloppy fat behind her on The Oprah Winfrey Show in 1988 on an episode called “Diet Dreams Come True,” a visual that still resonates to this day, while showing off her trimmer figure in tightly belted jeans and a sleek black turtleneck.

But it soon became painfully clear to Winfrey (and subsequently to everyone following along) that maintaining a weight that she found acceptable would end up being a lifelong fixation. She told People in 1991, “I thought I was cured. And that’s just not true. You have to find a way to live in the world with food.” In 1996 she co-authored with Bob Greene A Journal of Daily Renewal: The Companion to Make the Connection, about staying in touch with your body’s needs. Winfrey looked as thin as ever on the cover.

In a 2002 essay for O Magazine called “What I Know for Sure About Making Peace With My Body,” she wrote that she went to her first “diet doctor” in 1977, when she was 23, and “thus began the cycle of discontent.”

“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,” she wrote.  “Although I’d made the connection intellectually, living it was a different story.”

In 2009, a current photo of Oprah shared a cover of O with a photo of a slimmer 2005 Oprah, with the quote, “‘How did I let this happen again?'”

There’s a reason why weight loss is a multi-billion-dollar industry—one that Winfrey herself recently bought into after already having done more for the national diet conversation than almost any celebrity over the past 30 years.

The Journal of Daily Renewal: The Companion to Make the Connection

Hyperion

Just over two years ago, she bought a 10 percent stake in Weight Watchers for $43 million. Strategic business move, sure, but also perhaps an emotional one. According to The New York Times Magazine, the company had extended many invitations to Winfrey over the years to get involved with the company, but it wasn’t until she had gained 17 pounds while nursing a sprained ankle that she decided the timing was right in July 2015.

Weight Watchers’ stock enjoyed a massive Oprah bump and soon “I love bread” was everyone’s favorite new mantra. By September 2016, however, approximately $1 billion that had been gained on paper during those heady early days of Winfrey’s involvement had reportedly disappeared and CEO Jim Chambers stepped down.

But if anyone has learned anything over the past several decades, it’s to never count Oprah Winfrey out. When OWN launched in 2011 it was immediately plagued by stories that it was struggling, plagued by ratings, programming and, summarily, financial issues. And it was plagued by all of that, but by 2013 Team Winfrey had turned it around, thanks to, among other things, a win-win production deal with Tyler Perryand strong ratings for Winfrey’s interview series Oprah’s Next Chapter.

Similarly, Winfrey’s visible presence has since attracted more people to Weight Watchers. Per the NY Times, membership was up to 2.8 million people within a year of Oprah buying in, and stood at 3.6 million by the end of the first quarter of 2017, Weight Watchers’ fourth straight quarter of reported revenue growth. Mindy Grossman, formerly CEO of HSN, signed on as the company’s new chief executive in April.

Oprah Winfrey

Dimitrios Kambouris/Getty Images

Yet all this talk about weight on Winfrey’s part, though nothing new, has generated a new group of critics who don’t think that being skinnier should be on anyone’s list of priorities when it comes to self-worth, and Winfrey’s continued public efforts to look a certain way is sending a distressing and archaic message.

We won’t say those critics are fighting a losing battle, but it’s still an uphill one. Even in this day and age when messages of body positivity, body diversity, acceptance and inclusion are more prominent than ever, there’s a century of misguided precedent when it comes to what people (mainly women) should look like if they intend to look their “best.”

So for now, Winfrey remains a famous voice voicing universal concerns. It’s not as though she only talks about skinny jeans and size 2s. She wants to be healthy and feel good, physically and mentally—and it’s not very sporting of people to suggest that her feelings about her own body are invalid. It’s not right to shame those who would like to lose weight, as though they can’t still be strong or empowered or are otherwise betraying womanhood by wanting to look a certain way, any more than it’s OK to shame someone’s weight in general.

Besides, maintaining a certain weight is important to her. She’s not saying it should be important to everybody.

As an influencer, Winfrey is perfectly aware that it’s not de rigeur to admit you care about what size you are.

“This whole P.C. about accepting yourself as you are—you should, 100 percent,” Winfrey agreed in an interview with The New York Times Magazine. But in response to questions about the prospect of accepting one’s body as it is (whatever that means, really), she explained, “For your heart to pump, pump, pump, pump, it needs the least amount of weight possible to do that. So 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.”

In January, Winfrey proudly revealed that she had lost 42 pounds on Weight Watchers since beginning the program in 2015.

“Before, when I was 150 pounds, I’d imagine getting up to 200 pounds, and think, ‘Oh my God,'” she said in O Magazine. “But now I think, ‘I never thought that at 200 pounds I could look in the mirror and love my body, love myself, not chide and minimize myself for being 200 pounds.’ At 200 pounds, I was OK. I have never, ever, ever been at that point. And then at 190 pounds, I was OK. If I don’t lose another pound right now, I’m still OK.

“The fullness of life, the fullness of being, the self-acceptance—I’d never done that before. I’d always beaten myself up because I was tied to a number.”

Winfrey continued, “When the weight started to come off, I needed to get clear on my intention. I could lose weight to fit a dress size, or attend an event, or to make other people like me. But I couldn’t keep it off for those reasons. I always put the weight back on. This time I changed the intention to, ‘I want to be the healthiest I can be—physically, emotionally, spiritually.’ So the process and purpose of losing shifted for me. It was easier, because my intention was clearer.”

It may not be cool to admit you care about your weight, but it’s real as hell. And honesty remains one of our favorite things.

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Oprah Winfrey’s 40-Year Weight Loss Struggle: Inside the Billionaire Star’s Ongoing Quest for Self-Acceptance

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