Oprah Winfrey has been one of the most influential public figures in American media for decades. From the launch of The Oprah Winfrey Show in 1986 to her work as a producer, author, and philanthropist, Winfrey has built a legacy that extends far beyond television. Alongside her professional success, she has also been candid about her personal challenges — particularly her long, public struggle with weight.
In recent years, Oprah has spoken openly about using medication to support weight loss and has reflected on how her work contributed to diet culture. She has also acknowledged what she considers her biggest professional regret, a moment that sent a lasting message about body image to millions of viewers.
A Career That Shaped Popular Culture
Born in Kosciusko, Mississippi, Oprah Winfrey began her broadcasting career in local radio and television before moving into national television in the 1980s. In 1986, she launched The Oprah Winfrey Show, which quickly became the highest-rated daytime talk show in the United States.
Over its 25-year run, the program featured thousands of guests, covering topics from health and wellness to literature, celebrity interviews, and global humanitarian issues. Oprah’s influence extended into publishing with O, The Oprah Magazine and her renowned book club, which helped propel many titles to bestseller lists.
Even after the show ended in 2011, Oprah continued to remain active through OWN (Oprah Winfrey Network), her podcast, philanthropy, and numerous partnerships.
The Public Focus on Oprah’s Weight
Despite her professional achievements, Oprah often faced intense scrutiny over her body size. Media outlets frequently commented on her appearance, and she has spoken about the emotional toll of being mocked or criticized.
In an interview with People Magazine, Oprah acknowledged that she felt “blamed and shamed” by public commentary, sometimes appearing on magazine covers that described her with unflattering terms. She admitted that the ridicule was painful and contributed to a sense of internalized shame.
Over time, she also recognized her role in perpetuating aspects of “diet culture.” Through weight-loss specials, makeover shows, and magazine features, her media platforms sometimes emphasized restrictive approaches to dieting. Reflecting on this, Oprah said she now regrets how those narratives may have influenced audiences.
Oprah’s Biggest Professional Regret
One of the most defining moments Oprah cites as her greatest regret occurred in 1988 during an episode of The Oprah Winfrey Show. At the time, she had lost a significant amount of weight through a strict liquid diet combined with exercise.
To illustrate her achievement, Oprah wheeled a wagon onto the stage filled with fat representing the pounds she had shed. The dramatic visual left a lasting impression, but Oprah has since explained that the weight loss was unsustainable. She admitted that she began regaining weight shortly after the broadcast.
Looking back, she said the stunt sent the wrong message — that extreme dieting could provide lasting results. In reality, she explained, it promoted unrealistic expectations for both herself and her viewers.
This realization has shaped how she now discusses weight and health. Oprah has emphasized the importance of sustainable approaches to wellness and the need to move away from harmful diet culture messaging.
Oprah’s Experience With Weight Loss Medication
In recent years, Oprah has been open about using GLP-1 receptor agonists, a class of medications originally developed for type 2 diabetes but also shown to support weight loss.
In a podcast episode, Oprah explained that the medication changed how she thought about eating habits. For decades, she believed that people who stayed thin simply had more willpower. However, after beginning the treatment, she realized that biological factors play a significant role in appetite and weight regulation.
She reported losing about 50 pounds while using the medication, which gave her new insight into how she viewed her own journey and how she perceived others. Importantly, she also acknowledged that medications like GLP-1 are not a “quick fix,” but rather a tool that can help alongside lifestyle changes and medical supervision.
Moving Away From Shame
One of Oprah’s strongest recent messages has been her decision to step away from the culture of shaming that often surrounds body weight. In a 2023 WeightWatchers live special, she admitted her role in amplifying diet culture through her platforms but stated she no longer wanted to participate in that cycle.
Instead, Oprah now emphasizes health, self-acceptance, and compassion. She has encouraged people to understand that body weight is influenced by complex factors, including genetics, environment, and biology, and should not be reduced to willpower alone.
The Broader Impact of Oprah’s Journey
Oprah’s openness about her struggles has had a profound impact on how society talks about body image, dieting, and health. While her early shows sometimes reinforced diet culture, her more recent reflections highlight how perspectives evolve over time.
By admitting her regrets and sharing personal lessons, Oprah has added nuance to the conversation about wellness. She has helped shift the narrative away from shame and unrealistic expectations toward understanding, balance, and compassion.
Her influence also underscores the power of media figures to shape cultural attitudes. The acknowledgment of her regret serves as a reminder that public figures, even those as influential as Oprah, are not immune to reflection, growth, and change.
Oprah Winfrey’s Legacy Beyond Weight
While much of the public focus has been on Oprah’s weight journey, her legacy extends far beyond this subject. She is a philanthropist who has funded educational initiatives worldwide, including the Oprah Winfrey Leadership Academy for Girls in South Africa.
Her book club continues to influence global reading trends, and her work as a producer and actress has earned her numerous awards, including an Academy Award nomination. In 2013, she received the Presidential Medal of Freedom, the United States’ highest civilian honor, recognizing her contributions to media, philanthropy, and culture.
Conclusion
Oprah Winfrey’s story is not just one of fame and success but also of vulnerability, reflection, and growth. Her willingness to admit mistakes and openly discuss her biggest regret — the 1988 wagon stunt — shows how she has evolved in her understanding of health and body image.
Her openness about using weight loss medication and her decision to step away from diet culture highlight an important cultural shift: the move from shame and unrealistic expectations toward compassion and holistic health.
While Oprah continues to be recognized for her achievements in media and philanthropy, her personal journey with weight serves as a reminder that even the most powerful public figures grapple with deeply human struggles. By sharing her story, she has helped reshape the conversation around weight, wellness, and acceptance for millions worldwide.