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Oprah Winfrey Says ‘Run On’ Was One of Her Biggest Career Mistakes

Oprah​‍​‌‍​‍‌ Winfrey Regrets Releasing Her Only Song


The talk-show TV phenomenon, who is well over 70 years old, is looking back on her failed music venture. When Baby, this is Keke Palmer, went live, she became one of the many voices that came out during that podcast episode, which featured an interview between a 32-year-old celebrity and her. The 72-year-old TV legend also briefly talked to Keke about her first single, which was the theme song for season 13 of her show, The Oprah Winfrey Show, a ballad called “Run On.” She refers to the music of her TV life as “one mistake” in her career and, in fact, as “the biggest.” She further said that in 1999, when the music came out, she was at such a career crossroads. She faced one talk-show option, and she wanted it to be the one she would stick with, for example, starting in 1986, or trying another career. Winfrey says she was praying about everything, and Jesus came to her and literally told her, “You should keep going.” ​‍​‌‍​‍‌

Oprah Winfrey Jokes She ‘Can’t Sing’ After Regretting Music Release

The​‍​‌‍​‍‌ text got Oprah Winfrey thinking about a tune called “Run On”—an old spiritual—which she felt a strong connection with to the extent that she was inspired to come up with a new version of it for herself. Although singing was never really a dream of hers, she decided to go through with it, as that was her instinct at the moment. But that was the only problem? Oprah Winfrey said, We eventually came to the painful realization that I simply cannot sing, even though I had taken singing lessons.”
Palmer did his best to assuage Winfrey, claiming it was not as awful as Winfrey had thought, to which the former talk-show host quipped, “You’re just saying that because you’re looking at me. It was pretty bad.”

In her interview on TODAY, the 2024 Winfrey-Al Roker chat gave her a chance to look back at her triumphs and shortcomings. She also talked of a regret she still had at having to go through a breakup for her talk show in 2011, as per her own admission, which was, I think, “It is wrong; at least it feels wrong if one were to assume that one still continues to end a show and, at the same time, one is trying to put up a network (OWN).” That is one thing; that is my greatest ​‍​‌‍​‍‌regret.”

Oprah Reveals the Career Lesson She Wishes She’d Learned Sooner

“I​‍​‌‍​‍‌ guess I probably did not handle all of that well,” she said. “In fact, I would have finished doing one thing, then taken a year where nothing was really done, and after that, I would have come up with the next thing that was good for me.” She went on to say, “I decided to wrap the show and didn’t go back on my decision. What I now regret is the part where I was doing all of the things together at the same time. I would have done the thing that I tell everyone else to do: ‘If you are unsure about what to do, do nothing. Stay still and do nothing.’ I would have taken that time for myself,” she finished.
After that, Winfrey shared that she had been appreciating even more her quiet times and rests.
She said that the little things bring her the most happiness.
“If it is raining outside on this day, then I am head over heels in love with my life. Do you know why? Because nobody expects you to go out on a rainy day. The day is sunny, and everyone expects, ‘Come on, let’s do this and that and the other. ‘To me, I enjoy the rainy days most. The day is rainy; I have a fireplace, a cozy blanket wrapped around me while a furry dog is lying at my feet, and a fabulous book in hand that I am reading, and I couldn’t ask for anything else. That would be it. That is all for ​‍​‌‍​‍‌me.”

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