Oprah shares heartbreaking story about her cancelled talk show

Oprah Winfrey became a star overnight after her self-titled talk show, The Oprah Winfrey Show, aired. A total of 4,561 episodes were produced, and still to this day, memories from the show stick with people.

While Oprah Winfrey didn’t shy away from discussing any subjects on the show, perhaps what happened outside the studio was what touched her the most. In honor of the 39-year anniversary of her first episode, the beloved talk show host now shares a heartbreaking – but beautiful – memory about one viewer whose life changed because of it.

Oprah Winfrey didn’t exactly study to become a talk show host, but it appeared that faith knocked on her door. She landed her first job in journalism, co-anchoring the 6 o’clock headlines on WJZ-TV in Baltimore, Maryland.

However, things weren’t great. Her mentor, who was an editor at work, yelled at her every night she was on the job, and in the end, she was demoted to host a talk show.

“I wasn’t a great writer, I wasn’t fast enough. In the end I didn’t get fired, but I did get demoted to the talk show … which was seen as a big demotion in those days. And that’s where it all began. So, I thank him. He was inadvertently a guiding light!”

Oprah Winfrey began hosting the TV show People Are Talking. While some might not have thought she had the skills to make it work, it was the complete opposite. The talk show became a huge hit, and Oprah had taken her first steps towards stardom.

The Oprah Winfrey Show

Her empathy and courage – trademarks of hers – were the key, and the show lasted for eight years. At that point, a Chicago network wanted her and Oprah was recruited to do a morning talk show called AM Chicago. In 1986, however, the show was rebranded as The Oprah Winfrey Show.

As a young black woman, Oprah Winfrey was a pioneer in the field, and her presence soon turned into what could be referred to as a revolution. On September 7, 2025, Oprah Winfrey reflected on her tenure as a talk show host and the legacy it left behind.

“I knew my life was about to change. What I couldn’t have imagined was the force for good the show would become—the impact it would have on me, on my team (the best team in television), and on the millions of lives we touched,” she wrote.

“If what Maya Angelou says is true—and I believe it with my whole heart—“Your legacy isn’t one thing. It’s every life you touch.” Dear Lord… what a legacy. Even now, people stop me to share what the show meant to them. And more often these days, what it meant to their mothers or grandmothers.”

When she accepted the Cecil B. deMille Award – a Lifetime Achievement and prestigious award for outstanding contributions to the world of entertainment – at the Golden Globes in 2018, Oprah Winfrey talked about the concept of a talk show being more than just a talk show. Rather, she views it as a means of achieving personal healing.

“In my career, what I’ve always tried my best to do – whether on television or through film – is say something about how men and women really behave,” Oprah said in her acceptance speech.

Oprah Winfrey shares heartbreaking meeting with fan

“It’s to say how we experience shame, how we love and how we rage, how we fail, how we retreat, persevere, and how we overcome,” she continued. “I’ve interviewed and portrayed people who’ve withstood some of the ugliest things life can throw at them, but the one quality all of them seem to share is an ability to maintain hope for a brighter morning, even during our darkest nights.”

The Oprah Winfrey Show became a stalwart of TV, attracting millions of viewers. Oprah interviewed more than 37,000 people on her talk show during the 25 years it aired. From average Joes with everyday problems to Michael Jackson, Barack Obama, and Donald Trump.

The Michael Jackson interview actually became one of the most-watched interviews in TV history, with more than 90 million viewers. But while some of the most prominent celebrities all appeared on her show, those weren’t the moments Oprah might cherish the most.

On September 8, it was exactly 39 years ago that The Oprah Winfrey Show aired for the first time. Therefore, the celebrated talk show host decided to walk down memory lane, writing about what actually affected her the most. To this day, people still come up to her, talking about how it affected their own lives. And one story on the show, way back, is still sticking with Oprah Winfrey to this day.

“This past July, I was in Capri at a restaurant that you must visit if you ever go—Da Paolino, ‘the lemon tree,’ as everyone calls it. Under the canopy of lemons, a woman named Sandra, from Boston, came over to my table. She was there with her husband and daughter,” Oprah wrote.

“Marked the beginning of her freedom”

It turned out that Sandra and her sister had watched Oprah when they were 18 years old, and that particular day, sexual abuse was discussed. Sandra and her youngest sister had both been molested, but they hadn’t spoken of it to anyone, nor did they know that the other one had been molested.

Oprah Winfrey continued, “But watching that episode together, they recognized themselves in the story being shared. They started to cry. And then, for the first time, they spoke the truth out loud.”

“That conversation, Sandra told me, changed the course of their lives. She’s now 55. She said that show marked the beginning of her freedom—of speaking her truth. We hugged under those lemon trees, and she left with her family. For days, I couldn’t stop thinking about her,” she continued.

“I regret not getting her last name or number because I wanted to hear more. But I know there are thousands, perhaps millions, of similar stories—moments when something said by me, a guest, or even someone in the audience opened a door that could never be closed again.”

Oprah Winfrey was a pioneer in the television industry. While no one knows how many people she actually helped, either directly or indirectly, through the frame, we don’t know. But what we do know is she made a difference in many people’s lives, no matter how big or small it was.

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