A Look at Oprah's Complicated, Inspiring Weight Loss Journey Over the Years

Though her exact weight is unknown, based off her weight loss she experienced a couple years later, one can surmise that Winfrey was at or around 200 pounds by the time she was hosting on “AM Chicago” in 1984.

During her appearance on “The Tonight Show” with guest host Joan Rivers, Winfrey was publicly scolded on national television when Rivers told her she needed to lose 15 pounds. Per the New York Post, the famous TV host weighed around 200 pounds at the time.

Prior to her now infamous “wagon of fat” episode in 1988, in 1987, Winfrey appeared on “Dolly” where she weighed a little over 200 pounds. When she began her liquid diet Optifast the following summer, she weighed 212 pounds.

In what became the highest-rated episode in the show’s history, Winfrey wheeled out a wagon full of 67 pounds of fat in 1988 to discuss her weight loss journey and what she did to drop that same amount personally. (If you don’t remember, it was an extreme liquid diet called Optifast.) She would start gaining it back the very next day.

Just one year after that infamous episode, Winfrey admitted on her show that she gained 17 of those 67 pounds back, which served as the impetus for her yo-yo dieting and weight struggles.

In 1991, Winfrey told PEOPLE she’d “never diet again,” reiterating an assertion to made to her TV audience in November 1990, though she didn’t disclose how much she weighed at that time.

In 1992, Winfrey reached her “heaviest point,” weighing in at 237 pounds at 38 years old. That same year, she met personal trainer Bob Greene who would eventually sign on to help get the popular daytime talk show host’s weight under control.

In 1995, Winfrey decided to just “be grateful to her body, whatever shape it was in” and began working out with Greene. That same year, she participated in the L.A. Walk Spring Training alongside Debbie Allen, Dawn Lewis and Florence Joyner.

The following year, she and Greene released a joint book, “Make the Connection: Ten Steps to a Better Body—and A Better Life.” During a press stop at “The Tonight Show with Jay Leno,” she was noticeably slimmer.

In 2002, Winfrey revealed she’d been dealing with heart palpitations for six months and that the grand epiphany to finally do right by her heart and her health hit her in December the previous year.

“I sat up in bed one crisp, sunny morning and made a vow to love my heart,” she wrote in part. “To treat it with respect. To feed and nurture it. To work it out and then let it rest. Since December I’ve kept that vow, and my body has started to redefine itself,” later adding that she’d “finally made peace with my body.”

The peace Winfrey gained a few years prior seemed to finally manifest itself into solid weight loss. Appearing on the January 2005 cover, “The Women of Brewster Place” actress revealed that she’d finally reached a “toned 160" pounds. But things would soon change just a few years later.

In 2007, Queen O was diagnosed with hyperthyroidism and then hypothyroidism — a disease caused by an underactive thyroid that manifested itself with heart palpitations, lethargy, and swelling joints. It also caused her to have a “sluggish metabolism,” fatigue and weight gain.

With that new knowledge in tow, Oprah kept putting on pounds and taking medicine but things didn’t readily improve.

In the January 2009 issue of “O Magazine,” “The Color Purple” star admitted that she’d hit 200 pounds once again but that she’d begun slowly exercising and refocusing on getting a handle on her self-proclaimed food addiction by “eating less sugar and fewer refined carbs and more fresh, whole foods.”

She also came to the realization that she didn’t have a weight problem, she had a “self-care problem,” which manifested itself into her life being out of balance and, subsequently, her weight, too.

In 2015, she finally joined Weight Watchers, of which she credited to giving her “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 also bought a 10 percent stake in the company and came on as a board member. At the time, she also shared that she’d gained 17 pounds due to an ankle injury.

In 2017, Winfrey appeared on the cover of “Weight Watchers Magazine” for the first time ever and shared that through the program, she’d lost 42 pounds.

“At this point I’m wise enough to know that there’s no such thing as failure. It’s all here to teach me. I don’t look at this as a diet; I see it as a plan for life,” she said.

In the years following her 42-pound weight loss in 2017, Winfrey had been consistently slimming down. But it wasn’t until her knee surgery in 2021 that she began being a bit more active by going on hikes for three to five miles during the week and 10 miles on weekends.

She was also still adhering to the guidelines on her Weight Watchers program but admitted to PEOPLE in December 2023 that she had begun taking weight loss medication since July of that same year after her “The State of Weight” panel discussion.

“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, and not something to hide behind and once again be ridiculed for. I’m absolutely done with the shaming from other people and particularly myself,” she said.

That shame seemed to no longer be present anywhere as O was undeniably snatched and cinched during the press run for the 2023 movie musical adaptation of, “The Color Purple,” of which she produced.

As previously reported by The Root, with the willful admission of her using a weight loss drug now taking centerstage, Winfrey stepped down from the Weight Watchers board after 10 years. In the time following, she aired her own special “Shame, Blame and the Weight Loss Revolution,” where she alongside a group of medical experts discussed the popular drugs such as Ozempic, Mounjaro and Wegovy and how to destigmatize the use of them.